Court Officials Share The Weirdest Cases They Have Ever Seen
Image by Carrie Z from Pixabay

Never underestimate how insane some people are, even under the pretenses of civility. A courtroom is no place for the worst secrets you've had to be revealed, but unfortunately that's where a lot of them come out. It's a courtroom official's job, be they a judge or attorney or clerk, to handle them with the utmost care and with a keen eye.

Sometimes, however, they're just too weird not to talk about on the internet.

Reddit user, u/ThatOneDoveSlayer, wanted to know about:

[NSFW] Judges of Reddit, what are some of the weirdest cases you've seen?

Never Underestimate People's Pettiness

I was a mediator in small claims court in Queens NY during law school. Mediators attempt to help the parties reach a settlement. A woman brought a claim against a shoe store. According to her, there was a display with shoes for $20. When she got to the register with two pairs of shoes, they charged her $25 per pair.

She complained and told the counter person that they were on sale for $20. She brought the counter person to the display and, according to the woman, they had switched the sign so that it now said $25. She paid the $50 and then sued for the $10 extra that she had to pay. The cost for filing the claim was $15.

After she told me her story I met with the two lower level employees that the shoe store had sent to the court. They of course denied changing the sign, but I told them they can settle for $10 and leave immediately or they would have to wait for a judge to decide the case. They happily paid the $10. The woman lost five dollars in the transaction.


What A Way To Celebrate?

...Had my first argument before the Second Circuit, so obviously fairly nervous. The case before me had a very generic name, think "Smith vs. Generic Insurance Corp." Figured it was going to be dull...

But instead, it turned out that the issue was that Mrs. Smith, a widow, had her husband's life insurance payment denied.

Why? Husband was an engineer of some sort and had constructed a device to... pleasure himself. He plugged said device into a wall socket on to "enjoy" on Easter Sunday, while his family was out, but unfortunately was electrocuted and died. (And presumably was found by his poor family on Easter, pantsless and plugged into the wall).

The insurer tried to deny benefits based on an exclusion for "intentional self-harm." Cue a solid 20 minutes of the insurer's lawyer being grilled by very staid and conservative judges as to whether the poor guy actually intended to harm himself, or, as one judge put it very mildly... "it seems the deceased intended... well... the opposite." And the insurer lawyer struggling to articulate why self-harm and sexual pleasure are not always mutually exclusive.

From the questions, it seemed like the widow was likely to win. But man was that awkward for everyone involved.


You Know You're Kind Of Exposing Yourself, Right?

Plaintiff filed suit in small claims court because the Defendant did not perform the sexual acts that Plaintiff paid the Defendant for.

It ended up settling in mediation which was good for the Plaintiff because it would have had to be reported for potential criminal charges if it made to court.


Everything Has A Price

My dad is a judge and had a case that revolved around Bull Sperm. Basically someone leased a bull and wasn't supposed to breed it and they bred it anyway and the owner sued for the price of the sperm.


Hammer Time

My father was a circuit court judge for a number of years. He used to tell me all kinds of stories, but my favorite was from a divorce dispute. The two sons of the husband and wife were messing around and they made a hole in the wall. The father was upset so he grabbed a hammer and punched a bunch of holes into the wall to prove to the boys how bad the holes look.

I don't remember the exact number, but it was around 90. When the attorney for the wife asked him if it was a good idea the husband said " hindsight...I guess maybe not." My father said that's the only time that he's ever almost burst out laughing in court.


Not His First Rodeo

Not a judge; brother-in-law was clerk of the court for most of a decade.

Dude comes in with an indecent exposure charge; he was walking around the local Target in super shorty shorts, and his lil' Shortie was longer than the shorts. Okay, this is supposedly fairly straightforward- slap on the wrist and get told to buy longer shorts.

Except it turns out this isn't this guy's first rodeo. In fact, it's his TWENTY-FIFTH rodeo. Dude is an exhibitionist, and this was his MO. He was already banned from all retail establishments in half the counties in the state, and a handful of counties in the neighboring states. At this point he'd had so many convictions that he was looking at 25 to life for f*ckin' indecent exposure.

Oddly enough, there was another indecent exposure case involving the other local Target a week later. Dude was standing up in the open bed of his pickup at 2am in the Target parking lot.


Judge Burn!

I once attended oral arguments for US Court of Appeals for the Second Circuit. It's pretty much the big time.

I watched a lawyer argue that his client received what's known as "ineffective assistance of counsel" at the trial from which she was appealing.

The attorney however was not doing a very good job during oral arguments. So, at one point one of the judges on the panel leans forward and asks him "counselor, are you currently providing ineffective assistance of counsel?"



I'm a lawyer considering whether to someday be a judge. The Dildo Bomber was the oddest case I've worked on so far. Boyfriend gets dumped in spring, stalks ex-girlfriend for 9 months. He's known to have an obsessive interest in bombs and explosives.

In December, he delivers a package to ex-girlfriend. There's no return address, but it says "MERRY XMAS B*TCH", so it doesn't take a rocket scientist to figure out who sent it. Ex calls the cops, who call the bomb squad, who open the package. Inside is a large vibrator that's been hollowed out and filled with explosives. He apparently assumed that she would eagerly use it and blow herself up. This is how you know that men and women think differently...


Wait For It...

Worked in LE for a long while. Escorted an inmate to court for his dismemberment and murder charges trial. He chose to represent himself. Context: was infatuated with Charles Manson and cults. Started one that preyed on mentally unstable/ handicap women and killed them if they tried to leave. This poor girl with autism wanted to go home. He killed her with his followers help, chopped her up, and burned the pieces in a dumpster.

His opening statement was something along the lines of "Ladies and gentlemen of the court I just want to clarify that things being inserted into my butt are going to come up in this trial. I'm not gay. I just liked it." The judge said what the f**k, but caught himself before dropping the f-bomb. Everyone in the courtroom laughed at him. It was thrown out and he went for mental health screenings.

I don't miss LE work... at all. I did accrue a sh!t load of stories though.


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