25 Unusual Legal Battles That Kept Lawyers Up At Night

Being a lawyer means encountering some of the most bizarre situations people can create. Representing someone in court gives lawyers access to all kinds of information that would otherwise stay hidden.

#1 One of my close friends is an environmental lawyer primarily defending individual landowners in corporate cases where discharge or pollution has occurred, or where water rights are in contention.

Image source: SweaterZach, Meir Roth / pexels (not the actual photo)

A couple years back, there was a case where a well-known manufacturer of latex paints was found to be poisoning a local wetland (a big f*****g deal in my state) with runoff, and the state authority in charge of wetlands preservation took them to court. In a grandstanding effort to demonstrate to the judge that the chemical being discharged near the water could not possibly be toxic to the wildlife, a rep for the company brought a powdered form of the chemical in and mixed it with a glass of water there and then, intending to drink it dramatically in front of the court.

The glass (actually plastic, but still) *melted right there on the table*.

The case was settled out of court the same day.

#2 There were cases in the UK during the Falklands war in the 80s where the government claimed bullet wounds and lost limbs due to minefields were “incidental” injuries and not related to the fighting.

Image source: WimbleWimble, Lukas / pexels (not the actual photo)

Like people just randomly generate holes in their chests and limbs fly off during birthday parties etc.

The government’s own records showed they were “buying time” in order that the claimants would hopefully die of their injuries and the cases could be shut down.

#3 TL;DR: lady wanted to show me her vagina, it just happened to not be attached to her body.

Image source: Tokra_Kree, ALINA MATVEYCHEVA / pexels (not the actual photo)

I already told one shocking story in this thread, but I got another that is a different kind of shocking.

I was pretty new to the practice and was meeting with a lot of clients. The firm I worked for had a lot of walk-ins and I was processing the potential clients.

I called in the next person and a mid-30s women walked in carrying a red and white cooler. She pops in down on my desk and the spends about 5 mins trying to sit down in the chair. My first thought was “must be some kind of personal injury.”

First words out of her mouth after she sits, “I need to sue my doctor because my vagina just fell out.”

My eyes immediately lock onto the cooler.

“Is…that?”

“Yes. I brought in with my just in case you needed to see it. Do you want to see it?” She begins to open the cooler.

Not gonna lie..I was curious but I stopped her and convinced her that a hospital was her best option at the moment.

Turns out she had vaginal reconstruction and the mesh came out in one big blob. Now, this is not my area of expertise. I am a corporate attorney. So I sent her to someone with more expensive.

Edit: meant experience not expensive but both are true so I’ll let it stand.

#4 Not a lawyer but my Aunt was.

Image source: ScubaNoname643, Tim Eiden / pexels (not the actual photo)

She was the state prosecutor for a case where a guy had gotten into an argument with another guy at a recreational baseball game.

After the game was over one guy left and went home. The other guy stayed at the baseball field with his son.

About like 30min to an hour later they are still at the baseball field and the other guy is back. He has a baseball bat and walks straight towards the dad at the pitching mound and starts hitting him over the head with the bat until hes unrecognizable. Kid frozen in terror while this guy murders his dad. He then walk over to the kid and does the same thing to him.

My Aunt was amazing at her job and got the guy sentenced to life in prison.

She lost her battle to cancer a few months ago. I loved listening to her stories. She was the best Aunt a guy could ask for.

#5 I’m an attorney, but the case that stuck with me most was one I sat in on during undergrad. I was a criminal justice major and frequently had to go watch trials for class assignments. I was in the military at the time, so I had to cram these hours in randomly — if we had a light day, or I could take a long lunch, I would go to the closest courthouse and check what was available.

Image source: kithien, cottonbro studio / pexels (not the actual photo)

One day, I went down to the federal courthouse in Baltimore and checked the list: one criminal case, nothing else going. I head upstairs and quietly walk in. Despite that, clearly, everyone checks me out, which is odd — usually, no one pays attention to the gallery. At the first break, a guy comes over and asks me who I am and why I’m there; he’s Office of Special Investigations (OSI) with the Air Force, so I show him my ID and explain I have to watch criminal trials. He gives me a weird look but doesn’t push. As I’m sitting there, I slowly realize I SHOULD NOT BE HERE. An Air Force couple has a son, and gets divorced. She takes her son with her to her duty station in Japan and remarries a civilian employee there. Dad is deployed, then moves station, and keeps bugging her about when he can see the son; at some point, she just stops responding. A few months later, after Dad has filed a report with her command, requesting they make her communicate with him, Dad gets a call from an OSI agent who he knows, asking him for his son’s full name and date of birth. Dad gives it to him, and the agent says, ‘Look. I didn’t tell you this, but you need to call OSI on her base.’ Mom had gone to the field, and her 8-year-old son had been bugging the stepdad while he was gaming. Stepdad got pissed off and beat the kid with the first thing to hand — a piece of banister from the stair he was working in. Mom came back from the field two days later and found the son unconscious, still on the floor. Because the stepdad’s last home of record was in Maryland, he was tried in federal court in Baltimore. I sat through the ER doc who treated the son, who talked about seeing the internal crush injuries, and the coroner who talked about how hard you would have to hit an 8-year-old on the front to cause bruising on his back. I also sat through the dad talking about finding out his son was gone. After that day, I always went to misdemeanor court for my hours.

