Lawyers Reveal Their Most Cringeworthy Cases

Frivolous lawsuits. Greed. Stupidity. Suing people is the American way, and people conjure up all sorts of reasons for trying to screw someone over in court. Lawyers know what's up, though, and the things people try to sue for are truly bonkers.

ThyDillyDilly asked lawyers of Reddit: What's the most cringey case you've had?

Submissions have been edited for clarity, context, and profanity.

10. Well that's definitely not how it works.

I was defending, the plaintiff's case was dismissed for failure to state a case. Basically, under the law, they weren't entitled to any compensation. They appealed this decision and lost. They had a month to appeal. 3 months passed, and nothing. Then we get a notice that they're appealing. Half of their appeal was their attorney begging the court to consider the appeal because of how difficult his last 3 months had been. The difficulty? He moved across town 2 months prior and had been renovating his new house.

Maybe not very cringy to the average person, but the audacity of blaming a 3 month delay on moving was something else.


That takes a lot of chutzpah, mixed with an equal amount of pants-on-head stupidity.

His filing is probably going to be the first exhibit in the forthcoming malpractice suit, or, at the very least, will not play well in the bar discipline proceeding.


9. Food stamps... for a dog?

We interviewed a middle aged man who was poor and received food stamp assistance for himself. He had an emotional support dog, some kind of toy breed who was untrained and most likely just his pet. According to him, the dog could only eat expensive organic whole foods and could not eat ordinary dog food. He applied for what basically amounts to food stamp assistance for his dog.

The state granted the food stamp assistance for the dog. He came to us OUTRAGED because the amount of food stamp money he got for the dog did not allow him to buy the organic whole foods that the dog required. He wanted to appeal the food stamp decision and get even more money. We turned the case down. This resulted in claims of disability discrimination against everyone in the office who interacted with him.


This is why some people are against welfare programs. Most people don't mind helping actual poor people but I think we'd all agree we don't want our tax dollars wasted on gourmet food for someone's pet dog that they shouldn't even have because they can't afford it.


8. Can't do that.

Guy wanted to declare bankruptcy for gambling debts. They weren't even big debts. He just felt like they were too annoying in trying to collect on the debt that he wanted to stiff them by going through bankruptcy.


I declare bankruptcy!!!


That's not how it's done Michael.


I didn't say it, I declared it.


7. Yeah, creepy.

I rep. mom of daughter. Mom's boyfriend did a bunch of grooming behavior- including buying the daughter a lipstick adult toy and lube.

The mother completely and utterly "stood by her man"- and didn't care if it cost her custody of her daughter. Social services intervened- child was removed and placed into custody of bio father.

She retained me when bio father filed to terminate child support and have his own child support established.

The woman was in her late forties and wore pony tails on each side or her head and/or braids on each side of her head and had them decorated like little girls have. she also wore, almost constantly, what appeared to be a "Catholic school girl" outfit- tartan skirt, white shirt (low cut) and vest. It was if she was trying to look like a girl. I found her and her pedo boyfriend completely cringey.


6. This is why there are warning labels.

The dead penis consult. Years ago I did PI work. Older man came in and wanted to sue because he took off brand Viagra. You know the big warning about if the effect lasts for more than 4 hours go see a doc? Yeah. He did too....but he ignored it due to embarrassment. For 3 days. By the time he went in....blood had pooled, thickened, and completely destroyed his penis.

They open it up....remove what needs to be removed...tell him that was his last erection of his life. He is understandably bitter, but not much I could do since he admitted to ignoring the warning. That's when he stood up. In my office. Dropped trou with no warning and yelled that he should be paid for having to deal with his new dead situation. I asked him to pack up his situation and leave. Then I had a whiskey and resolved never to ignore any medication warning ever again.


5. Seems like a waste of money but okay.

Oh, there are so many cringey cases out there.

Mom and Dad are immigrants who are self-made rich ($100+ million rich). They have four adult children. Child 1 is a well respected physician. Child 2 is a college professor and successful author. Child 4 is a stay at home mom and socialite (her husband is a CEO in Silicon Valley). Child 3 is a scam artist, but even though child 3 is mom's favorite, she recognizes him for who he is. The whole family live in California.

