20 Lawyers Express The Darkest Cases That They Won But Wish They Didn’t

There are some cases that lawyers wish they never won. These are the cases that still haunt them to this day. They may have won the case, but the victory did not bring them any sense of accomplishment or satisfaction. Instead, they are left with a feeling of regret and guilt.

#1

My mother was a prosecutor for thirtysome years. The worst case that still haunts her was of this fifteen year old girl who was a fat Asian girl who got pregnant. So she hid the pregnancy the entire time from her very abusive parents, gave birth in her bedroom without them finding out, then hid the baby in the closet and it died from suffocation. Clearly the teen was horrifically in the wrong, but she was so beaten down and abused and terrified of her parents my mom wished she could have charged them instead and let the teen have a normal life.

Image source: GeraldoLucia, Louis Galvez

#2

Did a divorce where the husband (who I was representing) wanted to trade custody of his children for a set of bedroom furniture. The bedroom furniture was not even like a family heirloom. It was furniture that you could probably get at a Rooms-to-Go or something. Ugh, still makes me ill. That’s why I got out of family law.

Image source: mintrawr, Kenny Eliason

#3

Family law is a little different in that you never really “win” per se. You may get more favorable rulings or better terms, but unless the opposing party did something illegal or mindbogglingly stupid it’s never a decisive “win” really. Although I did have a case where my client fought really hard for the dog, and then ended up turning him over to a shelter. F*****g a*****e. The ex wife received an “anonymous” tip and was able to get him back quickly.

Image source: anon, Andrew Wise

#4

I recently saved an insurance company $2,000 on a settlement with an injured person. Not as exciting as the rest, but it’s one of those quietly sad moments where you question why you even went to law school in the first place.

Image source: charmcharmcharm, Towfiqu barbhuiya

#5

A divorce and the wife (who I was representing) wanted to give away custody of her 2 children to her husband who clearly didnt want them for her 3 million dollar yacht. Personally I would have her keep both the 3 mil and her children. I still regret winning that case for her.

Image source: spicy_mountain, Viespire

#6

Did a simple eviction for non payment of rent just last month. Super easy. Won the eviction but found out after the hearing that she didn’t pay because her cancer treatments we eating up all of her income.

Felt awful but worked out a deal after the fact so she kept the apartment.

Image source: sailingawayagain, Alexander Grey

#7

One of my cases I can remember well is one about a man who was accused of a sexual crime toward a women. His story kept changing and we all knew he had done it but he wouldn’t admit to it so we went on with it. Somehow he had evidence on the women and ended up winning the case. To this day it scares me to know he’s out in the world probably doing it again.

Image source: Awesomegen01, Sergiu Nista

#8

I’m a work comp attorney. Now represent injured people, but used to work on other side insurance defense.

There was an applicant with a serious injury. Fell off a ladder, busted back with fusion, shoulder f****d, years of treatment. Internal issues, psych issues – really just f****d up. 50%+ permanent disability. We were 5 years in and finally getting to settlement time. If we bought out his future medical, settlement pretty far into 6 figures. This guy was the sole provider for wife and 2 kids.

Then we found out he had a aggressive brain cancer. Expected only couple years to live, at best.

Thus, we wouldn’t buy out future medical anymore. Still got permanent disability for $60k-ish… but can’t give medical buyout based on 25+ year life expectancy anymore.

I felt terrible for the guy and his family. Me and the adjuster tried to get insurance to agree to some sort of amount like 5 year buyout, but the bean counters said hell no. The attorney knew it wasn’t me making the decision. Even though he worked on that guy’s file for 5+ years he decided to take $0 in fees. I have so much respect for that attorney turning down $10k+ in fees to help his client in a very s****y situation.

Image source: dieabetic, cottonbro studio

#9

Image source: chamtrain1, DANNY G

I have handled my fair share of domestic abuse cases….about 90% of which end with dismissals. I never like winning them, but almost always do.

#10

Settled a personal injury case for a guy and he was set to get about $5000. He was in jail. I held the money for a couple months and when he got out he came by to get the money without delay. The next day the cops came around and asked if I knew him. I explained that I did. I was told he died that night of an overdose and the only thing found on him was my card, some drugs he had not yet used, and a needle.

Image source: anon, Quỳnh Lê Mạnh

#11

I got a spoiled brat of a teenager cleared of a shoplifting charge when he absolutely had done it. His rich parents hired me to represent him, I did that to the best of my ability, and we went to trial and won, but I can’t say I felt good about it. This kid needed to be taught some accountability for his actions and his parents just wanted to buy their way out of any trouble he got into.