#6 I’m not a lawyer but I worked in a foreclosure mediation/diversion court as a counselor.

Image source: BureaucraticHotboi, Kelly / pexels (not the actual photo)

Usually it was people with bad luck, unemployment or addiction that lead them there. Heavy stuff but became run of the mill.

One guy I will never f*****g forget. He comes in and at first it looks like a standard unemployment deal. There are programs with mortgage companies to deal with. He was a dock worker, made pretty good money, but hadn’t worked for 6 months and was about to lose the house. I ask for his story and he tells me it all started 20 years ago. His older son was in the army in Korea at a base on deployment and his younger son was at a high school party in their town. Apparently he gets into it with another kid over a girl, and the kid grabs a barbecue fork and stabs the son in the neck. His youngest bleeds out before an ambulance arrives. The older son is devastated because he wasn’t there to protect his brother.

The father and mother end up divorcing over the grief. But older son returns, makes a life. Has a couple young kids and it all seems good. But six months prior he just walks into his garage and shoots himself in the head. Leaves a note that he can’t live with not having been there for his baby brother even after all these years.

So my client goes into a depressive state, stops working, stops paying bills. Just can’t deal with the grief and destruction of his family that that one event emanated. What pulled him out of almost killing himself was that the guy who killed the younger son came up for parole. He went and spoke against him getting out and then realized he had to live for his grandkids.

I still think about that dude regularly, grief is so f*****g powerful it pulsates out and destroys if you don’t have the right support.

#7 I normally defend construction defect and personal injury matters, nothing too crazy. Early in my career we got a case involving a husband and wife who ran a foster home and one kid was alleging the husband had molested them.

Image source: oldjack, MART PRODUCTION / pexels (not the actual photo)

I was assigned to defend only the wife under their homeowners insurance policy. The allegations against the husband were bad, but the wife had no idea what was going on. Here was this poor woman, who was also a former foster child, trying to give back and help other foster children in the system, and now she finds out her husband is a child molester. It was heartbreaking and we just wanted to get her out of the case. Then we get more documents and learn this isn’t the first child to make allegations. The dad had been doing this s**t for years and she knew it. Maybe she was involved, maybe she just ignored it, either way the whole thing turned f*****g gross. I instantly wanted nothing to do with it. A few weeks later, my boss (the coolest guy ever) comes in and says he gave the case back to the insurance carrier, thank god. That was the only case I’ve ever felt morally opposed to handling.

EDIT: I should also clarify that once a lawyer takes on a case it’s not that easy to just say “actually I changed my mind”. I don’t know what my boss did to get rid of that case but I’m glad he was equally grossed out.

#8 Back in the day I investigated and later in my career prosecuted lots of arsons so I worked a lot of fire cases. One time the crews roll up on a garage fire. They are met by the home’s resident holding a blood-soaked towel to his crotch.

Image source: anon, Aleks Magnusson / pexels (not the actual photo)

The medics get him stable and transported. He later tells us the voice told him to eat a whole box of saltine crackers without drinking any water and he was like ok, and did that. Then the voice told him to eat the newspaper and he was like check. Then the voice said to cut off his testicles with a can opener and he was like yep. Then the voice said set the van on fire in the garage and he was like you got it. He did all those things in that order, and there were the scene photos of the testicles right there on the garage floor.

We got him into mental health court and he did pretty well.

#9 NAL, but personally involved in this horrific case. The travesty of justice was a contributing factor to me dropping out of pre-law in college.

Image source: Patches765, Luis Quintero / pexels (not the actual photo)

Adding a spoiler tag because this is pretty bad. If there is a trigger warning, assume it applies.

