From disastrous interrogations to unbelievably stupid "evidence", these downright chaotic trials prove that sometimes, "law and disorder" is a more accurate description of what happens in a courtroom.
1. What A Heel!
At court one morning, the defendant showed up wearing a very distinctive pair of custom-made red cowboy boots... the same boots stolen from the house he was accused of robbing. Yes, he wore them. To court. To plead not guilty. The prosecutor could barely keep a straight face.
2. The Prescription Writing on the Wall
I was involved in a custody dispute. The father claimed the mother was doing all kinds of things wrong and that he should get custody. His attorney questioned the mother about text messages where she appeared to be trying to sell prescription pills. She refused to admit it. It seemed like the attorney had moved on... until he set a perfect trap.
He finally said, “One more question. Where did you get the pills you were selling?” Without thinking, the mom answered, “Oh, my doctor prescribed them.”
3. Ableism In Effect
I was the plaintiff in a tribunal, suing for wrongful termination. My representative asked, “So you fired him because he was ill?” The employer answered, “Yes.” My representative followed up, “And he was ill because he’s disabled?” Again, the employer said yes. “So you fired someone for being disabled?” The employer replied, “Yes.”
4. Justice McServed
A woman wanted me to sue McDonald’s because their employees had beaten up her son. He was trying to rob the restaurant.
Wikimedia Commons, Michael Rivera
5. Snapshots Fired
I once had a client who began his divorce case representing himself before hiring me to take over. To figure out what had already happened, I asked what he had filed with the court. He slid an envelope across the table. I wish I had never opened it. Inside was a stack of photos of his wife, very explicitly posed, taken from close range and showing far more than anyone needed to see.
Yes, the judge saw them. And no, he was not happy. Apparently, my client had discovered that his wife was sending those photos to men online.
6. The Customer Is Always Right
Here’s a clearer, more conversational version with a very similar length and cleaner language:
A woman was involved in a small parking lot accident with a truck at a casino. Someone told me she parked afterward and went into the casino for a few hours. But during her deposition, she claimed she was in so much pain that she went straight home and then to the hospital. So I asked whether she visited that casino often and whether she had a rewards card.
She was glad to say yes. She even told me she had gold status and showed me the card. That ended up being a major mistake. I subpoenaed the rewards card records, and they showed she had been playing slot machines for hours after the accident.
7. I Haven’t Got You, Babe
I used to work in paternity court as a caseworker. This man kept insisting to me, the child’s mother, and anyone else who would listen that the baby was not his. When they finally appeared before the judge, DNA testing confirmed that he was not the father. The guy immediately took off his jacket. Underneath, his shirt said, “NOT THE FATHER”!
8. Spoiler Alert Will
The two sons of a very wealthy couple went to the family lawyer to hear the reading of their recently deceased parents’ will. The lawyer was extremely nervous because he had known both of them since they were kids...and he was about to reveal the family’s biggest secret. One son received the entire inheritance, while the other got nothing.
The reason given was that the money should go only to blood relatives. That was the day the second son found out he had been adopted.
9. Well, I Guess He Walked Right Into That One...
My dad, who is a lawyer, once had someone come in claiming he couldn’t walk because of a workplace injury. My dad was suspicious, so he hired a psychologist to examine him. She concluded that something might be wrong, but she couldn’t say exactly what. Then the next week, my dad got a video showing the man walking down his driveway to take out the trash.
That was the end of that. My dad called him and said, “Come on in, we’ve had a breakthrough in your case, and you may be able to recover some money for your injury.” The man came to the office, and my dad left him waiting in the lobby for almost an hour because he knew the guy was just trying to scam his way into a payout.
Eventually, my dad brought him into the conference room and played the video. The man got up and left.
10. No Parting Gift Like One Last Miff
I’m a lawyer, and I thought I had seen everything, but this brutally honest will surprised even me: “To my wife I leave her lover, and the knowledge that I was never the fool she believed me to be. To my son I leave the pleasure of working for a living—for 25 years, he thought the pleasure was all mine.” Absolute all-time insult.
11. A Love-Hate Relationship
My client was accused of refusing to leave a woman alone after she said she wanted no contact with him. He insisted they were in a relationship and said she only called the police when they argued. She insisted she wanted nothing to do with him. She even had a photo on her phone of him sitting on her porch as proof that he had shown up without her permission.
I asked the judge if I could look at the photos right before and after that one for context. Sure enough, she had hundreds of pictures of him—having dinner with her, sitting on her couch, even wearing her underwear. It was a very satisfying moment.
12. Salt Of The Earth
Lawyer here. I once updated a will for a doctor who decided to cut his son out by removing everything he had planned to leave him and replacing it with a “manure spreader.” I didn’t ask questions, because changing a will is usually straightforward. But someday that doctor will die, and his son will basically be told to go kick rocks.
13. Surprises Comes In Twos
My estate planning professor told us about a man who had two separate families, and neither knew the other existed until it was time to read his will after he died. This wasn’t a mistress or secret-child situation—both were full families with multiple kids. Both families showed up for what must have been one of the most uncomfortable will readings ever.
I still have no idea how he managed it, except that he traveled often for “business.”
14. That’s Just Wrong
My ex’s brother helped a friend of his—he knew both spouses, but clearly took the husband’s side—hide assets and launder cash during the six months leading up to a sudden “I’m divorcing you” announcement. The wife, now deceased, had just been diagnosed with cancer and was not expected to live.
He apparently felt that “his money” shouldn’t go toward “her medical care” if she was only going to “die in a few years” anyway.
15. Feeling Bad For The Children
I’m an attorney and a foster parent, and my wife refuses to sit next to me in court for our kids’ cases because I usually whisper a running commentary about how bad some of the lawyers are. The judge in these cases knows me and knows I’m an attorney, so he finds it amusing. The last time we were there, one particular lawyer—my absolute favorite—was handling the case before ours.
The judge, every other attorney, and I all dread dealing with her because she is clueless, loud, and incompetent. So she stands up and says, “Your Honor, my client has only been found guilty of child endangerment in another county. I don’t see why this court should hold that against him in deciding custody of his children.” The judge was not persuaded.
16. Doesn’t This Guy Have Anything Better To Do?
My parents are lawyers, and they told me about a divorce case where one of the biggest fights was over a car. For months, the husband kept saying he would never let his wife have it. Eventually, though, he gave in and agreed to hand it over in exchange for something major, like one of their summer houses.
Later, it came out that he had been driving the car in a huge loop around the city for three hours a day, every day, piling on thousands and thousands of miles and basically ruining its value. The amount of planning and pure pettiness behind it was honestly incredible.
17. There's Always A "But"
There was a man trying to get custody of his children after a divorce, while his wife was accusing him of physically harassing her. He was asked whether he had ever laid hands on his wife, and he flatly said, “Yes, but only when she annoyed me.” I had to try very hard not to laugh in the courtroom.
18. The Self-Fulfilling Defense
I’m studying law right now, and one of my tutors told us about a case from when he worked for the state. The defendant tried to argue that being an orphan had caused him severe PTSD and mental illness, making him unfit to stand trial. The problem was that he was on trial for murdering his parents, so the argument didn’t exactly hold up.
19. Told You So
I was in court once, and the case before ours was dragging on way longer than expected. The defense lawyer made a motion to dismiss, saying there wasn’t enough evidence. The judge said he would consider the motion after lunch, banged the gavel, and said court would reconvene at 1 p.m., then added, “Court dismissed.” The defendant stood up and shouted, “Told you I could get away with stealing that stuff!” He thought the judge meant his case had been thrown out.
20. Better Taxidermy Than Estate Tax, Am I Right?
In my trusts and estates class in law school, we read a case about a man who left everything to his wife, but only on the condition that she had his body stuffed and kept on the living room couch forever. Fortunately for her, the court threw out that part of the will. If I remember right, part of the reasoning was that it would make dating or remarrying pretty much impossible if her husband’s preserved body was sitting there staring at every visitor.
21. The Beauty Of The Bodycam
I represented a client who was arrested for driving under the influence, and he insisted over and over that he had not been drinking. The stop involved a rookie officer who had his field training officer riding with him. The rookie pulled my client over for an issue with his tags, then walked back to the patrol car with his body camera still recording. The audio went like this:
The training officer said, “Book him.” The rookie replied, “But he’s not intoxicated,” and the training officer answered, “Do it anyway.” Then the body camera was turned off. Seven minutes later, it came back on, and they were giving my client field sobriety tests. My client spent three weeks in custody before I finally got the footage from the prosecutor and showed it to the judge.
