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.