Image source: unbelievablepeople, Nipu Gs

#12

I successfully got a kid kicked out of a very good school district because the single mom didn’t live in the Distirct and wanted her daughter out of the shut district she was in. We proved it by videotaping the kid leaving another house outside the district on 7 different occasions.

I was a brand new attorney and had to take the case.

Still feel bad about that.

Image source: LawyerLou, note thanun

#13

Prosecuted a murder case. Twenty one year old kid starts dating an older guy’s ex-girlfriend. The older guy (real roughneck, loose connections with a local biker gang) was going all over his small town talking about how he was going to kick the kid’s a*s. The older guy sends some nudes of the ex while he’s getting drunk at a bar, so the kid says something smart a*s in response. Older guy comes to the kid’s house to fight him. The kid shoots him once, and the older guy dies. Jury didn’t buy self-defense or castle doctrine. Convicted of voluntary manslaughter. Twenty years. Burned up his appeals with no luck.

I have a son about the kid’s age. I could totally imagine him doing the exact same things if he were in a similar situation. S**t’s going to haunt me until I die. No doubt about it. Started thinking about other work the moment the verdict came back.

Image source: Quijanoth, JC Gellidon

#14

Late post so this will probably get buried. This is another family law story, using a throwaway because some of my colleagues use Reddit.

Summer of 2018 I get work regarding what seemed, from the client’s description, a pretty drawn out and messy divorce case. The husband was my client, and he made it seem, very adamantly, that his soon to be ex-wife was after his every penny. Given he seemed to have a fairly high paying job, it seemed like a pretty common type of case, the city I work in has many instances of this, it has a high cost of living and a lot of well-paid working professionals in private industry. He was a very well spoken, amicable guy in his late 50s, and truly seemed like he’d been taken by surprise and betrayed by his soon to be ex-wife.

When I actually got to the case, however, I was basically floored.

His wife was a working professional as well, worked in government, they’d been married for over twenty years and had two kids together, and a paid off house. Before taxes he made almost three times what she did, not counting his stock options, and yet she’d contributed equally to their mortgage on every home they’d owned over the course of the marriage. By all accounts, despite a vast difference in income, she’d carried her weight, raised two kids, and worked full time during the entirety of the marriage. I live and work in Canada, she could have *easily* raked him over the coals in the divorce if it had gone to court.

Instead, it seemed like she’d done everything she possibly could to not have him subjected to that. This divorce had been ongoing for five years before he hired me, and it was basically him looking a gift horse in the mouth over and over, a constant renegotiation on the contract they’d both signed initially, with him skimping on alimony and then debating on lesser terms. He was basically given an inch and tried to take a mile, dragging it out for so long that per divorce law it *had* to go to court. I almost suspect he did so as a way to try and drag her through the mud, though he may have genuinely been that delusional.

I consider it a win only because his ex-wife was adamant about only wanting what was somewhat fair, and for it to be over because of the strain it was having on the family. Per the contract he owed her, still, about 50k in backpay, but she was content with 15k, which was less than this guy made in a month. I did regret the ‘win’ though, she seemed like a very nice woman with the patience of a saint, while almost all of his anger towards her seemed to come from wounded ego.

Edit: I should also note that though they had two kids together, both were in their 20s by the time I was hired, and custody had never been an issue at all, even for the one who had been a minor when they’d separated.

Image source: LawT-Away, cottonbro studio

#15

I represented this construction worker in a divorce. The wife stayed at home with the kids and had no money. Through entire divorce her attorney claimed that my client was hiding money. They had no evidence and the client vehemently denied it.

We had a good settlement in the case and I considered it done. When they client came in a few weeks later to pick his file he thanked me for my work and said “and she never did find the money I hid” he had a big laugh and walked away.

What a d**k.

Image source: Hiredgun77, Collins Lesulie

#16

In one of my first cases after passing the bar exam, a young man retained me on a drunk driving charge. No one was hurt, but he totalled his car.

During trial, the arresting police officer testified that my client was clearly drunk at the accident scene, and that my client was loudly blaming the accident on the f*****g a*****e who stole his car, crashed it, and then fled before the cops arrived.

However, according to two other witness statements tendered into evidence, it was my client’s friend (the passenger) who was screaming about the a*****e who stole the car, not my client (the driver).

The cop must have confused the two men during his testimony.