The prosecutor’s expression when the judge watched that video is something I will never forget. The judge sent a letter to the police chief saying the training officer’s career was finished, and that he would deny any future search warrants that officer tried to bring.
22. Maybe They Just Had A Question!
Two men were on trial for robbing a gas station. A customer who had witnessed the whole thing was on the stand. The prosecutor asked him to explain what he saw. He said he saw two men rob the store and run out, and that one of them bumped into him on the way. Then the prosecutor pointed toward the defense table and asked, “Are those two men in the courtroom today?”
At that point, both defendants raised their hands. That was the end of that.
23. A Hole In Logic
My firm had been trying for years to collect a six-figure judgment from a woman. She kept very little in her personal bank accounts and instead used business accounts to support a very expensive lifestyle. She constantly claimed she was broke and said she did not use company money for personal expenses, including in sworn court filings.
During her deposition, she said she was up to date on the mortgage for her large house. We spent hours going through her finances, and then I returned to the mortgage issue and asked, “If you’re broke but current on your mortgage, how are you making those payments?” Her face immediately went pale. There was complete silence, and then she quietly said, “I use company funds.”
Her attorney stopped the deposition right there and took her out of the room. My boss started laughing and told me it was an excellent question.
24. Race To The Finish
I’m not a lawyer, but I do have a story connected to a divorce case. I used to work on banking equipment, and one of my favorite jobs was opening safety deposit boxes for banks. One morning, I was asked to arrive before the bank opened, which was unusual. When I got there, I met a bank employee, a lawyer, and a very angry woman. She was clearly in a hurry to get into the box.
I opened the lock and pulled the door open, and she shouted, “Let me in there.” So I stepped aside and let her rush past. A moment later, I heard a stream of angry shouting. The box was empty. Then she stormed out, and as she passed, she threw down a single sheet of paper that had been left inside. It basically said, “Nice try.” It had been a bitter divorce, and her ex-husband had gotten there first.
25. All My Fingers and Toes
There was a man who had cut off all of his fingers. He was clearly dealing with a very serious mental illness, maybe schizophrenia or psychosis, though I never learned the full story. One night, he decided that a way to get money would be to break into a butcher shop and use a meat saw to cut off all his fingers and both thumbs at the knuckles, which is exactly what he did.
He was found the next morning and somehow survived. He was placed in a mental health facility and made an almost complete recovery, except for the loss of his fingers. Later, he wanted to sue someone. He did not really know who he wanted to sue. He just seemed convinced that if he had been injured, he should get compensation. I remember his main question was whether he would receive more money if he went back and cut off his feet too.
26. Occupational Hazard Lights
I represented a man whose car battery died in the middle of the freeway at 4 a.m. He turned on his hazard lights and called 911 for help. Around the same time, an LAPD officer in an unmarked car was driving at a fairly high speed. He didn’t see my client, hit him, and caused a serious six-car crash, including an overturned 18-wheeler.
When investigators arrived, they took photos of the scene. The LAPD officer claimed my client didn’t have his hazard lights on and said he was driving more slowly than we alleged. In other words, he was trying to shift some of the blame onto my client. During the deposition, the attorney brought out the scene photos. One of them clearly showed my client’s hazard lights on. Not long after that, the case against us was dropped.
27. But You Forgot To Ask About This
In a deposition, it’s the questioning lawyer’s job to ask the right questions and be careful and systematic. If they fail to ask about something, that’s on them. Lawyers defending a witness always instruct them not to volunteer extra information and to answer only what is asked. Again: don’t volunteer.
I once had a witness come in, and we went through the full prep session. I gave her all the usual instructions and specifically told her not to volunteer anything. We got through the deposition, and she did well. The questioning lawyer had finished, was putting away his papers, the court reporter was packing up, and he was heading for the door. That’s when everything went wrong.
Out of nowhere, the witness said, “Did you want to see this?” and pulled out a stack of books no one had asked about, she had never mentioned to me, and that contained material the other side was then able to use.
28. Dear Diary...
I worked on a harassment case involving a plaintiff who had been paid to role-play with her boss and kept a very detailed diary of their encounters on her work computer. At one point, she was asked to read part of the diary into the record. She was asked several times whether she wanted her new husband to step out of the room while she did so, but she said no. That turned out to be a very bad decision.
Let’s just say the content was highly explicit. She confirmed it was accurate, and the only mention of her current husband was that she found him unexciting in bed but planned to marry him because her first three choices hadn’t worked out. He eventually walked out on his own after hearing that passage and confirming she was talking about him.
29. Gordon Ramsey’s Idiot Sandwich
A few months ago, I had a case where a man was charged with shoplifting. He turned out to be 70 years old, with no criminal record at all, and the item in question was a sandwich he had calmly eaten in the store. He genuinely believed he had already paid for it. I was upset that charges had ever been filed. When I saw him in court, he was clearly frightened.
I dismissed the charges right away and wished him the best.
30. Hold Your Temper
I was taking my ex to court over custody of my child. I had put together a 150-page file that included a child protective services report, because there had been harassment in the home, along with text messages and plenty of supporting records. My ex chose to represent herself, apparently out of overconfidence.
Before the hearing began, she offered me a proposed agreement that would have given me custody while also including some fairly generous terms for herself. I politely declined, because we believed we would receive much more at trial. The case was called, testimony was given, and she put on one of the most chaotic and self-defeating performances I’ve ever seen in court. During her closing statement, she tried to hand the judge the agreement she had offered us. The judge refused to accept it.
“You can’t just hand me documents. That’s not how evidence is submitted. I’m not reading that.” She started arguing with the judge, shouting, and completely losing control. In the middle of the confusion, she said, “And this agreement gives him custody, which is one of the things he wants!” apparently trying to show she was being reasonable.
My lawyer quickly jumped in: “So you agree that the father should have full custody?” In the heat of the moment, she shot back, “Yes! That’s what I agreed to!” Our side immediately went silent, and after working to calm her down, the judge issued his ruling. It began by granting me custody and ordering therapy for her.
She essentially gave up custody of her daughter in the middle of an argument with the judge.
31. That Settles It!
I was at a hearing arguing that my client had been wrongfully fired because the employer didn’t follow the proper procedures. During the hearing, one of the employer’s witnesses tried to submit documents that had clearly been altered to make it seem like everything had been done correctly. It was an open-and-shut case.
I spotted the changes and was getting ready to point them out when the other lawyer realized what had happened, quickly pulled the witness out of the room, and after a short break, offered my client a large settlement.
32. The Test
Picture this: a mother and father are in a custody dispute. The mother isn’t making much money, but she’s working hard to support her kids. The father is lazy. He was actually supposed to have primary custody, but he disappeared, so she’s been caring for the children for a couple of years and now wants primary custody officially transferred to her.
He’s fighting it out of pure self-interest. In many places, when a child is involved, the court appoints a guardian in addition to the lawyers for each parent. The guardian speaks with both parents, interviews the child, does some basic investigation, and gives the judge their recommendation.
In this case, the guardian said plainly that the mother was probably the better choice, but suggested both parents take a substances test just to be safe. The judge agreed and sent them off to be tested right away. Once that was done, everyone came back to the courtroom, where the judge read the results. Even I was surprised.
The mother tested negative for everything. The father tested positive for a certain powdery substance. The mother got full custody.
33. Lawyers Can Go Mad, Too
I worked at a firm that was subpoenaed during a divorce between a partner at our firm and a partner at another major firm. The woman sent out more than 70 subpoenas to banks, law firms, investment companies—you name it—because she was convinced he had hidden more than $20 million overseas without telling her.
It got so extreme that she dug up receipts from 25 years earlier to try to piece together this huge conspiracy. But there was one thing she hadn’t considered. In the end, after running up $1.5 million in legal fees and going through seven different lawyers, the judge said enough was enough—there was no conspiracy, and she was not entitled to any share of this imaginary $20 million.
Keep in mind, this was a partner at a major firm acting this way. She made millions a year in her career. But she seemed to completely lose perspective.
34. Easy Peasy
My wife is a lawyer. Once children become adults, if they stop studying and start working, child support usually no longer has to be paid. My wife’s client had found a new partner, which set off his ex-wife, and she started asking for more child support for their children. To win the case, we needed to prove the children were working, but we couldn’t find any proof.