>!In the late 80’s, my uncle was convicted of violently raping over 30 children, myself and my youngest sister being two of the victims. During the case, my mother screamed multiple times that we were liars (especially when I testified) and trying to ruin his life. It got to the point where the judge asked her to quiet down or leave the courtroom.!<

>!The youngest victim was 3. The eldest in their 20’s. A majority of the victims on record were dead from suicide or imprisoned for d**g use. Two boy scout troops were found to have all been victimized.!<

>!During the trial, he also admitted to having sex with animals (dogs, cows, sheep). The church (LDS) was VERY involved in his defense, as he was an elder of the church. We lured him away from the path of God, and he couldn’t tell right from wrong.!<

>!He was sentenced to six **months** in a mental hospital. He got out in three, after “finding religion”. Even though he was an elder of the church.!<

>!His hoarder apartment had to be cleaned out by me, aka one of his victims. His bank accounts were non-existent, despite me supplying evidence they were opened under false names. My mother repeatedly told police I was lying, despite her brother’s own confession in court.!<

>!She ended up cleaning out my bank accounts (after already draining them bit by bit over the years) and giving him and the church the money because I “ruined his life”. And she welcomed him back into her home where he continued to abuse my sister until she moved out. !<

Since I know there will be some questions. Yes, I am in therapy at this time. Yes, the judge was from the same church. I’ll try my best to answer any others that come up.

#10 I’m an interpreter not an attorney, but I had a school case to interpret regarding bullying. The school decided to have a court case decision made in house. It was 12 kids and their parents on a stage in the cafeteria.

Image source: SwtPvega5_, RDNE Stock project / pexels (not the actual photo)

The school officials were there and a school advocate who acted as judge. Apparently the seniors would trap the freshmen in a designated bathroom after lunch and jump them. Four seniors and eight freshman who were beat up individually, there were supposed to be nine but one was in the hospital. They showed surveillance of how the seniors picked the freshmen to beat up and there were 2 teachers aware of this, in one of the videos one of the teachers helped the seniors by pointing out who the freshmen were. This was a hazing technique that was going on in this school for years but this case was to make an example of those involved. The teachers involved were only mentioned when the bullys admitted receiving assistance in pointing out who to beat up, the teachers never got in trouble. Only one bully was expelled and all the freshmen were suspended. It was unjust and sad. This case went on for 3 days and each case lasted 3 to 5 hours after school.

#11 I used to work as a legal secretary for a personal injury lawyer. He told me about a case where his client had radiation burns from an x-ray machine. In the avalanche of documents he received from the defendant during discovery, he found an internal memo. The memo described a serious problem with the machines and continued: “This is an issue we can’t ignore… unfortunately, it’s not in the budget”.

Image source: AmbitiousSquirrel4, Maryam Kamavova / pexels (not the actual photo)

When the case went to trial, he told the jury, “Show them they need to put this in the budget next time.” The jury complied, handing down one of the largest verdicts California had ever seen.

#12 Legal assistant here. Worked on a case where a male nurse sexually assaulted bedridden patients at a low income nursing home. F*****g horrifying. One of the women had a hip fracture.

Image source: CoffeeSpoons33, Jsme MILA / pexels (not the actual photo)

Worse part is that they complained to staff and no one listened to them for the longest time because they were old and didn’t have a lot of family. We represented the women and were suing the nursing home, and in our research uncovered tons of other lawsuits across the country alleging all sorts of negligence at other nursing homes runs by the parent company (called SavaSeniorCare, if anyone wants to know where to never send their older relatives!).

#13 I was dating a nice woman back in 2016. In our first conversation, I asked her what she did for a living. She was a paralegal for a malpractice firm at the time. I asked her if there were any interesting cases happening. She said “Yes, one we are going to lose.”

Image source: ManThatIsF**ked, cottonbro studio / pexels (not the actual photo)

I was interested… I asked what happened.

She told me “Well, we are defending a doctor who made a mistake. One of his patients was suffering from an eye condition that required a unique recovery. After surgery, the patient had to lie face down for the entirety of their day to prevent further eye damage. It had something to do with eye pressure and a gas buildup near the back of the eye. As it turns out, the patient wanted to fly on a plane and would intend to keep their eyes down through the whole flight. The doctor we’re defending didn’t tell the patient that they couldn’t fly during the recovery.”

The next part definitely sucked. When the patient took off on the plane, everything was OK. During descent, which people with ear problems can attest, the rapid change in pressure f****d up this patients condition. They went completely blind in both eyes due to the descent of the plane.

Predictably, the doctor did lose the case. It was a definitely an interesting first conversation to have with someone.

#14 I told this story on r/lawyers a little while ago, but I’ll tell it again here.

