Lawyers like to win. It’s kind of their job.

If I needed a lawyer, I’d want one with an overwhelmingly positive win to loss ratio. Wouldn’t you?

So, it would stand to reason that most lawyers remember the cases they lost with a fair amount of regret.

But that doesn’t make for a good article.

You want to hear about the cases they WON that keep them up at night.

And, thankfully, so did the people at AskReddit who were savvy enough to pose the question to their users.

Here are 16 of our favorites.

The first one is cheap, but cute. Then it starts getting dark pretty quick:

1. The Kid Lawyer

I played lawyer on the playground in elementary school once. A kid had borrowed a few bucks from another kid and then tried to deny it a week later. Normally this would just get you called a jerk and avoided in the future, but the loaner wasn’t wanting to do this. I told him that for a dollar, I’d devise a plan to get his money back. He agreed.

I told the loaned kid that the loaner was mad as hell and was going to punch him if he didn’t have his money back by the end of the week (it was Wednesday). He still refused. I told the loaner to punch him come Friday if he didn’t have his money. Punches were thrown AND money was paid back. Never got my dollar though, so that’s why I regret it.

2. “Fatal Dependency”

It was a fatal dependency claim. Mother with 5 children, loving father taken away by my client’s negligence. When it came to pay the dependants, I discovered that the children weren’t the deceased father’s. Wife had affairs and fathered children to other men.

We paid her children nothing. Two days before the conference where we outlined our strict position our client gets a phone call from dead father’s best friend.

Before the father died the best friend came clean about the affair with his wife. Father forgave him, told him that he knew and loved them anyway. We get out of paying these children anything, and I’ve always felt bad about it.

3. “Winnings”

I used to work in finance a while ago, and sometimes dealt with debtors who owed money. Some of the collection agencies I had to deal with were just outright scum. Most were okay, but some of them would describe with a tone that I can only sum up as glee, how they would sue everyone as hard as possible, because they’d get a bonus of the “winnings”. They seriously derived some sick joy in making people’s lives as hard as possible.

They fell into that small category of people where if they all died in some freak accident, the world would be a slightly better place. There was no humanity left in a single one of them.

4. Why Dad Left

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.

5. “Political Compromise”

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.

6. Two Sentences

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.

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.

7. Game Off

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.

8. “Stress”

I know an older successful lawyer who got a rapist off on a suspended sentence. He said the judge seemed swayed by the fact that the defendant had a high stress job managing about 200 employees, and basically gave him no punishment. The girls (there were 2) freaked out when they heard the ruling and the lawyer felt really bad. Did Not expect a suspended sentence but did too good of a job. He regrets it…

9. Common-Law

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.

10. “I didn’t say a single lie…”

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.

11. “Don’t bother…”

Not a win, but relevant.

I got a client, a legal aid dude where somehow the brief fall across my desk. The charge: Arson of his ex-wife’s shed

I meet with my solicitor who simply doesn’t care and is adament the client is guilty and this guy has generally got a really good gut feel about these things. We meet the client who insists that it is a frame job, that his ex-wife is trying to get back at him for some slight and is damning his good name.

The guy is adament and to my eternal shame, I believed him. I took the case to hearing and we fought it on the grounds that he wasn’t guilty.

Half way through, some evidence emerged about him being seen acquiring things to start a fire. I take him aside and ask him if he wants to vary his instructions because quite frankly, I still think we can do pretty well out of a plea of guilty.

The guy looks me square in the eye and with total and utter sincerity tells me that he is innocent, that he would never do such a thing and that he needs me to believe in him because people have let him down so often. For what its worth, I was 100% convinced of his innocence after that speech.

We finish the hearing and he is found guilty, I turn around to look at him and he has the ghost of a smirk on his face. He gets a very minor sentence, similar to what I would have gotten if we pleaded guilty at first instance which was better then I expected.

I tell him that since he is innocent, we can appeal the decision and take it before the higher courts to clear his good name.

The fucker just smiles at me and goes, “Don’t bother, I did it. It’s a fair cop.”

That’s the exact moment I stopped having any faith in my clients telling me anything other than lies.

12. “Sad Face.”

I once had a case representing a pharmacy that was suing a nursing home.

The pharmacy had a contract for exclusivity of supply with the nursing home and the nursing home hired a new contracts manager. The new contracts manager unilaterally made the decision to sever the contract and appoint a new third party as the sole supplier.

My clients sued the nursing home for $300,000 in damages (that a lot of medicine!) plus another $30,000 in costs and interest.

The nursing home folded, we divided up the remains with the other creditors and got basically 20c in the dollar, all of the residents in the nursing home had to find alternate accommodation and about 40 staff lost their jobs. I heard anecdotally that many of the older patients who were confused and had Alzheimers etc were VERY distressed about the move, crying and shaking etc.

The kicker – contract failed because they went out of business anyway.

Sad face.

Yes, that lawyer just said, “Sad face.”