There didn’t seem to be much chance of winning, but we still went to court, hoping the questioning might bring out something we could use as evidence. Then, on the day of the trial, the children didn’t appear—only the mother and her lawyer were there. The judge asked, “Tell me why your children couldn’t come.”
The mother answered, “They couldn’t get permission at work.” Everyone went quiet. The judge, the lawyers, the mother. After a few more seconds of silence, the judge said, “Well, that was quick.”
35. A Post-Mortem Addition to the Family
I’m a lawyer who works with wills and estates. I was helping a kind older woman when she suddenly revealed something major. She told me she had a secret daughter, and she wanted to leave her some money and photographs without the rest of the family finding out. Even her husband didn’t know about the child. That will certainly be an interesting conversation after she passes away.
36. The Wedding Photographer
I represented the husband in a divorce case. On the day of trial, opposing counsel introduced some truly shocking material. The wife’s attorneys brought out photographs they said proved adultery. The pictures showed my client—the husband—wearing lingerie and a long brown wig, being intimate with another man. I was able to keep the photos out of evidence… because the wife had taken them herself.
37. But It's My Favorite
This was literally the first thing I ever did as a law student intern. My client had a solid defense in a possession case. Substances were found in a jacket, but my client wasn’t wearing a jacket, so it was going to be very hard for the prosecution to prove the jacket was his. I spent a long time with him explaining all of this, and he was thrilled.
Then on the day of the preliminary hearing, he walked in and sat directly in front of the officer who had arrested him… while wearing the jacket in question. The exact same jacket we were planning to argue they couldn’t prove belonged to him.
38. Learning To Fall
Years ago I worked in personal injury, and a woman came to us claiming she had slipped and fallen outside a nail salon because they hadn’t cleared away the wet leaves by the entrance. So we took the case, and almost right away opposing counsel called to say he was sending over something important. When we opened it, I could barely believe it.
We put the disc into the computer, and there was security footage of our client picking up the wet leaves, placing them on the sidewalk, and then sitting down on them before calling for help. I have never wanted to bury my face in my hands so badly. Needless to say, we dropped the case.
39. Who Needs Probation Anyway?
A judge was making a group ruling for several people about probation in cases involving impaired driving. The judge asked the room, “Has anyone consumed or taken any substances in the last 24 hours?” One man proudly raised his hand and said, “I used illicit substances last night.” That one man did not get probation.
40. The Devil Is In The Details
I was trying to get a restraining order in divorce court for a woman against her son’s father. She told a story about him grabbing her arm and slamming it against the tub, breaking her wrist. During cross-examination, I asked the accused—her ex—whether he had ever intentionally broken my client’s wrist. Then the full and awful story came out.
His response: “Oh yes, I did.” I was thrilled… for about two seconds. Then he continued: “She was nine months pregnant and about to use illicit substances. I tried to grab her arm to take the pipe away and protect my unborn son.” She had left that part out when she spoke with me.
41. You Had One Job
We had a client who served on a company’s board of directors and was being sued for allegedly failing to inform the board about something important. A few other attorneys and I spent an entire week preparing him for his deposition, reviewing every document in the case and explaining why each one mattered. We repeatedly told him that, whatever else happened, as long as we could show he had told the board about this one issue, he would be okay.
The day of the deposition arrived, and it quickly went off the rails. Opposing counsel sat down and started asking questions, and we thought we were in great shape. All our client had to do was say he told the board this one thing. Within the first 5 to 10 minutes, opposing counsel directly asked him what he had told the board. Our client answered, “I told them about Y, I told them about Z, I told them about A, B, and C.”
He said absolutely nothing about the issue he was actually being sued over, the one thing that mattered most in the case against him. In more than 20 years of practicing law, it was the closest I’ve ever come to wanting to walk away on the spot.
42. Going A Little Too Far With The Story
I was sitting in court waiting for my case when a basic traffic stop matter was being heard. The prosecutor had the officer walk through what happened. The officer gave a very detailed account of pulling the driver over for running a red light and then noticing a broken tail light. He described how he stayed calm and professional, even while the driver became angry.
According to the officer, the driver was swearing at him and saying he could “shove the ticket where the sun doesn’t shine.” The officer then said the driver tore up the ticket and threw it at him. He told the story so convincingly that everyone in the courtroom seemed drawn in. The driver was not a lawyer, but he chose to represent himself and needed only a minute to completely undercut the officer’s testimony.
“Your Honor, the officer testified under oath that I acted belligerently and then aggressively tore up and threw away the ticket, which I find difficult to believe.” He paused for effect, then delivered the key point: “Because this is the ticket, still in one piece, without even a crease on it.” He pulled it from a folder in front of him.
You could hear people in the courtroom gasp, laugh, and whisper. The judge stopped the driver, looked at the prosecutor, and without hesitation the prosecutor said, “We would like to dismiss the case.” All the other defendants waiting for their cases started applauding.
43. Maybe She Just Forgot
It was a custody dispute. The mother’s lawyer put her on the stand mainly to help establish her credibility. It fell apart almost immediately. During cross-examination, the opposing lawyer asked about an allegation that she had smoked substances with her children when they were 12 years old. The mother said the children were lying and tried to shift the focus to the father’s so-called “harassment,” which, for the record, did not exist.
In that same cross-examination, the mother admitted to “medicinal usage.” When asked for details, she acknowledged she did not have a card, and when asked where she got the substance, she said, “the local dispensary down the street.” At that point, her credibility was gone. Keep in mind, her own lawyer had put her on the stand specifically to make her seem like the more trustworthy parent. It could hardly have gone worse.
44. Photo Finish
I was involved in a civil case against an organization that had tried to cover up battery and molestation involving a vulnerable population. During a deposition, opposing counsel launched into a very aggressive series of questions, accusing the person being deposed of making false reports in the past and having convictions for forgery and identity theft. Our client calmly answered “no” to about a dozen of these questions. Opposing counsel became increasingly hostile and even threatened to bring out mug shots at trial.
Then he pulled out a photo and suddenly went pale. It was a picture from his own file, which he held close to his face before quickly putting it away and abruptly asking to end the deposition. It turned out he had pulled records for the wrong person. I later learned who that other person was, and although they had the same name, they were more than 15 years apart in age.
45. The Others
I had a family law client whose ex was preventing him from seeing his child. We were in court while he explained how much parenting meant to him and how deeply he loved being a father. I was in for a very unpleasant surprise. After about 45 minutes of this, the mother said, “I don’t know why he’s saying all this. He abandoned his other kids.”
That was news to me, because he had never mentioned having any other children. As it turned out, yes, he had completely abandoned them. He had not been in contact for years and had made no effort to be involved in their lives. Please tell your lawyers the important facts, especially when the other side already knows your secrets.
46. Not Reading The Room
My law professor once defended a young woman facing substance charges. In court, his strategy was simple: tell the truth. Her life had gone downhill because of trauma, but she was now in a stable, loving relationship with another woman. For the first time in a long while, she had some peace and security, was honestly trying to turn her life around, and seemed very unlikely to offend again.
It was hard to predict how the judge would take that, until the prosecutor stood up and started attacking the two women. He argued they were lying because “lesbian relationships aren’t real.” According to the professor, “everyone in the courtroom except the prosecutor knew the judge was gay,” so that did not go over well.
The judge sharply reprimanded the prosecutor, delivered an angry speech about gay rights, and ultimately gave the woman a very light sentence, along with kind wishes for her future with her partner.
47. Chicken Run From Dad
I was representing a mother in a nasty custody battle. The father wanted full custody and claimed the mother was unfit. The mother wanted full custody because the father had a history of domestic violence against both her and the children. During cross-examination, the father’s lawyer was doing a solid job of making her look bad, and I was starting to get nervous.
Then his lawyer called a close family friend as a character witness, and the friend said all the usual positive things about the father. At one point, though, he mentioned that they owned chickens. That struck me as strange, so I started asking follow-up questions. Before long, everything came out.
I got the friend to admit that the father kept chickens for fighting and took his underage children to those fights.
Worse, when the children misbehaved, he punished them by making them feed the chickens, which meant they got pecked and scratched by these aggressive birds. The children were clearly terrified of them. I could actually see the father’s lawyer go pale. The mother got full custody.