Image source: Moonsight, Kindel Media / pexels (not the actual photo)

I’m an immigration lawyer. I do mostly VAWA and asylum, but I handle other stuff on occasion.

I had a prospective client come in a few weeks ago. He’s interested in pursuing a relatively straightforward application. He tells me that he might have a criminal history that could affect his immigration. It’s only one arrest though, he says. It happened in 19XX. And it’s not serious.

“OK,” I say. It happens. Nobody’s perfect, and a single arrest is generally not a deal-breaker.

So, as I’m talking with him, I decide to Google his pretty unique name. A news article comes up, from his country, in his language. It’s dated the same year he said… 19XX. Hm.

I ask him: “what kind of crime did you say it was?”

“Oh,” he says, “I think it was d**g related.” I figure, alright, marijuana arrest or something: nothing we can’t overcome.

I click through to the article. The photo on the article sure looks like a lot like the prospective client. Turns out, prospective client’s arrest was not for marijuana at all. It was for cocaine. And not a little cocaine. This guy was caught attempting to smuggle XX *pallets* of cocaine. I must have looked a little bug-eyed, because the guy gave me a sort of sheepish look and a shrug.

Hm.

I tell the prospective client, maybe we should start by filing a few FOIA requests (Freedom of Information Act Requests) to see what comes up, and we’ll go from there. He agrees, and that’s that.

I’ll double check my suspicions against the government record, and let the client know what can, or cannot, be done.

Suffice it to say, getting caught smuggling multiple pallets of cocaine is not a small-time arrest. But, you never know what is or isn’t true, and you should always do your due diligence.

#15 IANAL but periphery of a divorce; anesthesiologist and his wife; dude has tons of money and a huge secondary stash of gold and other non currency assets that he doesn’t disclose; keeps lowballing wife and she keeps arguing for the proper financial disclosure – he laughs as she has to keep paying for her attorney to file to get access to the assets that he won’t disclose and they can’t prove –

Image source: DeepBlueSomethings, cottonbro studio / pexels (not the actual photo)

He kept lowballing her and refusing to settle all while he continues to make huge money and she struggles – he dgaf – he wanted to win and make her suffer and drag it out

Divorce initiated because of his infidelity.

#16 I’m not a lawyer, but I work closely with a lot of lawyers and see the same stuff they do.

Image source: anon, cottonbro studio / pexels (not the actual photo)

There was a case where a lady had been a victim of human trafficking and was kidnapped in her home country and sold into a prostitution ring in the U.S. She escaped, applied for asylum, told the FBI and whatnot everything she knew about her kidnappers and the others who bought her (putting her life in major danger), and was told that’s all it would take to get her asylum and permanent residency taken care of.

F*****s still tried to deport her. Don’t worry. She won her case, but only because one of the top attorneys in New York (if you know of a lot of attorneys in NYC, you’ve probably heard about this one) took the case on pro bono. It was wild to me how hard ICE fought to get her sent back and how intense that case got.

#17 It was a family law matter. I was a newly-minted attorney who couldn’t find work in the early 2010s and took anything that came to me. It was a custody battle. I represented the mom.

Image source: Achleys, RDNE Stock project / pexels (not the actual photo)

The dad lived with his father (grandfather) who had been convicted TWICE of r*ping other grandchildren. Easy case, right? No. Because Mom absolutely forbade me from bringing the grandfather’s convictions before the judge. Said he made ‘some mistakes,’ and while she wanted full custody, of course, she felt bad that grandfather’s ‘past mistakes’ might be used against him in the future, forever. I brought it up to the judge anyway. She fired me on the spot, during oral arguments. She ended up suing me. It was a mess. Would do it again.

#18 Slayer statute, interpleader case in federal court. Client murdered her husband to collect insurance proceeds. Found out that she promised to pay 2 dudes to bind his hands and feet with duct tape, execute him, and burn him in an alley, for $20k each, to be payed out of the insurance funds. She lost.

Image source: roymunsonshand

#19 So…I see a lot of messed up injuries in my line of work (personal injury.) like permanent metal in people, scars, mental trauma. Videos of car accidents, broken bones, you know, messed up stuff.

Image source: PizzaNoPants, Antoni Shkraba / pexels (not the actual photo)

But what gets me the most is health insurance companies. Basically, let’s say you have Kaiser, you get hurt they pay the bill. Unfortunately, if you get hurt by another person and recover funds from them, then your health insurance company (or workers comp) is entitled to be paid back from the money you get. Oh and the government gets first dibs too if you have Medicare or state funded health insurance. However bad you think the system is working, trust me, it’s worse.