Mom and Dad have long standing valid wills and trusts. About 15 years before, they paid a lot of money for bullet proof estate planning. Part of this was to ensure that Child 3 never had access to their money, he received a modest stipend (I think it was $5k/month for life, indexed to inflation), and that Child 3's kids (their grandkids) would be taken care of.

Dad dies, and mom has early stage dementia. Less than 48 hours after dad dies, Child 3 (representing himself) sues Children 1, 2 and 4 in another state where none of them live because he didn't like the fact that 15 years earlier mom and dad wrote him out of the will, and that dad hung on long enough for his kids to graduate from college (never mind that Mom and Dad paid for all 14 grandkids college educations), so he doesn't have access to his kids trust funds.

My firm's Senior Partner and Child 1 were fraternity brothers in college, and we happen to practice in the state where Child 3 brought his suit. I'm successful in getting the case dismissed for a lack of jurisdiction.

About 18 months later, Child 3 then finds out that Children 1, 2 and 4 are limited partners in a real estate development in my state. He sues them for their part of the real estate development, because they obviously invested Mom and Dad's money that he was entitled to. We're hired again, and successfully dismiss that case.

Three years go by (its now about 6 years from when dad died) and we find out that Mom has died. Child 3 sues us, as well as Children 1, 2 and 4, for medical malpractice (only child 1 is a physician) in yet another state. His reasoning? Because we had his cases dismissed, and mom died, then the fact that he lost his cases caused her to die. The fact that she was in her mid-80s and suffering from dementia couldn't possibly have anything to do with that.

My wife's best friend is an attorney in the same city where the case against us was filed. I pro hac vice in (temporary admission for a single case), and get this case dismissed.

The best part? All told, we racked up well over $200K in fees and expenses from all of this frivolous litigation. He's been ordered to pay us all of our fees, plus interest from the date of the beginning of case 1. With interest, its over $600K. We've garnished his stipend, so we're getting the $5K/month (which I now think is about $7K). It barely covers his interest. He's going to be paying us for the rest of his life, and we have a nice, guaranteed revenue stream.


4. Case closed?

A woman wanted to charge her ex for stealing her indoor/outdoor cat. The cat had been gone for two days. When it returned, it smelled like cigarette smoke. Her ex was a smoker, so she thought this was plenty of evidence against him.


When your cat has more fun on the weekends than you do...


3. I want to not pay taxes.

I defend corporations that fail to pay taxes.

A company failed to pay millions in excise taxes. They blamed it on another newer company that came in as competition to their monopoly on a very narrow niche industry within a broader industry. The pres of this corp sues the new company for hurting his business. I told him it wouldn't work and wouldn't find a lawyer to do it. He HAND WROTE his lawsuit and it was thrown out because it was frivolous.

As for my case, I saved him just over a million dollars with the IRS in Trust Fund Assessments. He is now on his third attempt to sue me for not saving him more money. The previous 2 attempts failed because 1: I have an arbitration clause, 2: His company is now defunct, and 3: I performed our contract to the letter. He hand wrote those lawsuits too. He is essentially harassing me with lawsuits because he has nothing better to do now. I will smash him like a bug in court again and round and round we go.


Is there a way to counter-sue him for frivolous lawsuits, and would it be worth your time?


Not worth my time. IRS took his major assets after he fired me and didn't maintain the terms of his agreement with them. It's honestly a free vacation every time he does it because my firm pays me to travel to a nice place (where he sues me) and I get to bring my wife with me. It's fine with me honestly. This guy is next level crazy so I really don't have to do much in court. I show my side of the story in the Statement of Professional Services Rendered, the Retainer Account paperwork and the Service Agreement. Same Judge has thrown it out twice before so it will happen again.


2. Okay then.

Man in his 50s is suing his female coworker about 30 years his junior. Woman just got married but the man had a crush on her.

He broke down and kept crying, confessing to stalking and sending her risque letters and maybe even breaking into her place.

His lawyer has to work hard not to get him put in prison.


1. Pics or it didn't happen.

My former boss wanted to take a botched penile implant case, but we convinced him not to because of the costs of litigation. The photos, my god, the photos.


Huh, I'm a 33 year old male who had never heard of a penile implant before this.

Thanks, I hate it.


What...what did it look like?

My morbid curiosity always gets the better of me.


Probably what it would look like if you tried to open a can of beans with your erection and didn't stop until you succeeded.


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