48. All He Had To Say Was Yes
I handle landlord-tenant cases, and my client was being evicted for nonpayment of rent. But the client had been withholding rent because the apartment had serious habitability problems: no heat, dangerous lead levels, and vermin. I thought it was going to be an easy win. I kept telling my client not to spend the money and to hold onto it.
If you can show the judge you still have the rent money, it makes you look much more credible and supports the argument that you were withholding payment for legitimate reasons. We go before the judge, and the landlord doesn’t even have a lawyer. Internally, I’m thrilled. I’m thinking there’s no way I can lose. I was completely wrong. I made my arguments, and the landlord made his.
Then the judge asked my client whether they still had the money. My client said, “No, I spent it all at the casino last week.”
49. Absolutely Evil
She took the cats. He wanted the cats. It looked like the court was going to award him the cats. She had them euthanized.
50. Never Fear, Grandma's Here
This was a custody dispute in a jury trial. We represented the father of young twins, and the mother was seeking child support. The key issue was that, for the previous three years, they had shared the children exactly 50-50. He had one weekend, she had the next, one parent had Monday and Tuesday, the other had Thursday and Friday, and they split Wednesday.
She believed she could get more. The problem was that she didn’t really have a case. Before trial, she kept taking the kids to CPS and child psychologists in an effort to create a basis for primary custody, but we got all of that excluded. So on the day of trial, she finally unveiled her main argument: the children had asthma. She claimed it was serious enough to require special equipment, and that the father was ignoring it. In her view, he was negligent, putting them at risk, and she should have primary custody.
Overall, the trial was going in our favor. She wasn’t a strong witness, and she had no medical records to support her claims. But the moment that really settled it came when she called her final witness: the children’s grandmother, her own mother. The jury already knew that Grandma babysat the kids, and the mother had insisted that Grandma’s apartment was not a dangerous place for children with asthma.
But when Grandma took the stand, she leaned into the microphone and cleared her throat. “Ahecchhhmm.” It was deep, wet, and unmistakably the sound of someone who had spent decades smoking heavily. You could hear it in every word after that. After only half an hour of deliberation, the jury awarded primary custody to the father. He burst into tears right away, while the mother just sat there without moving. It was the right outcome.
51. Hide And Go Seek Gone Wrong
I’m an accountant, not a lawyer. I had a client whose divorcing husband hid Ziploc bags of ground meat all over the house—inside air vents, up in the attic, behind the water heater, and more. I think there were at least 20–30 bags, and it took months to find every single one.
52. Domestic Stupidity
I used to advocate for domestic violence survivors and helped victims get protective orders against their abusers. At one hearing, my client told the court how he hit her after an argument. The judge asked him, “So, did you hit her?” He replied, and I quote, “Now Judge, it was just a little love tap, you know how it is.”
The judge blinked twice, stunned, slammed his gavel, and granted her petition.
53. A Boneheaded Play
I sat in on a personal injury case where the plaintiff broke her leg in an accident, and a doctor testified as an expert witness. The woman’s lawyer started asking the doctor about his experience with leg injuries—he was a well-known orthopedic surgeon in the area. She asked whether he had ever treated a tibula fracture. He simply said, “No.”
So she started pressing him with more questions about the tibula. After six or seven questions, she finally asked, “How did you get a medical license if you’ve never treated a tibula fracture?” She launched into a long rant trying to discredit his qualifications, and he calmly replied, “There is no bone called the tibula.”
The lawyer turned bright red, and everyone in the room tried their best not to laugh, including the judge.
54. Thank The Lord
I had a client argue that she didn’t owe the credit card company because of Jesus. True story. Her basic argument was that debt is a sin—or maybe not paying it was the sin. Either way, her reasoning made no sense. And since Jesus died for all our sins, she argued that Jesus died to pay off her debt. She was clearly not thinking straight, but I have to admit, it was oddly creative.
55. The Facepalm Hall Of Fame
I work in a judge’s office as a public servant, and since I have a law degree, I sometimes sit in on hearings with the judge. Last month, we had a major substance trafficking case—more than 20 people involved, months of investigation, undercover agents, video, audio, the whole thing. The hearing lasted three days.
Then it was time for one of the defendants to take the stand so the prosecutor could read the charges against him. The prosecutor said he was accused of selling, trafficking, and carrying a certain amount of illegal substances, and that his house—where he lived with his partner—was the base of the operation. Then came his response. He immediately said, “Wait, I was the one selling. She didn’t do anything.”
His lawyer buried his face in his hands so hard you can actually hear it on the hearing audio. He still pleaded not guilty.
56. Now This One’s Just Cheesy...
My dad is a lawyer, and one time someone came in wanting to sue McDonald’s because her cheeseburger was placed upside down in the bag instead of right side up.
57. The Value Of Silence
Lawyer here. During an order of protection hearing, a 6'3", heavily tattooed guy told the judge that my 5'1" female client deserved the black eye he gave her because she wouldn’t stop talking back. He actually seemed to think the judge would understand. The moment he admitted he hit her, the judge cut him off and said, “Order of protection granted. Next case.”
58. Some People Are Heartless
It was a difficult separation. The wife filed a restraining order against the husband, which is pretty common. He wasn’t the worst person, but he wasn’t great either. About a year into the divorce, his mother was dying, so he asked his sister to speak to his ex-wife and see if she would bring the kids to visit her in the hospital before she passed. She didn’t. Instead, she went to court and said he violated the restraining order by trying to contact her through someone else.
He admitted it and explained why, but the court still found that he had violated the order. His mother died while he was in custody, and the wife never brought the kids to see her.
59. They’re Reaching, Your Honor
I’m not a lawyer, but when my mom was hit by a drunk driver, we filed a wrongful death suit. The defense lawyer argued that because my mom had cancer, she was going to die anyway, so no compensation should be owed.
60. The Polygamist Without A Brain
I had a client who was trying to get away from a terrible ex and filed for a restraining order. The ex showed up to the hearing and made a huge issue over a truck they bought during the marriage. He said it was his, and that she had no claim to it because their marriage was invalid. That immediately caught my attention. During cross-examination, I asked what he meant, and he said he had already been married in another state when he married my client.
He said my client had no idea, but that it meant the marriage wasn’t valid and the truck belonged entirely to him. Not only was that wrong, but he clearly didn’t realize how much trouble he had just created for himself. We quickly turned the hearing transcript over to the authorities, who were already investigating him for bigamy. All over a truck.
And for the record, my client kept the truck.
61. I’m Taking Mew With Me
I worked with a client who wanted her cats euthanized and buried with her. We had to explain that we legally couldn’t include that language. The ethical side of it didn’t seem to register with her. She’s one of the few clients who ever really got under my skin.
62. What If That Was A Lie?
At my first jury trial, I was cross-examining the alleged victim, and in response to one of my questions she said, “Oh yeah, I lie all the time!” Needless to say, I won that trial.
63. No Prompt Needed
I had to cross-examine a custom home builder who claimed he had put more labor and materials into a house than the contract required, and he was suing to recover those extra costs. I was asking him about an email exchange with my client over the construction price, and he admitted he knew he couldn’t build the house for that amount. That’s when my head snapped up.
The supervising partner’s head snapped up too, and opposing counsel went pale. At that point, I knew exactly where to go. Me: "You gave that price quote?" Builder: "Yes." Me: "You knew you couldn’t build it for that price?" Builder: "Yes." Me: "You knew the homeowner was relying on that quote?" Builder: "Yes." Me: "You knew the homeowner wouldn’t have signed the contract without that representation?"
It was basically textbook fraudulent inducement, and he had no idea what he’d just admitted. I couldn’t believe it. The builder got thoroughly dismantled in arbitration and was hit with substantial punitive damages on top of that. Five minutes of testimony sank his entire case because he volunteered damaging information without being asked. Some people really do surprise me.
64. Sweet Revenge
A wife cheats on her husband while he’s frequently away for work. She files for divorce and gets to keep the house. Months go by, and the husband is still understandably furious but has no real recourse. Then he has a realization: “I wonder if she changed the password to the Nest thermostat?” She hadn’t. For the next year, he keeps messing with it.
In the middle of summer, while they’re sleeping in his old bed, he turns the heat up to 90 degrees at 3 a.m. In the middle of winter, he shuts the heat off and hopes the pipes freeze. If they go on vacation, he turns the air conditioning down to 55 and lets it run nonstop, setting them up for a brutal utility bill when they get home.