13. K.I.A.

When I was in the military, assigned as the paralegal to my command, we had a simple case: An administrative punishment for underage drinking. However, at this time in my legal position, I strived to shine by recommending obscure/unknown charges be added, get the paperwork done in time to hit the next payday, pretty much be an asshole to service members go had just been caught for something (usually) trivial. Well life goes on, we deployed to Iraq.

Said service member was KIA. Guilt began to creep in. Why had I been such an ass to someone who was just enjoying some beer before going overseas? Then the real drama came. Reports had been coming in from the wives of the higher ups that this service member’s wife had been seen around town with a new supposed boyfriend prior to her husband being killed. We found out that before he had been killed he had already started the proceedings for divorce, but had not changed his life insurance policy.

A policy for $400,000 USD. This time I used the legal savvy and command backing to help his mother receive the money instead of his cheating and clearly moved on wife. After that case, I tried my best to see both sides of the story and try to just keep the recommendations to a bare minimum.

14. “Big, big difference…”

I was a law clerk during law school, I worked at a major metropolitan public defenders office. I quickly earned a reputation as something of a boy wonder on things like search and seizure issues, I was good at it (still am). Some lawyers in the office had a murder case and asked me to look at the file to spot potential issues. I quickly saw the police had come up with a clever plan to violate the defendant’s right to have a lawyer present during questioning, the prosecution made it easy to spot because they tried to be evasive about it preemptively, which only drew attention to their problem.

I nailed them in a memorandum to dismiss, that motion became a bargaining tool (the prosecutors weren’t worried about losing the issue in trial court, that wasn’t going to happen, but they were very worried about how the case would look on appeal, a fairly common scenario) and, long story short, the client got a sweetheart deal, didn’t even plead to murder and got a fairly short stint in prison. The lawyers were ecstatic and told me my memo had made a big, big difference.

For the purpose of my tasks, I had only been give the part of the defense file that dealt with interrogations and that sort of thing, the part that dealt specifically with the details of the alleged murder were not given to me. After the sweetheart deal was in place, I was given the chance to look at that part of the file, including police photos of the murder scene.

It was a cruel, cruel murder and the defendant was completely remorseless. This case has haunted me to this day and I swear to you, if I ran into this man today I would throw him off a cliff for what he did. So much for the glamor of criminal defense work, you can sometimes find yourself with a case where everything is rotten to the core. But that’s rare, thank God. Most of the time you are helping people who really deserve to be helped.

15. Concerns

Not sorry we won, but sorry for the young man who lost because he was receiving such bad legal advice and bad technical advice from an online forum. Through the course of the case, his deposition and his trial, I got to know the young man and honestly liked him and felt like he was a good, but foolish, sort of person.

I felt bad for him because he could never tell he was being given bad advice, and despite my efforts, I could never get him to realize he was being screwed by his lawyer and led astray by random strangers on an online forum who thought they were mechanical engineers (but were not, and who were saying our technical explanation was impossible).

The case involved his claim that his vehicle was defective due to a defect in materials or workmanship from the factory due a pin breaking 3 or 4 times in his turbo. Problem was, he installed a cold air intake and exhaust system, both of which were connected to the opposite ends of the turbo. Another problem, his was the only car in the country that was repetitively breaking these pins, and we did testing where we put the car back to stock condition and compared it to the modified condition, and our testing confirmed that the modifications were causing an increased vibration in the turbo, and said vibration was breaking these pins over time. Fairly straightforward.

From my perspective it seemed like a simple misunderstanding, and in order to fix the situation I convinced my client to make what I thought was a fair offer – we told him to put the car back to stock condition and if the vehicle had any problems we would give him a new car and pay his attorney’s fees, no questions asked. If the car didn’t have any problems, however, we would want him to dismiss his case. We also made a cash offer if he wanted some money in his pocket he could just walk away.

The problem was, in my state, the law he was suing under provides for statutory attorney’s fees and costs. This means that the defendant has to pay the plaintiff’s attorney fees and costs. This means the plaintiff’s lawyer isn’t really working with the plaintiff in mind, but only thinking about how he or she can run up as many legal bills as possible and try and force the defendant to settle. Complicating this case, if we were right and his modifications were causing the problem, if he removed them he wouldn’t have any more problems and we would want him to dismiss his case.

His lawyers realized that they would have no chance of recovering any fees if we were right, so they told him not to take either of our offers and we went to trial. We won at trial, and because we made a statutory offer to compromise and asked some targeted requests for admissions that he denied, we were awarded $30,000 in fees/costs of our own. Now, the guy owes my client more than what the car is worth, all because he couldn’t tell his lawyers were more concerned about themselves than him, and because he refused to accept our technical explanation based on comments from random strangers in an online forum.

16. Just Short

I successfully foreclosed on an assisted living facility against a sweet old lady who was running it as a family business with her teenage son after she scrimped and saved and pawned to pay to redeem the property but was about $1,500.00 short on the $80,000.00 debt. My client kept the redemption attempt and still took the place and kicked everyone out in order to sell it.