17 Lawyers Share Stories About The Cases They Won That Still Haunt Them

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Everybody loves to win.

And trial lawyers, usually hyper-competitive people, are certainly no exception to that rule.

But are there ever times when winning a case actually seems like a miscarriage of justice? When a win feels a lot more like a loss?

A couple of people have posed that question to askreddit, and the answers seem to indicate a resounding “Hell yes”:

#1. Foreclosures

I do a fair number of evictions as a result of holdovers after residential foreclosures. Often entire families show up for the hearing. It gets to be where it is almost a template: hysterical mom, stoic dad with a glint of anger in his eyes, angsty teen refusing to meet your gaze and oblivious child/toddler wondering why everyone looked so sad.

I sit down with these people and try to be as empathetic as possible. Most of the time they try to explain that they stopped paying because they lost their job or someone got sick. I nod and say I am sorry to hear that. Then I have to tell them that I represent the bank and the most time I am authorized to give them is seven days to get out or the sheriff will come knocking. Believe it or not, most people are very polite and even thank me after I sit and chat with them. That makes it even worse.

I wish I lost every one of those cases.

Conversely are the meth-heads and crazies who have tried to attack me or told me to fuck off and die in open court. I do not regret winning those cases.

#2. Archived

I worked for a corporation that gave free legal counseling. I was on the labor claims department, and “inherited” a case where this poor old lady hired a gardener to take care of her flowers and grass. When she was no longer able to pay him, she let him go, and he sued her for improper firing (it’s a common thing where I’m from). The judge ruled in favor of the gardener, and condemned the old lady to the equivalent of 2 years salary.

Well, long story short, when it was time to enforce the debt, the gardener moved to another address and did not inform my corporation. We had to do all contact in written, and because of this corporation’s archaic rules, all contact was made by post mail. I had his phone number, but I went strictly by the book and did not call him, just kept sending him notifications stating that we required his attendance to enforce the debt. After 5 unanswered notifications, I once again followed the rules and archived the case permanently.

#3. Ringer

I once won a case where a third wife of a defendant sued the children of the first wife for a diamond that she had never even seen, and had been in the family of the first wife (who had died) for supposedly 150-200 years. Old guy just hadn’t done a marital property agreement, and third wife had no sentimental attachment to the diamond.

We rightfully won, but damn if it didn’t feel unfair.

I’m pretty sure she sold it to buy herself a convertible.

Photo Credit: Pixabay/CC0

#4. .293

“Won” is a loose term, but here goes. Had a female DUI client who blew .293. She was early 20s, 5’7″, maybe 130 lbs. On the video she looked sober as a Quaker preacher. No balance problems, no slurred speech…a champ.

The case was non-defend-able due to the blow, but the State wanted a conviction and jail time because of the high BAC. We went with an open/blind plea to the judge and put on a hell of a case for Court Supervision. (In my state, CS keeps the conviction from entering on your criminal record and prevents your driver’s license from being revoked.)

She literally drank herself to death within a year. Turns out she was a raging alcoholic, which is why she was so functional with such a high BAC. Losing her license wouldn’t have kept her alive, but I wonder, often, if a more severe penalty (like jail) would have convinced her to get the help she needed.

#5. Why He Left

In undergrad, I took a law course taught by a former prominent defense attorney. Someone once asked why he left such a lucrative practice to teach and he told us this story:

There was a guy who, with his wife, had two foster children, boys around 10 or so. One of the boys got good grades, was a boy scout or something. The other boy was always in trouble in school, had been caught stealing and lying in the past. Well the troublesome kid told someone that the foster dad (an esteemed community member) had been molesting him. The foster dad swore he never touched him. With the kid’s background of lying and being in trouble it was clear he had made this up and that was the entire defense case. The boy took the stand cried as he was called a liar, the defense was definitely going to win.

Well the day before closing arguments, the prof/lawyer meets with his client and tells him he’s pretty sure they are going to win, goes over closing. Suddenly, foster dad asks if anything he tells his lawyer can be shared, the lawyer tells him it cannot. Foster dad looks at him and says “you know all those things he said I did to him? I did those things. I feel bad about it and won’t do it again, but thank you for believing me”. My prof tried to get himself removed from the case but because it was the day before closing arguments, it wasn’t allowed. He won the case.

#6. Deported

I once won a case where an international college student who was about three months away from graduating got permanently deported because he allegedly sent a threatening text message that was never found.

#7. Non-Accountability

I was only a part on our trial team (meaning I just drafted pleadings but didn’t do the “stand up” work at trial), but there is one case that really showed me I’ll never work for “the man” again.