65. One Flew Over The Solicitor’s Nest
I work with estates and trust accounts. Once, I had to open a trust account under extremely unusual circumstances. It was a multi-million-dollar trust for a single beneficiary, the deceased couple’s son. But here’s the disturbing part: the reason the parents were dead was that the same son who inherited the trust had killed them...with a hammer. He had pleaded insanity.
Once a year, he would call from the prison psychiatric hospital asking for $50 in commissary money to buy snacks and gum. The calls were always unsettling. He was very polite, very medicated. The audio always sounded oddly tinny, like he was calling from very far away.
66. Mistaken Identity
When I was in law school, I clerked for a defense clinic. We had an assault and battery case where the only witness was the alleged victim. I was sitting at the defense table with the attorney, another law student on the case, and the defendant. By pure coincidence, we were all wearing similar-looking suits.
The victim was asked in court to identify the person who committed the assault. She pointed to me instead of the defendant. Our attorney asked several times whether she was really identifying me and whether she was sure, and she said yes each time. The prosecutor looked stunned, and the trial more or less ended there, since it was a bench trial rather than a jury trial.
No one ever said it outright, but I’ve always suspected our attorney wanted me at trial because I bore a passing resemblance to the defendant.
67. Telling On Yourself
My parents own a jewelry store, and their landlord was pressuring them to sign a lease at almost double what the appraiser said it was worth. The problem for him was that their original lease said that when it came time to renew, each side would hire its own appraiser and then settle somewhere between the two values. But the landlord didn’t like what his appraiser came back with, so he refused to tell my parents the real number.
For two years, he hired just about every lawyer in town to try to force my parents out. They tried everything, but legally they didn’t have much to work with. During that time, unfortunately, the landlord developed Parkinson’s, and his mental state began to decline. Eventually, we got him to sit for a deposition, and that’s where everything fell apart for him. It was like he suddenly decided to tell the whole truth.
My parents’ lawyer would ask questions like, “Why didn’t you show the appraisal to my clients?” and he’d answer, “Because it wasn’t what I wanted. I wanted them to pay more, so I hired other appraisers and paid them to push the price up to nearly double.” By the end, his own lawyer had his head in his hands. Within a month, my parents had a new lease for less than they had originally offered, and the landlord had to cover 75% of their legal fees.
68. Lying For The Cheating
When I worked in insurance defense, I handled a case where a man reported his Rolex as stolen. He insisted he had been staying at a hotel when it disappeared. The problem was that he had no proof he had ever been at a hotel during that time. We went through the whole process and eventually reached depositions. Once he was under oath, he finally admitted where he had actually been.
He wasn’t at a hotel. He was with his mistress, and he had accidentally left the watch at her house. His wife noticed he wasn’t wearing it, so he immediately claimed it must have been stolen, and the whole story snowballed from there. Yes, this man hired an attorney and went through the entire process just to keep his wife from finding out about the affair. Needless to say, we denied the claim.
69. By Alien Design
My father is a patent attorney, and when I was about 14, he told me about a man who wanted to patent the iPhone 3 because he believed “aliens” had given him the design.
70. Radical Honesty
My friend’s mom was a defense lawyer for a hospital. Her job was to represent doctors accused of malpractice or other issues involving doctor-patient interactions. She had one case where a female patient accused a male doctor of touching her inappropriately several times during a procedure. It was deeply upsetting. Apparently, the doctor had been coached to say that he might have accidentally brushed against the patient’s chest, and that if it happened, it was an unintentional result of following standard procedure.
Then they got to the deposition, and from what I heard, one of the first questions was something like, “Walk me through what happened.” The doctor responded, “I don’t know what you want me to say. I’ve always been very interested in women’s chests.” They settled.
71. There Is No Precedent for This Level of Ridiculous
I used to work for the Attorney General in my home jurisdiction. A man whose children had been taken away because of some very serious issues tried to get them back by claiming they were his intellectual property. He sent notices saying he had copyrighted the children and demanded their return.
Then he decided that his name and all of his children’s names were trademarks, so every time he received a court document that mentioned any of their names, he sent us an invoice for trillions of dollars for each use of his “trademarks.” It was easily the wildest case I ever worked on.
72. The Sun Is Always Setting Somewhere
Not a lawyer, but I was in traffic court when a cab driver was fighting a ticket for running a red light. He argued that the light was hard to see because the sun was rising right behind it. It was morning. He was driving west.
73. Worst Case Scenario
We had a couple who were both lieutenant colonels in the Air Force. They had one daughter who was 11. Both had graduate degrees and were generally intelligent people. The husband had an affair, the marriage fell apart, and the daughter, who was at that age when things with her mother were getting a little tense, said she wanted to stay with her dad when her parents split.
The mother completely lost it. First, she went to the local police and claimed the father had been hurting the daughter. They investigated, found no evidence, and dropped the case. Still furious, she then went to the Air Force Office of Special Investigations and made the same report.
The Air Force suspended the husband from duty and ran its own investigation, with the same result: no evidence of wrongdoing, and the case was dropped. Then the mother went to the next state over, where the husband was about to be transferred, and told the local police there the same story. They did their own investigation, got the same result, and dropped the case too.
During all of this, the daughter was interviewed over and over by psychologists, therapists, law enforcement, the Air Force, and probably others too. She was clearly traumatized by the whole experience. It also badly damaged her father’s career. He was basically shut out from any future promotion just because of the accusations.
When all of this got back to the judge, he was furious. He was a former Air Force JAG and still had connections, so he was in a position to make things happen. At one hearing, he told the ex-wife directly that she needed to stop immediately or he would hold her in contempt of court for the maximum time the law allowed.
He also said he would contact the DA and recommend charges, contact her Air Force superiors and push for the strongest reprimand possible, and do anything else within his authority. It was one of the most disturbing things I saw in my relatively short time in the courtroom.
74. Not Your Average Loophole
My uncle represented a man divorcing his wife after 15 years of marriage. It was a terrible breakup, and they split everything 50/50, including the land where their house stood. The wife then decided to build a new house directly behind the old one. There was a lot of land, probably about 200 yards between the two homes, but the backs of the houses faced each other.
After the house was built, my uncle got a call from his client asking whether a situation he had created was legal. Apparently, his ex-wife spent a lot of time in her backyard, so he saw her often. What he did was buy a female dog and give it the same name as his ex-wife. You can probably see where this is going.
Any time he called the dog back inside, he would yell, “Susan, get in here!” If the dog was peeing on the flowers, he would shout, “Susan, quit peeing on the flowers!” Or, “Susan, quit digging in the dirt!” The ex-wife called the authorities on him a few times, but there wasn’t much they could do because the dog really was registered under the name Susan, and it really was a female dog.
75. The Virtue of Honesty
I was involved in a pretty messy custody case. The other party was all over the place and had kept the child from my client for weeks. He was playing a lot of games and kept asking for continuances. I requested a substances test, which the judge ordered. But when the guy showed up, he stood in front of the toilet for literally two hours and claimed he couldn’t pee.
I was representing the plaintiff, so the burden was on me. I called several witnesses who testified about the defendant’s substance use. Then opposing counsel decided to call their client for direct examination and asked, “You don’t use crack or coke, right?” I fully expected the defendant to lie and say he was clean. Instead, after a long pause, he said, “Yes, I do both of those.”
My head nearly exploded. I didn’t ask a single question on cross because I didn’t want to muddy the waters. I won, and the child is doing great.
76. Munificent Motivator
Oh, I’ll never forget this one.
Client: “I want to leave $100,000 to my son, $100,000 to my daughter, and $10,000 to each of my ten nephews.”
Lawyer: “But sir, your estate is worth about $500. Where exactly are your heirs supposed to get that money?”
The client slammed his cane on the floor and shouted, “EARN IT, JUST LIKE I DID!”
He was not happy to learn that this is not how wills work.
77. A New Meaning To Plea Bargain
Several years ago, I was handling a civil trial involving personal injury. I was defending a woman who allegedly hit a bus monitor with her car. We had offered to concede liability and focus only on damages. In other words, the jury wouldn’t hear how the injury happened. We would simply agree that my client caused it, and the jury would decide how much money, if any, the plaintiff should receive.
We had evidence suggesting the plaintiff was greatly exaggerating her injuries. But the plaintiff’s attorney refused our offer, apparently thinking that if the jury heard the facts of the incident, they would want to award even more money to punish my client.
So we went to trial on liability. The plaintiff called exactly one witness: her own client, who testified that an older woman in a green car hit her.