#20 My sister is a criminal defense lawyer. She told me about a case where this guy had committed murder and after a week couldn’t take the guilt and handed himself in.

Image source: cheesecakefairies, Ron Lach / pexels (not the actual photo)

Only when he got to the police station and confessed, they asked him where he killed this woman. He told them and they said it was out of their jurisdiction and to go to another police station to confess because it was closer to where the crime happened.

So he left and went the next day instead. Noone looked for him or asked or anything. It went completely unreported.
He did hand himself into the police station and they began to start proceedings for a case against him.
They wanted to include on the report the fact he had been turned away from the police station and still handed himself in to show some sort of character but the judge and police said they wouldn’t allow it because it makes them look bad. They said they wouldn’t let the jury even hear about it. My sisters team was frustrated and horrified.

This was in Ireland.

#21 I will answer for my lawyer friend because he used the words, “This is the most f****d up case I’ve ever worked.” Basically, my friend is a prosecutor with the DA’s office and was assigned a child sexual abuse/torture case. The defendant was the child’s step-father.

Image source: omglookawhale, Pixabay / pexels (not the actual photo)

The abuse happened from the time the child was 9 to 14. She’s 17 now and testified to all the things her step-father did over those 5 years.

The “f****d up” part came when the defense attorney tried to blame the girl for “allowing” everything to happen to her and of course, since the girl is now a very attractive teenager, used the “she was just too sexy and biologically, the step-father couldn’t control himself” defense.

My friend was watching the jury while the defense was cross examining the girl, and saw so many head nods as though the jury agreed with the idea that a kid in 5th-8th grade allowed herself to be constantly r*ped and tortured.

Thankfully, the jury did decide to convict the step-father but it took a lot of work, partly from myself as the girl’s therapist and expert witness on child abuse and delayed outcries, for the jury to convict.

I think both my friend and I lost a little bit faith in humanity that day. Both after hearing the defense and seeing certain jury members agree with the idea that a child consented to any kind of abuse.

Now the girl and I are having to continue therapy. While she’s done an incredible job working through the abuse, she’s now exhibiting trauma symptoms from testifying in court.

#22 My mum’s ex-boyfriend had to defend a triple-murder with kidnapping. Two of the victims were a mother and her three-year-old son. Defendant had some kind of psychosis, I’m not sure what. He attempted to carjack a fourth victim who was able to overpower him, leading to his arrest. Said ex-boyfriend switched to prosecution after that.

Image source: Porrick, Alex Qian / pexels (not the actual photo)

#23 It was a labor case, in which in the middle of the hearing, the judge (60-year-old male) started to flirt with my client (23-year-old female) in a direct, straightforward way. It was SO shocking that was one of the only cases I got speechless in a trial. Those hearings are closed here in Brazil, so no jury, no recording — nothing.

Image source: alekdefuneham, Sora Shimazaki / pexels (not the actual photo)

#24 Legal Videographer here…

Image source: zekthedeadcow, Pixabay / pexels (not the actual photo)

Grand Parent Custody case where the dad got photographed molesting the 8yo daughter under the Christmas tree. Kid goes for a medical exam and the doc reports extensive injuries usually associated with sex abuse. Then checks a box to indicate the injuries were not related to abuse. Police say nothing they can do about it because of the checked box. The mom ‘commits suicide’ “because the dad didn’t want to sleep with both at the same time” according to him… and the person holding the gun when she shot herself gets a misdemeanor iirc. Police lose two polygraph tests and a couple r*pe kits. Grandparents lose custody case… oh his dad was a magistrate in the same county… and the dad gets full custody.

Unfortunately that day when I got home r/eyebleach had a series of infant and toddler photos instead of kittens and puppies.

#25 Not a lawyer, but I got a summer gig once sorting -/alphabetizing case files at a law firm and throwing out the files that were more than 7 years old. This necessitated going through them occasionally to find the closure dates.

Image source: coleosis1414, KoolShooters / pexels (not the actual photo)

The saddest one I picked up was a 17 year old boy who got sent to jail for having sex with a 14 year old girl.

Not that I think it’s okay for a 17 year old to have sex with a 14 year old; that’s realllly pushing it to put it mildly.

What made me sad was the way that the prosecutors procured a confession. It was one of those “if you write a nice apology letter to her parents, maybe we can make this all go away” manipulated written confessions. It was this heartfelt letter that was all
“I’m so sorry I put your family through this hardship, I wasn’t thinking, it was irresponsible, etc”. — and it just had this soulless sticky note on it that just said “CONFESSED” in all caps.

I read lots of interesting case files, but that one was a gut punch. The kid did some time for that one.