Lawyers are often faced with moral dilemmas and sometimes, they lean in the wrong way. Not bad poeple or even illegal decision, just decisions they regret, ethically. Here are 12 times lawyers really regretted the choices they made.
Breaking The Bank

“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 span of three 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.”
Very Difficult Circumstances

“Worked for an insurance company. A widow sued them after they denied paying the indemnification for her husband’s death. The man had hanged himself in a barn and the company denied the payment because under the law in effect back then, voluntary death 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 farmhouse. This would strongly support her claim that the death 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 into 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.
Now, there are some cases which I lost which I enjoyed losing, but that’s another story.”
Dr. Death Gets Defended

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“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) four 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 heck a doctor can unknowingly do that, but he somehow managed.
The thing is, Dr. P worked at a public hospital, which kept no, or virtually no, medical records and the conditions are terrible. It is thus incredibly hard to compile thorough 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…
Luckily, he immigrated to Canada, where I’m sure his career will not last long.”
Forgetting The Humanity

“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 they were doing, and the actual caregiver had NO training whatsoever in dealing with special needs children. 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 crappy part. The crappy 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 four 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 six lawyers on the case, including two 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 very poor. I’m talking about scraping the bottom of the barrel poor. They were from a very remote area, lived in a crappy house, and neither parent had a job. They pretty much survived because of the government checks 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 two 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 peoples’ 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 nonaccountability–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.”
Making Amends

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“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 ticked. I did it for about six 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.”
Getting The Wrong Kind Of Criminal Off

“I was defending a man who allegedly abused and assaulted 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.”
The Feel Good Attorney

“I’m a legal aid lawyer, kind of like a civil public defender, for those who are unfamiliar. I get paid a salary by a non-profit and my services are absolutely free to my clients. My cases are pretty much all either:
1. Working people who own nothing but the clothes on their back, household goods, and a low-value automobile they use to get to work who are declaring bankruptcy, almost always after serious medical issues (cancer, car wrecks, etc). Pretty much always able to fit all of their assets into the statutory exemptions and discharge all their debt with nothing to distribute in the bankruptcy estate. It’s tedious work but has the highest level of client satisfaction, and these are the kinds of cases that bankruptcy is really MEANT for: people who absolutely cannot pay off their debts.
2. People who are the victims of domestic violence who need help with family law issues. The only time I do divorce/custody/child support is when those issues arise in domestic violence cases. Usually, there is a pretty clear good guy and a pretty clear bad guy. Never sorry that I win child support and custody for a woman who has had her face bashed up by a violent lunatic.
3. Public housing tenants who are being evicted for nonsense. I don’t care how much rent they owe or how many lease provisions they’ve violated or how much weed they smoked. Preventing homelessness is pretty much always more important in my mind than whatever the landlord is whining about.
4. Other public benefits issues. I help people stay on welfare when the government is trying to kick them off. This is sometimes literally life-and-death. For example, I have an elderly and mentally incompetent client right now whose Medicaid is being miscalculated by the state, which puts him at risk of being kicked out of the nursing home and into the gutter.
I do not tolerate fraud in any of the above. If my client is being misleading or doing something funny, my retainer agreement and the rules of professional responsibility lets me/requires that I drop them. I love my job.”
Bamboozled By The Client

“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 adamant the client is guilty and this guy has generally got a really good gut feeling 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 adamant and to my eternal shame, I believed him. I took the case to the hearing and we fought it on the grounds that he wasn’t guilty.
Halfway 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 jerk 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.”
Foreclosures And Worse

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“Debt recovery litigation is the worst thing on the planet (going to court and taking houses can take it out of you).
Top three:
1. 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, he 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, he had hospital bills to pay, and his house was sold.
2. 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.
3. Also 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.
The worst thing is, there’s only so much of the above I believe was actually true because above all, I learned that most people lie and it also helps me sleep better at night.”
One Case That Changed Everything

“I had a professor who gave up practicing law literally in the middle of a case.
He was defending a man accused of assault. Basically, there was a woman who hung out outside a bar on most nights. Men would offer to take her home and she would say yes and they would go hook up. Defendant saw this happen for a week, so he approached her and asked her to go home with him. She said no and his thought process was, essentially, ‘What the-? This floozy sleeps with everyone but not me?!’ So he dragged her behind the bar and assaulted her.
My prof was an incredibly high profile defense attorney (celebrity clients, the whole 9 yards) and he knew that to win this case he could easily just parade each man from earlier that week in front of a jury and there was no way they would find beyond a reasonable doubt that he assaulted her because she had consented to everyone else. This dude was a rich guy and she was some chick who hung around bars waiting to sleep with men. But knowing this guy was going to get away with assault just because a woman slept around (a defense attorney has a duty to zealously represent his client, so not doing what would win the case would have been a professional misconduct) was so repulsive to him that he got the judge to allow him to withdraw (extremely difficult in the US when the trial date is set and about to commence), gave up his practice and became a law professor.
All these years later, he is struggling to pay his medical bills, fully supporting his ex-wife who he helped escape from a subsequent abusive relationship, putting his kids through college, and still refuses to do anything but pro bono work for the elderly. He is really amazing.”
Regret For Even A Small Thing

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“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.”
Taken By A Fraud

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“I’m a family lawyer, and it’s rare in my jurisdiction (New Zealand) for a case to be outright won or lost, as 90% of cases won’t actually make it to a final hearing. Even if they do, the final outcome in most cases involving the care of children will typically be a mixture of both parties’ positions.
That aside, the only case I that comes to mind involved a mother and her speed dealer boyfriend. I acted for the mother. She’d been the victim of ongoing domestic violence from him and had moved more than 20 times with her children; both to be with him and to get away from him. Eventually, the paternal grandmother applied for care of the children after the mother moved out of the area again. She was doing very well in her new place and caring for the kids very well, but the grandmother alleged that she’d left with the boyfriend again. Although it was knife-edge, the judge ordered that the mother could remain where she was, as the grandmother offered no good evidence the boyfriend was living in the new location and contradicted herself in cross-examination. He warned the mother that he’d had to place great reliance on her evidence and would refer her for perjury prosecution if it turned out she was lying.
Turns out she had been lying the whole time and he was living near to her new house (although no-one, including me, knew that of course). By the time that was found out, the file had been moved to the new city and the grandmother could no longer provide care. To her credit, she’d cleaned up her act considerably and the kids were accustomed to living in the new city, so there was no order for them to return. While I’m not exactly sorry I won, as the situation for the kids turned out to be quite good, it could easily have gone wrong all over again.”