Then they rested, and I moved to dismiss for failure to prove the case. There was absolutely no evidence linking my client to the incident—just testimony about an older woman in a green car. The plaintiff never even called my client to testify.
The attorney told the judge that the bus driver had written down my client’s license plate number and given it to the authorities. But they had never bothered to locate the bus driver.
Then the attorney asked if she could simply submit the report. I objected that it was hearsay. She actually said, “Please just let me put this in. I haven’t had work in a while, and a firm retained me to try this case. I really need to win.”
Naturally, I did not agree, and the judge dismissed the case. I felt a little sorry for her, but it was probably the worst case presentation I have ever seen.
I spoke to the jury afterward, and every one of them said they disliked the plaintiff, didn’t believe her testimony, and probably would have ruled for my side anyway.
Moral of the story: be prepared in court.
78. To Beyond The Grave
I once advised on a will in which the deceased had left substantial assets to people who were already dead by the time the will was read.
That alone is not especially unusual. The odd part was that these people had died long before the will was even written.
Apparently the lawyer asked him, “You do realize you’re leaving your money to dead people?” and even sent him to a doctor to have his mental capacity assessed.
The doctor gave him a clean bill of health and said he was fully compos mentis, so the will stood.
79. Don’t Be Rude
I was in court for a hearing. The judge was already in a bad mood and asked why we were even there for what seemed like pointless litigation. Without going into detail, the judge had a fair point.
The barrister had just started presenting our case, and I was taking notes on issues we needed to explore further, when suddenly I heard, “EXCUSE ME, WHY WERE YOU SO RUDE TO ME?”
Our client—who had specifically been told not to come—had shown up to court and was clearly furious that the judge had questioned the value of the case.
They went on scolding the judge for about three minutes. My co-counsel and I were first stunned, then desperately trying to get them to stop, before the judge finally adjourned the hearing.
It was remarkable to watch.
The case did not go well afterward, much to my client’s surprise and anger.
80. Pro Bono Mishaps
Someone I knew once had a pro bono case where she was defending a person charged with an offense. I don’t know what the charge was—it was confidential—but I do know the case against him was very weak and mostly circumstantial.
So she told him clearly to stay quiet and let her do all the talking during the trial. She made her argument and showed that the court had very little against her client. For once, it looked like a pro bono case might actually go her way.
After she finished, the judge thanked her and turned to her client. He asked whether the client had anything he wanted to add.
The client looked at her, then back at the judge. His eyes filled with tears, and he blurted out, “I’m so sorry, I’ll never do it again!”
She threw her notes—and just about everything else she was holding—at him.
Her client completely undermined her defense and made things far worse for himself.
81. Kiss And Tell
Here’s a clearer, more conversational rewrite with a very similar length and toned-down language:
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I worked as a paralegal while I was in college. We had this huge case involving a lot of people, and it had split off into several smaller side cases. In one of those, a man claimed our client had left him threatening voicemails, so he and his wife sued for loss of consortium. When I learned what that meant, I was stunned.
Loss of consortium, and yes, this is an actual legal claim, basically means something happened that interfered with a married couple’s intimate relationship, and they want to sue over it. The man said he was so shaken by the voicemails that he could no longer be intimate with his wife. When the deposition came around, I was sitting in the next room. It was a small office, though, so I could hear everything.
My boss started asking the wife how anyone was supposed to know it was our client’s fault they had stopped being intimate. Maybe she just wasn’t as attracted to him anymore. Maybe he wasn’t attracted to her. Maybe their relationship had already been struggling in that area, and so on. Her reaction was completely over the top. She started shouting, “I love intercourse!” while pounding her fists on the table.
Her lawyers tried to calm her down and told her to stop talking, but she kept yelling, “I love it! We used to do it two, three times a day! We’d get thrown out of hotels because of how loud we were!” And despite everyone in the room objecting—both her lawyers and ours—she went on to describe their private history in graphic detail, all of which was recorded in the deposition and filed with the court.
82. Judges Don’t Really Like The Thug Life
A young woman and a young man had a child together. The woman filed for divorce because the man was deeply invested in a reckless lifestyle. He had recently been arrested and charged with possession. The man did not take the breakup well. He hired a well-known local divorce attorney and got a temporary order saying she could not have overnight guests of the opposite gender.
The woman started seeing someone new, and the man was furious about it. He had his expensive lawyer request a hearing, accusing her of violating the court order. On top of that, he was asking for full custody of the children, attorney fees, and more. Things were turning messy fast, so the woman, on the recommendation of a mutual friend, hired me to handle the hearing.
I met with opposing counsel, and she immediately tried to intimidate me. Her demands were extreme. She said the mother should not only lose primary custody, but should have only supervised visitation and should also pay child support and attorney fees. She knew I was a very new attorney in town. She made it clear she was ready to fight it out in court.
I walked into the hearing with a copy of the man’s probation paperwork from his earlier case. He was careless and had never told his attorney about it, so she had no idea he had a record. She called him to the stand and had him explain all the nights my client’s new boyfriend had stayed over. The judge was very conservative and clearly unhappy.
But then my questions changed the whole hearing. I asked the ex-husband if he had a job. “No.” How did he make money? “Odd jobs here and there.” Oh? Your lawyer is pretty expensive. Do you sell illicit substances? “What?” Have you ever sold them to get by? “Uh, no.” That was when I introduced a copy of his guilty plea and probation sentence.
Now the judge was glaring at him. I leaned over to my client and whispered, “If you took a substances test today, be honest, would you pass?” She said yes. I then asked the man, “When was the last time you used?” His attorney objected, but the judge overruled it. At that point, I knew I had him, because this judge was known for ordering on-the-spot tests and had done it many times before.
The angry ex said, “It’s been years. I’m clean.” “So if you were tested today, you’d pass?” “Yes.” Opposing counsel then asked my client the same thing, and we agreed to testing. The judge had both of them tested. He tested positive. My client was clean. The judge denied his motion and asked me to submit new temporary orders requiring the man to maintain employment and begin paying child support.
But the best part came afterward. The icing on the cake was that opposing counsel actually called me and left a voicemail congratulating me on, as she put it, “handing me my first real courtroom loss in a long time.”
83. Status Update: You Lose
I was representing a plaintiff in a hit-and-run case. Even though I had spent hours preparing her the day before, she turned out to be an absolutely terrible witness in her own case. Just awful. She could not even identify the street she had been crossing when the car hit her. The real turning point came during cross-examination.
Defense counsel pulled out a photo of my client dressed up and ready for a night out, which had been posted on Facebook the day after the alleged accident. Thinking quickly, I objected, arguing that the timestamp only showed when it was posted, not when it was taken. So defense counsel handed the photo to my client and asked when it had been taken.
She confirmed that it was taken the day after the accident—meaning at a time when she was supposedly in severe pain.
84. Restraining Order Backfire
A wife filed for a restraining order because she wanted to stay in the house during the divorce. The husband had a strong job, earning around $200,000 a year. His employer found out about the restraining order and fired him. He worked in a highly specialized field, so the only job he could find near the house and close to his daughter paid about $50,000. That changed everything, and not in a good way.
The house went into foreclosure. Child support ended up being set at less than $500 a month. The wife had to get a job as a waitress.
85. A Shocking Turn of Events
The strangest and most embarrassing will reading I ever handled took place in a room packed with relatives. A man who had died fairly young left absolutely everything to his 26-year-old stepdaughter, including a very large amount of money and property. His two ex-wives, his children from his first marriage, and the rest of his extended family got nothing. The will specifically instructed that a DVD be played to explain why the stepdaughter was receiving it all.
Like everyone else in the room, I assumed it would be a video of the man explaining his reasoning and delivering one final insult to the family. What happened instead was completely unexpected. The DVD contained a hidden-camera recording of the man and his stepdaughter in bed together. It began right in the middle of the encounter, clearly edited that way for maximum shock, and it definitely worked.
It took me about 30 seconds to recover enough to turn it off. Without question, it was the most jaw-dropping moment of my career. Later, I learned that the man and his stepdaughter had reportedly been involved from the time she was a teenager until his death, when she was 26. According to secondhand accounts, which I cannot personally verify, the DVD included several clips from different points over the years.
At the end of the DVD, the man explained that the stepdaughter was getting everything because she had been, in his words, “the best partner of my life.” The worst part was that the will required me to give every family member a copy of the DVD. The copies had already been handed out before the video started, so everyone was sitting there holding their own copy while it played.