The case basically involved a little girl with massive, massive disabilities (mind of a baby-no talking, motor skills/strength of a baby-pretty much can’t do anything on her own at all) who had been supposedly harmed by her caregiver. The caregiver worked for a state agency, and we were the firm that did all this agency’s litigation. To make a long story short, no one at this agency knew what the heck they were doing, and the actual caregiver had NO training whatsoever in dealing with children who have special needs. This was in a really remote area, and they hired the caregiver at the last minute knowing she wasn’t qualified.

The girl’s disabilities were so bad that it would honestly be hard to say whether or not she was actually harmed by the substandard care. That isn’t the worst part. The worst part was how much money all this stuff cost. The state spent nearly $100,000 modifying its facilities so the girl could get in/out easier, and use the restroom easier. We (because we had to in order to defend the case) hired all these experts on disability law, medicine, neuroscience, psychology/psychiatry, etc. I don’t know if you guys know how much experts cost, but it is routine for us to pay $30,000 or so for a report and a few hours of testimony in court (this case had at least 4 experts that testified for us). So the state spent a bunch of money before the case started trying to help the girl, then we spent a ton of money defending the case (oh did I mention we had at least 6 lawyers on the case, incl. 2 partners?).

On top of this, the girl’s family obviously had to hire lawyers to fight ours, so I’m sure they spent a lot of money too. Their representation was on a contingency fee, but they are still responsible for these sorts of costs, and they were poor as hell. I’m talking about scraping the bottom of the barrel poor. They were from a very remote area, lived in a ramshackle house, and neither parent had a job. They pretty much survived because of the government cheques that paid them to be their daughter’s home health aide. Nonetheless, they certainly incurred a TON of expenses even if their lawyers were paid on contingency.

Needless to say, we won at trial (it should have never gone to trial but that is a story for another day). I didn’t go to most days of the 2 week trial because I had to work, and I’m too junior to be trial counsel in federal court. I did, however, go to hear closing arguments and the verdict.

When I heard the verdict, the first feeling I had was one of mild relief–it is important for the firm that we win cases that we should win (like this one). I had also spent a ton of time working on this case, so I was glad that my work had an effect.

I turned to head out of the courtroom, pretty much oblivious to what was going on around me. I walked through the two sets of double doors to reach the hallway area, and the girl’s parents were outside. As I said before, they are poor, somewhat unkempt, and were somewhat abrasive because they were in a legal fight against us. I walked into the hall and these two strong, indignant folks had turned into absolute sobbing messes. The tall, broad-shouldered, goateed father was bawling in his wife’s arms, and she was doing the same. It was seriously the saddest thing I’ve ever seen in person, and I will never forget it.

I’m not saying they should have won or that they even had a good case. All I am saying is that I (and my colleagues) worked super hard on this case never really thinking about the humans on the other side. We weren’t mean or obnoxious, and we certainly did not do anything underhanded or unethical, but the result of our actions was still pretty much complete and utter destruction of these people’s lives. Now maybe they brought it upon themselves by picking a fight they couldn’t win, but it is hard for me to endorse that conclusion.

After seeing that, I decided that I would never again work for the big guy who crushes the little guy. A lot of lawyers believe in the principle of non-accountability. The idea that you aren’t accountable for the positions you advocate for, since you are only acting on behalf of the client. When I saw the real consequences of my actions (just or not), I decided I no longer believe in such fictions.

#8. “Outstanding debts”

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 favourable 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 health care 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 principal 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.

#9. “Justice is done…”

I’m a former assistant prosecutor, and I served in a large city. Never felt good when you won a case and an 18 year old (or younger) kid goes to jail. You do your job, “justice” is done, but, all the same, you can’t help but feel sorry about the circumstances that led to that point.

#10. Collection

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 re-argue for a man that smelled like he was allergic to showers. That was still a more enjoyable experience than working at that firm.

#11. Dr P.

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. You would not believe how careless, negligent, aloof and just completely irresponsible some specialist doctors can be.

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 fourth patient/victim died as a result of Dr. P sewing her uterus to her bladder. I do not have a clue how the a trained 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, hard evidence against the doctor (naturally, Dr. P denied every claim ever made against him).

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. But he emigrated to Canada and from what I hear his medical license didn’t last long there.

#12. The Note

 I 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.

#13. “It’s not always guilty v innocent.”

Public defenders “win” when they get a fair outcome. It’s not always guilty v innocent. More like, guilty and sentenced to 15 years and 5 probation vs guilty and sentenced to 6 years and 1 probation. Even if they know their client is guilty, they fight to get a fair sentence.

I know it’s classic to criticize attorneys as heartless money grubbers. But understand that public defenders handle AT LEAST 75 cases at a time, make about 45k a year, and work hard to defend those who can’t afford representation.

#14. Juno

I 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 deadbeat 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…

#15. Horrible Son

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.

#16. Patents

I do patent law. Often I think it sucks that I have defend a patent where, if the patent didn’t exist, lives could be saved for much, much cheaper (or free).

#17. Coma

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.

Sources: 1, 2

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