This discrepancy raised a reasonable doubt in the judge’s mind, so she acquitted my client.

At the time, the acquittal was somewhat unexpected for me (in my personal view, my client was clearly drunk and responsible for the accident, regardless of who was blaming the mystery a*****e to the cops), but I was happy my young client got off, no one was hurt, and lessons were learned. And I was quite euphoric to have won my first criminal case.

The regret? About a month after the acquittal, my young client called me at 3 am from the police station saying “it’s me again! The police arrested me for drunk driving again! Can you help me?”

Not only did I answer no, I instantly regretted getting the earlier acquittal. My client apparently didn’t learn any lessons…

Image source: Horrified_Witness, Gabe Pierce

#17

As a former employment lawyer I regret defending a company in a law suit in which the employee had an acident and lost her left leg, had the left side of her body covered in burn scars because of the companies fault.
The case was more or less like this.
This lady worked at a toll on a highway, whenever she needed to go to the toilet she’d have to close the toll, change the sign lights to red so no-one would go through that toll.
Unfortunately due to lack of maintenance, the lights did not change and when the lady was crossing the road a car ran her over, dragged her 10 meters.
After defending this case I realised I did not want that in my life, I wasn’t meant to be a lawyer so I dropped everything and quit the week after.

Image source: just-wanna-vent, Andrea Piacquadio

#18

I do juvenile work, criminal law and family law…

I represented this client first when he was a juvenile charged with disorderly conduct at school and fighting, then when he became an adult it for was for simple things like possession of marijuana.

As he got older, it became easier and easier to figure out what part of his life hasn’t gone as well as it could and I tried to counsel him and push him to better himself.

He got his GED, he started going to NA, he started classes at a community college, and found a part time job.

On the night of his 21st birthday, he was charged with a DWI. Of course I’ll take care of that too.

About 6 months later, we are due in court for trial (on a Monday) and he doesn’t show up; which at this point in his life is highly unusual.

As I’m trying to figure out where he is, the court starts going over Arraignments/First Appearances and then low and behold three people are up for Murder charges. The prosecution starts to tell the judge what the facts/circumstances of the case are and mentions a few victims names.

Apparently, my client was at a party when these three individuals decided to allegedly do a drive by shooting. My client suffered multiple gunshot wounds and didn’t make it to the hospital.

So… by default, as you can’t prosecute a dead person; the State has to take a dismissal. I guess technically a win.

Either way, it was crushing to me as I thought he had really turned his life around. (He had)

EDIT: Wow, this really blew up. Thanks for all the positive comments. And the bling.

Also, since some people asked for clarification or were confused.

1: I truly believe he was on the right path forward.
2: GED = High School Equivalency Diploma
3: NA = Narcotics Anonymous
4: DWI = Driving while impaired

Image source: phitheta219, why kei

#19

I do family law and I represented a father who had lost most of his custody from heroin use and imprisonment as a result. He came to me saying he was clean and doing good and had his life together and it checked out. He had been clean for almost nine months not counting jail time and seemed sincere in wanting to resume a full relationship with his son. The other side fought viciously to keep him at extremely little custody and supervised at that, but we prevailed and got an order restoring fairly frequent unsupervised partial custody.

Not long afterwards, only about three months after the case, he was back doing heroin, sold most of his furniture, and for me the most soul-crushing is that he set up a fake GoFundMe stuff for his child’s “cancer” (his child didn’t have cancer and has never had cancer so you know where that money was going). I withdrew my appearance at this point so I don’t know what happened afterwards, but I imagine and hope his custody was taken away.

Basically the net result of winning that case was that the poor boy had to witness his father relapse on heroin and was exploited for money. Worst case I ever won.

Image source: DemonFirebrand, Bruno Aguirre

#20

Image source: mrfixit420, Josh Appel

I helped represent a slumlord in a lawsuit regarding discrimination in public housing based on disability. The state was representing the disabled tenant.

The facts were pretty clear, slumlord discriminated on the basis of disability.

Our state doesn’t have much case law regarding discrimination in housing based on disability. So the state was really hoping to get make case law

We ended up sowing enough doubt to survive the tenants motion for summary judgment. Knowing that the tenant needed money, we made an offer for a decent amount of money for a disabled tenant, but peanuts for the slumlord.

I imagine the state wanted to proceed to trial, but the tenant needed money and accepted.

By gaining the best outcome for our client, we allowed the slumlord to get off basically scot-free and deprived our state of needed case law.