Epilogue: the family sued and lost, unbelievably. The stepdaughter kept everything.
86. Too Big to Know Better
As a corporate lawyer, one of the most absurd arguments I hear almost every month goes like this: a Fortune 500 company signs a terrible contract and is about to lose a huge amount of money because of the contract’s plain wording. So the company argues unconscionability—specifically, that it wasn’t sophisticated enough to understand what it was signing, and that no reasonable person would ever have agreed to the terms being challenged.
So, in short, multi-billion-dollar companies claiming they can’t read contracts.
87. Self-Sabotage
This one will probably always be my favorite. I was handling a boundary dispute, basically a fight over a few inches of land. The person on the other side was a lawyer, and a deeply unpleasant one at that. He was representing himself and clearly thought he was the smartest person in the room.
Part of his case centered on wheelie bins. He argued that before the boundary changed, there had not been enough room to store a full-size bin beside the house. The fact that there was room now, he said, proved the boundary must have moved. That was basically the whole argument. It was incredibly weak, but he was completely committed to it.
During the trial, he tried to pull a surprise move by suddenly producing an old aerial photo, supposedly to show that the boundary at the front of the property had moved too.
Normally, you have to disclose something like that ahead of time. You can’t just hold onto relevant evidence and then dramatically reveal it at trial. But this went very badly for him. While he was making his arguments, I took a closer look at the photo and realized it clearly showed a wheelie bin in exactly the spot where, according to his case, one could not possibly have been.
I told the judge we were happy to have the photo admitted after all, got the other side to confirm the date it was taken, and then pointed out that he had just destroyed his own case. It could not have happened to a more fitting person.
88. Her Own Worst Neighbor
I had a short consultation once involving a possible personal injury claim. An elderly woman slipped and fell on an icy driveway that had not been salted or maintained, and she wanted to sue for damages. After hearing the full story, it turned out she had fallen on her own driveway—the one she herself had not salted or maintained. She wanted to sue herself.
89. Good Call
This never actually went to court. I once asked my divorce lawyer what the worst thing a client had ever wanted him to argue was. I expected something trivial, like a fight over a kitchen gadget.
Instead, he told me about a client: a professor in his seventies who was divorcing his wife, also a professor in her seventies. They were both Jewish. His wife had a tattoo on her arm—a number given to her by the Nazis when she was placed in a concentration camp as a child during World War II.
The husband had been born in the United States and was not German. At the time, the German government was settling claims with survivors, and she was due to receive a six-figure sum. The husband wanted his lawyer to argue that he should get half of that settlement money.
The lawyer told him there was a special place in the afterlife for attorneys who make arguments like that, and he had no intention of ending up there.
90. Psycho: The True Story
In October 2020, my husband and I were renting one side of a duplex owned by my father-in-law. The other side was owned by a different family—an adult daughter caring for her elderly mother. We brought our son home from the NICU in August, and by late September, the caregiver next door started banging on the shared wall whenever she heard him cry.
Over the next two months, the banging got worse. Then it took a frightening turn. The younger neighbor bought a megaphone and used it to shout through the wall, threatening to “rip us apart.” She called us child predators and yelled threats until three or four in the morning. We called the authorities multiple times, but nothing was done.
One officer told us, “Threats don’t matter unless you actually carry them out.” No one had seen the elderly mother in months, but requests for wellness checks were dismissed. I was basically told that, as renters, there was nothing we could do. Someone even suggested the neighbor’s behavior was understandable because a crying baby was probably very irritating.
Eventually, we moved in with my grandmother because we no longer felt safe. By that point, the neighbor had punched a hole about the size of a softball through the shared wall so she could scream at us—and sometimes just stand there and stare. But what happened next was almost impossible to believe. The smell coming through that hole was terrible. Looking back, that should have told us something was very wrong.
Our security cameras also recorded her going to my son’s nursery window around 2 a.m. almost every night, just standing there holding her cat. It was not until the end of January that authorities were finally able to enter her property. When they did, they found that the elderly mother had been dead since at least June, and the daughter had left her body, dressed in her Sunday clothes, in a deadbolted bedroom.
The news report said the mother had died of natural causes. The daughter was taken to an inpatient psychiatric facility.
91. Doing His Duty
This woman spent nearly the whole case criticizing the man she said was the father of her baby. She had people pointing out supposed genetic similarities between the child and the “father,” and kept insisting the whole thing was absurd because she hadn’t been with anyone else in years. Eventually, the judge turned to the man and asked whether he had anything to say for himself, since he had been standing there quietly while his ex-girlfriend went after him the entire time.
He gestured that he had a folder of documents. The bailiff brought it to the judge, who reviewed it and then quickly dismissed the case in the man’s favor. It turned out he had been actively deployed with the Armed Forces for the past four years and wasn’t even in the country when the baby was conceived.
92. Jesus Walks
I once had a potential client come in and say he wanted to sue his uncle for murder. Leaving aside the fact that you can’t sue someone for “murder,” I asked, “Who did your uncle murder?” He answered, “Me.” I declined the case.
93. Animal Instinct
A woman called and said she had a product liability case involving animal crackers she gave her daughter. At first, I assumed it would be about food poisoning, so I kept listening. I regretted that pretty quickly. She explained that when she looked at the crackers, it seemed like the monkey was holding its crotch.
It wasn’t. It was a banana. Still, she said she felt deeply embarrassed and upset. According to her, she told all of her co-workers, and they were shocked and uncomfortable. I wanted to tell her she was overreacting and that they were probably just confused, but I kept that to myself.
94. Latte And Order
A family friend of mine is a lawyer. Someone once came to her wanting to sue Starbucks because a person had spilled a latte on the sidewalk, and she slipped on it and hit her head. She argued that Starbucks was responsible because none of it would have happened if they hadn’t put “extra slippery whipped cream” in the drink. My friend passed on the case.
95. A Good Foundation
I do a lot of insurance work and handle all kinds of cases, big and small. One smaller case involved about $2,600 in damage after a contractor drove into a retaining wall at a woman’s house. He refused to repair it, and after around eight months, the homeowner allowed her insurance company—my client—to fix it and send the bill to the contractor.
Not surprisingly, the contractor refused to pay. There was a lot of back-and-forth between my client and the contractor’s insurance company, which offered less than $500 on a $2,600 bill. We ended up going to trial. I brought our claims adjuster and the homeowner. The defense attorney brought the contractor and an adjuster from the contractor’s insurance company.
Everything went smoothly when questioning the homeowner, who was a kind, middle-aged woman. Like most people, she didn’t know much about the details of masonry work. Then my claims adjuster testified. He explained that we paid $2,600 to have the wall repaired, though he also admitted he wasn’t a masonry expert. He did, however, talk about how masonry estimates are prepared.
I finished presenting my side. Then the contractor took the stand. They asked him about what happened with the retaining wall, and then he testified that he “knew for a fact” the $2,600 invoice included overhead and profit. He even accused my client of “running a scam.” The judge struck that statement. I looked down at the repair estimate and could hardly hide my smile.
In bold print, it said: “This amount does not include overhead or profit.” I checked the invoice. It was the exact same amount as the estimate. This man was clearly not telling the truth, and now I had the chance to show it.
During cross-examination, I handed the contractor the invoice. “Sir, this is a $2,600 invoice for the repair, correct?” “Yes.” Then I showed him the estimate. “Sir, this is a $2,600 estimate for the same repair, correct?” “Yes.” “They are the same amount, correct?” “Yes.” “Does the estimate say it does not include overhead or profit?” “Uh...” “Does it?” “Yes.” “Didn’t you just testify that you knew for a fact the estimate included overhead?” “I don’t know.” “What don’t you know?”
At that point, the contractor got angry and slammed his hand on the stand. “It doesn’t include overhead and profit, does it?” “I guess not.” “But you said it did, right?” Then I ended my questions. But I wasn’t finished yet.
Next, the defense attorney called the adjuster from the contractor’s insurance company. He testified about what he believed the repair should have cost—around $500. I cross-examined him.
“How did you come up with that estimate?” “I entered numbers into a computer program.” “How did you know what numbers to enter?” “Uh...” “Are you a contractor?” “No.” “Are you an expert in masonry?” “No.” “Have you ever worked in construction?” “No.” “And the computer program gives you an estimate based on what you enter?” “Yes.” “So you can put in whatever numbers you choose?” “Yes.” “And it creates an estimate based on those numbers?” “Yes.” “But you don’t actually know anything about masonry?” “No.”
