Lawyers Explain Which Cases They Secretly Wished They'd Lost
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Being a lawyer, more specifically a defense attorney, is possibly one of the hardest jobs in the world, morally speaking. Besides being portrayed as the villain in almost every movie (outside of the cinematic masterpiece "My Cousin Vinny"), defense attorney's are burdned with the gift of knowledge. Knowledge their client they are charged with defending and proving the law may not have been the kindest on is, in fact, guilty. Sometimes not just regular guilty but extremely guilty. It must weigh on your soul in a way no one truly understands.

Until now.

Reddit user, u/99TwatsontheD, wanted to hear about:

Lawyers of reddit, have you ever done a case you secretly hoped you would lose and why?

Sometimes, You Just Need The Money

I worked at a civil firm and our biggest client for a while was a real estate investor who was the most unpleasant a--hole I've ever met. His favorite scheme was buying "distressed properties" (translation: unlivable sh-tholes) at foreclosure sales, selling them on credit to people who couldn't afford to purchase a house any other way, waiting for the buyer to fix the place up with their own money, and then finding an excuse to foreclose on them so he could buy the place back and sell it for more to somebody else. As you can imagine, this is wildly illegal and got him sued by many, many people.

Trying to defend this indefensible a--hole against the people he screwed was a nightmare, but I desperately needed the job. We dropped him as a client when he stopped paying his bills and I hope he winds up behind bars or bankrupt.


Reel Them In Then Change The Game

Defended a company that attracted a bunch of its employees with a profit sharing incentive scheme. After 5 years (when the incentives were due to be paid) they tried to change the definition of "profit" in the employee contracts so they could argue that no incentives were payable. I was neither surprised nor unhappy when the judge told our clients they were full of s***.



Oh yes! A high maintenance divorce client that was pitching a fit bc she was going to have to pay $60/month in child support. She wanted a recalculation and I was praying she would have to pay more!


In Trouble For Not Doing What You're Told

I prosecuted two cases against a defendant for meth possession. They were slam dunks...guy got arrested by the same officer at the same location and made the same admission. It was literally the same trial. He had several priors and faced a minimum of two consecutive prison sentences of 10 years each...he faced 20 years. I hoped he would be acquitted because (a) that is an insane amount of prison time for a small amount of meth, (b) he was a vet who was injured in combat, and (c) he was relatively young and had to use a colostomy bag.

My a**hole boss wouldn't allow me to deviate from the office policy plea offer. Defendant goes to trial and is quickly found guilty. He should have testified bc I wouldn't have objected to anything. The kicker was that when the first verdict was read, he let out a long, loud fart. It was the saddest fart I've ever heard.

He ended up getting 10 years total bc the judge ran them concurrently. After that, I got chewed out by my office for not arguing with the judge that he had to run them consecutively.


Pay For The A-Hole Privilege

Doesn't happen often, but when it does, it's usually because client didn't take my advice. Maybe client thought he could skip a certain step in a transaction. To save money (usually) or time (same thing). In those cases I am rooting for it to come back and bite them in the rear. Sometimes it does. Sometimes there are no consequences. Meh. You win some, you lose some.

Or if client doesn't pay his bill, I secretly hope he gets in a situation where he suddenly "appreciates my value." Or, in other words, I hope he needs me again real soon so that he'll pay up (and I can ask for advance fees due to past poor payment behavior).

Speaking of, if I'm working a case where client has unreasonable demands or expectations and I just don't want to do it (but I have to because ... reasons), I just bill the hell out of them. Some folks pay for the privilege of being an a--hole.


Milking For All Its Worth

My friend used to be a plaintiffs personal injury attorney, and he told me this story today about how he "lost" his client some money.

The client was trying to use his kid to get money from a car accident. Didn't just take the kid to the ER, he took the kid to a chiropractor, tried to act like the kid was real hurt. (Pro tip - kids don't get the kinds of soft tissue injuries that adults and especially the elderly can get.)

So my friend does some extra negotiating, and gets most of the settlement money paid to the kid. His client doesn't realize until after the papers were signed that most of "his" money was going to sit in the courts registry and go to his kid when he turns 18. He got angry, and my friend was like, "I thought that's what you wanted, I got a lot of money for your kids injuries."


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Planning With The Enemy

Family lawyer here- associate so I don't get to pick my clients yet. I had one where both parents sucked (heroin addicts). I had Mom. But didn't want either parent to end up with custody. DFCS had been called but had deemed it not severe enough to warrant removing the child. So I ended up calling another lawyer and strategizing with her to represent the grandparents so they could intervene for custody. It worked, child is with grandma and doing much better! Parents are still addicts


If There Is A God They'll Sort This Out

A serial killer murdered a locally famous man in 2017. This victim owned a restaurant and was very popular in the city. He was a good human being.

About 6 months after his murder a lady comes in claiming his house was hers. Back track about 20 years...the client and the victim bought a piece of property together. They are both on the title. They split up and she leaves a property that is literally falling apart. The property was close to being condemned. The victim hasn't had contact with my client in 15 years. He did all the work on the house and paid off the mortgage.

The victims kids are suing my client for half the house. If there is a God, they would get all of it.

In short...a house she had nothing to do with, that is worth 600k might be Hers because a serial killer murdered the owner. She is a horrible person. I want To quit the firm over this case.


The Opposite Of Something Bad Is Good? Or Good Is Bad?

Not quite, but I did a trial where I won and the defendant came up after the guilty verdict and told me I did a great job and he thought I was excellent in trial. It was tough because sometimes you want the defendant to be mad at you to make it easier to send them to jail. This was honestly a guy who was taking responsibility for his actions.

His mother was present.

So it left me feeling weird.


The Feeling Keeps Coming

Social Security Disability attorney here. I've had this feeling more than once:

  1. representing a guy who was a registered sex offender. He was in his 50s when convicted; victim was under 14. He was denied disability. He was always nice and courteous but I just despised every second in his presence.
  2. Clients who lie to me (or the judge), particularly about drug use. I've got your medical records. I can see all your blood tests and urine tests. I can see what you've admitted to your doctor. If you're not going to tell the truth—to your own lawyer—how am I supposed to help you?

P.S. 99% of the people i represent probably deserve disability. We are all 1 medical problem away from never working again; never enjoying life again. Be kind to one another and don't take your health for granted.


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