14 Honest Lawyers Share The Cases That They Actually Regret Winning.

Lawyers of Reddit were asked: "What cases are you sorry you won?" These are some of the best answers.

1/14 My father is a lawyer. I asked him once why he didn't do family law anymore. He told me about a case where he was able to get a father full custody of his children. But by the end the of case my father wasn't convinced that his client wasn't molesting the children.


2/14 I was defending a man who allegedly sexually abused and raped a 7 year old girl, and because the police screwed up on some technicalities when arresting him, he walked away as if nothing had happened. I took the case because of some political compromise I had at the moment. Not proud of it.


3/14 A while back I represented credit card companies suing for outstanding debts where we had pretty stringent client guidelines dictating how we handled lawsuits. The bottom line was that we were to be aggressive in court so as to put our client in favorable positions during any settlement negotiations. One defendant was a 40 year old woman who had maxed out all her credit cards in a futile attempt to pay for healthcare for her husband, who ultimately died of cancer. In total, she had spent something along the lines of $60,000 paying for chemotherapy, hospital stays, and various other bills. She ended up losing her job, husband, and home, all within the the span of 3 months. She didn't even bother showing up for hearings or responding to the complaint, meaning my client won a default judgment against her. The worst part? I had to stand up and tell the judge what my client was entitled to: $60,000 for principle amount, $80,000 for interest and late fees, $10,000 in attorneys fees. She now has a judgment of $150,000 against her. I refuse to do that line of work anymore and have made it a point to represent people against credit cards if the opportunity presents itself.


4/14 Had to take a house from an 18 year old girl who basically spoke like Juno (I liked her), and was paying the bills on behalf of her mum, and her dead beat dad (who had run out on the family). She had like three younger siblings, and just wanted to keep things together for them. She sounded so put together, and sacrificed going to uni to get a full-time job for them. It sucked so bad...


5/14 Prior to law school I worked for one of the largest debt collection firms in the country. I was in a department that only dealt with post-judgment executions... levying real property, property liens, raiding bank accounts, wage garnishments, you name it. Needless to say, if you were talking to me you were pissed. I did it for about 6 months and swore to myself I would never go into the field after graduation.

I felt so bad about it that I work pro bono once a month at a local court to give credit advice to people being sued by collection agencies. Whenever I see that company's name in the caption, I work as hard as I can for that defendant. I once freehanded a 20 page motion to reargue for a man that didn't speak English and smelled like he was allergic to showers. That was still a more enjoyable experience that working at that firm.


6/14 I had to go to court and argue against a woman in her 50's who had signed as a guarantor for her son. He took the money, stopped paying, and left the country. She lost her house, the only thing she had left, because of her estranged son who she wanted to get closer to (and hence become his guarantor). It was horrible.


7/14 Worked for an insurance company. A widow sued them after they denied paying the indemnification for her husband death. The man had hanged himself in a barn and the company denied the payment because under the law in effect back then, voluntary suicide would void the insurance. It was a poor family and the loss of the husband really got them.

However, the widow had a strong claim based on the fact that the man had some mental issues. In fact, the man had experienced a severe condition of amnesia in the past to the point of leaving the house and wandering around for a few years before being found and taken back to their farm house. This would strongly support her claim that the suicide was not voluntary (i.e., the man was not in full mental condition to actually discern what he was doing).

Anyway, we had to do our job so we dug deep in the case. We started to talk to people around town and eventually we came across the police officer who answered the call when the man was found hanging. He told us that a note was later found beside the body. We managed to work with the bureaucracy and was able to get the note.

The note said something along these lines: "My beloved wife. I hope you will forgive me, as well as X and Y [his sons]. I could not find any other option to pay the creditors, but hopefully this decision of mine can help fix all the troubles I caused you. Please, don't forget to pay Mr. Z and let him know I was very grateful for what he did to me. I love you all".

Well, we filed the note in the lawsuit and the judge concluded that the man knew exactly what he was doing and had the clear intention of causing his family to receive the insurance money. The claim was denied and after a few months someone told me that the widow lost her house and her lands to creditors and simply vanished.

This really troubled me and I seriously considered quitting, but in the end I just terminated my agreement with the company and moved on to other cases.


8/14 I do patent law. Often I think it sucks that I have defended a patent that if the patent didn't exist lives could be saved for much, much cheaper (or free).


9/14 Two sentences I wrote as a junior associate ended up verbatim in the brief and then in the US Supreme Court's majority opinion in AT&T v. Concepcion. That's the case where the Court ruled you can't have a class-action suit if there's an arbitration clause.

Basically, the ruling means that a savvy corporation can screw all of its customers as much as they want, as long as each individual claim isn't worth arbitrating, and the government won't let you do anything about it. This is a big dealwhy isn't anyone rioting?

I didn't even know what the research was for when I wrote that memo. But I still feel guilty about it. It's like the guy who cleaned Hitler's horse stables. It wasn't bad in itself, and someone would have done it anyway, but I still ended up supporting something evil.

I quit a few weeks after writing that memo and went into plaintiff's personal injury work. I have never regretted that change for even a moment.


10/14 Not a case, but there were times where I would negotiate things a client wanted in a video game contract that I knew would make the game worse. That hurt more than anything else.


11/14 We / I went to court and slammed a guy who claimed to be representing a guy that owed money to the bank (around $100K) in loans. He'd always paid his bills, but had disappeared for around a year. A friend of his asked us for more leniency, and was sure he would come back and was probably in a hospital or something. We won, took his house and sold his possessions. We got a call a few months later from the guy, he was in a coma (listed as a John Doe), his bank account didn't work, had hospital bills to pay, and his house was sold.


12/14 I'm an attorney in South Africa. When I first started practicing, I worked at a firm that represented a huge international medical indemnity society. This meant that we exclusively defended doctors who had been sued for medical malpractice.

One doctor in particular, I will never forget. I'll call him Dr P. Dr. P is a specialist gynecologist and obstetrician. During my two year stint at the firm, Dr. P killed (or at least his gross negligence was responsible for the death of) 4 women.

The first two died because he perforated their bowels during hysterectomy procedures. The third died when after he stitched the patient up so badly following a cesarean, the wound collapsed and went septic resulting in organ failure. The forth patient/victim died as a result of Dr. P sewing her uterus to her bladder. I do not have a clue how the f*ck a doctor can unknowingly do that, but he somehow managed...

Thing is, Dr P worked at a public hospital, which keep no, or virtually no medical records and the conditions are terrible. It is thus incredibly hard to compile thorough, damning evidence against the doctor.

In all four, we defended Dr P successfully with applications for absolution from the instance. Eventually, I considered how I could warn people about Dr P, without breaking attorney-client confidentiality, but there was no way. It haunts me still that he is practicing...


13/14 I represented the woman in this. Guy and girl live together for a decade as a couple decades ago. She cheats on him so he leaves town after being together for 5 or so years. He ends up moving to Michigan and ends up getting a good job building cars. The guy ends up retiring a few years ago and gets some kind of ERISA money from his pension. Whorebag finds out about the settlement and ends up suing and getting half of the $ because she was his common-law wife.


14/14 Divorce case. Custody battle. I represented the wife. She cheated on her poor husband during the marriage. I thought the case was lost after they played a tape of her with the other man. As a last ditch effort, I figured out she wasn't 18 when the marriage contract was signed, so it was voidable and she got full custody. I did all this while following the lawyers ethical code. I didn't say a single lie that day.



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