So the adjuster had basically just admitted that he guessed. The defense rested, and the judge took the case under advisement. To sum it up: the contractor was caught lying, and his insurance adjuster admitted his estimate had no real expertise behind it.
In the end, we were awarded $1,000. That was less than half of what we asked for, but still double what the defense argued the case was worth. I counted that as a win.
Unsplash
96. Not A Lucky Divorce
A woman won $1.3 million through a lottery pool and filed for divorce just 11 days later. She never told her husband about the winnings, and she also failed to disclose them during the divorce. She probably would have gotten away with it too, if not for a letter that showed up at their old marital home more than two years after the divorce was finalized…
The letter was an offer to cash out her lottery annuity in exchange for a lump-sum payment. Her ex-husband quickly hired a lawyer, and the family court ended up awarding him 100% of the lottery proceeds.
97. I Don’t Think That Word Means What You Think It Means
This one was wild. A few weeks ago, my co-worker’s girlfriend filed for divorce. Yes, girlfriend. They were never married, and common-law marriage doesn’t exist in my state. They lived together for five years. She has her own job. Her name isn’t on the mortgage. She moved out a few months ago. There are no kids involved, and they were never even engaged.
In this so-called “divorce,” she wants him to move out of his own house so she can move back in. She also wants him to pay her $2,800 a month for no clear reason. I sent him to my divorce attorney, who will probably end up representing him. She’s completely unreasonable. She already tried to get a restraining order against him, but it was thrown out.
98. Consider The Source
My dad is a physician and sometimes serves as an expert witness in malpractice cases. In one case I’ll never forget, a family was suing a doctor over something pretty minor, and my dad was testifying for the defense. The family’s lawyer was cross-examining him and brought up a chapter from a medical textbook, then asked my dad to read a highlighted paragraph.
My dad read it, and the lawyer said something like, “So what you just read means ‘blah blah medical thing.’” My dad calmly answered, “No, that’s not what it means.” The lawyer pushed back and said, “But if you read xyz, the author clearly means ‘blah blah medical thing.’” Again, my dad said, “No, that’s really not what the author meant.”
The lawyer had no idea where this was going. He asked, “How do you know that’s not what the author meant?” My dad replied, “Because I wrote it.” The judge basically put his head in his hands while the lawyer just stood there staring at the author’s name on the chapter. It was probably the best moment of my dad’s professional life. And yes, the ruling went in the defendant’s favor.
99. Miracle Babies
My ex-wife is suing me for child support, but I physically can’t father children. I lost that ability when I was 14 because of a serious health issue. I married a woman who originally said she was asexual, but later she told me she was pregnant with twins by a man she had been seeing. We divorced before the children were born. Now it’s four years later.
Then I got a letter in the mail saying I’m being sued for child support. The children are absolutely not mine, and we were already divorced before they were even born. I’m in a terrible situation. My health is bad, and my finances are extremely limited. I’m barely getting by as it is.
100. Get OUT
I think my boyfriend may have been secretly drugging me for some time and then making me doubt my own memory. I know this is hard to explain, but I’ve been having memory gaps that I kept blaming on being tired, overworked, or something else. I was going to ask my boyfriend about it, since he’s a doctor, but then I started noticing something really disturbing.
This seems to happen when I go out with him. I know it sounds unbelievable, but I’ve woken up several times with dried residue on my chest and no memory of the night before. I’m convinced it’s him. The first time it happened, we had been drinking, so I assumed I had just had too much. But later it happened again on nights when I know we had not been drinking.
I decided I wanted to break up with him over this, but then somehow found myself out on a date with him a few days later. I hadn’t actually had the breakup conversation yet, but I was planning to the next time I saw him. I remember being at the restaurant, but nothing before that. Both my car and his were in the parking lot, which confused me. When he asked me to come back to his place, I went along with it.
After spending three days there, I started remembering everything again, so I began to trust him a little more. I was about to ask him about the memory problems when he suddenly pointed to red bumps on my thigh and said I should treat those sores. I had completely forgotten they were there. They looked like small needle marks that had become irritated. I got so scared by the fact that he brought them up that I left.
The next day he came over to “check on me,” and I remember waking up in bed again with no memory of what had happened. Then today he met me for lunch, saying we had made plans. I never agreed to meet him, and at this point I absolutely would not want to. He does this constantly, saying we agreed to things I have no memory of. I’m exhausted by it and want him held accountable.
This is starting to affect my job too. I get paranoid when a boss walks into a room after making eye contact with me, because I think I’m about to be fired. My friends say I’ve been acting strangely and not like myself. I’ve also started losing sleep, and when I do sleep, I sometimes sleepwalk. Is there any way to get blood work done to find out what kind of substance he may be giving me?
101. When It Hits The Fan
I was a young prosecutor at my local district attorney’s office, fresh out of law school. We had a specially set trial on a case that had already been continued far too many times. By the week before, it was obvious this one was finally going forward. I was sitting at the State’s table, ready to begin, when defense counsel walked in and told me he planned to ask for yet another continuance.
I’m pretty sure I laughed because I assumed there was no chance the judge would allow it. I was very, very wrong. The judge came in already irritated that he had to hear another continuance request. Around the same time, I noticed a bad smell in the courtroom but couldn’t figure out where it was coming from. The judge asked defense counsel why he needed the delay, and the attorney opened his briefcase.
I will never forget what came out of it: a Ziploc bag containing soiled underwear. He explained that he had suffered an accident that morning while in court. He was an older attorney and had been taking stool softeners. The continuance was granted, and the courtroom was actually closed for the rest of the day so maintenance could clean and shampoo the seat where he had been sitting.
I never found out what happened with that case. I didn’t end up trying it; maybe another prosecutor did. But it remains one of the most memorable “I rest my case” moments I’ve ever seen a lawyer pull off.
102. A Fatal Mistake
I once represented a nurse who had given a fatal injection to a baby. It was a deeply upsetting case, but I was able to get her cleared of negligence charges. This happened many years ago, and it has stayed with me ever since. For anyone interested, here’s the full story.
It happened after hours at a small rural hospital that was short-staffed and lacked proper equipment. In the pediatric ward, a baby was critically ill with gastroenteritis and had not improved after weeks of treatment. Despite every effort, the baby kept losing weight. That night, there was no doctor in the pediatric ward—or anywhere else in the hospital.
When the lab called in the baby’s blood test results, the nurse on duty was told the baby might not survive much longer without urgent treatment. She called the doctor, who was at home. He had already worked long hours that day and was only supposed to be available by phone.
The doctor instructed that the baby should be given an ampoule of potassium chloride, and the nurse wrote the order down. But the doctor made a fatal mistake: he did not specify that it was meant to be given orally. Because he had said that a nursing sister needed to administer it, the nurse assumed it was intended as an injection, since she was not qualified to give injections herself, while the nursing sister was.
The nurse called the sister from the maternity ward and asked her to come immediately. She explained how urgent the situation was. Although the sister was very busy, she came to the pediatric ward and administered the injection. The baby died almost immediately from cardiac arrest. The partners at my firm did not want to take the case because they believed it was impossible to win.
But under our law, negligence has a very specific meaning. I defended the nursing sister by arguing that she had done her best with the information and resources available to her, in a crisis where she had been told the baby might die very soon without treatment. She was a deeply committed professional, and what happened had completely devastated her.
She had reached the point where she wanted to leave nursing altogether. I hope she eventually decided not to. There was one small good outcome from the tragedy, though. I mentioned to a member of the local Rotary Club that this hospital desperately needed telemedicine equipment, knowing the club supported projects like that.
Not long afterward, the club was able to donate equipment to the hospital. Years later, I even happened to see that doctor again, and the doctor was extremely grateful for the donation. It truly changed conditions there and made it much less likely that something like this would ever happen again.
Pexels
103. X-Ray Vision
In one case, a client suffered radiation burns from an X-ray machine. During discovery, we received a huge volume of records from the defendant. Buried in all that paperwork was one internal memo that broke the case wide open. It described a serious defect with the machines and included the line: “This is an issue we can’t ignore. Unfortunately, it’s not in the budget.”
At trial, we told the jury, “Show them that next time, it needs to be in the budget.” The jury did exactly that, returning one of the largest verdicts California had seen at the time.
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