Lawyers Share The Clients They Actually Regret Representing. Winning Isn't Everything.

You don't always get to choose how you spend your time at work. Lawyers know that all too well. Their job isn't to argue the ethics of the law, just the word of it. And sometimes they find themselves on the wrong side of their own sense of right and wrong.

Here, lawyers reveal the clients they regretted representing. Make sure to check out the sources at the bottom for even more.

1. Paying your dues.

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 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 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 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.


2. The cracks in the system.

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.


3. My job is on the vine.

I worked for a corporation that gavefree legal counseling. I was on the labor claims department, and"inherited" a case where this poor old lady hired a gardener to takecare of her flowers and grass. When she was no longer able to pay him, she lethim go, and he sued her for improper firing (it's a common thing where I'mfrom). The judge ruled in favor of the gardener, and condemned the old lady tothe equivalent of 2 years salary.

Well, long story short, when it was timeto enforce the debt, the gardener moved to another address and did not informmy corporation. We had to do all contact in written, and because of thiscorporation's archaic rules, all contact was made by post mail. Having hisphone, I went strictly by the book and did not call him, just kept sending himnotifications stating that we required his attendance to enforce the debt.After 5 unanswered notifications, I once again followed the rules and archivedthe case permanently.


4. Double indemnity.

Worked for an insurance company. A widowsued 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 becauseunder 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 claimbased on the fact that the man had some mental issues. In fact, the man hadexperienced a severe condition of amnesia in the past to the point of leavingthe house and wandering around for a few years before being found and takenback to their farm house. This would strongly support her claim that thesuicide was not voluntary (i.e., the man was not in full mental condition toactually discern what he was doing).

Anyway, we had to do our job so we dug deep in thecase. We started to talk to people around town and eventually we came acrossthe police officer who answered the call when the man was found hanging. Hetold us that a note was later found beside the body. We managed to work withthe bureaucracy and was able to get the note. (Story continues...)

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The note said something along theselines:

"My beloved wife. I hope you willforgive me, as well as X and Y [his sons]. I could not find any other option topay the creditors, but hopefully this decision of mine can help fix all thetroubles I caused you. Please, don't forget to pay Mr. Z and let him know I wasvery grateful for what he did to me. I love you all".

Well, we filed the note in the lawsuitand the Judge concluded that the man knew exactly what he was doing and had theclear intention of causing his family to receive the insurance money. The claimwas denied and after a few months someone told me that the widow lost her houseand her lands to creditors and simply vanished.

This really troubled me and I seriouslyconsidered quitting, but in the end I just terminated my agreement with thecompany and moved on to other cases.


5. Fighting against your former boss.

Prior to law school I worked for one ofthe largest debt collection firms in the country. I was in a department thatonly dealt with post-judgment executions... levying real property, propertyliens, 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 andswore to myself I would never go into the field after graduation.

I felt so bad about it that I work probono once a month at a local court to give credit advice to people being suedby collection agencies. Whenever I see that company's name in the caption, Iwork as hard as I can for that defendant. I once freehanded a 20 page motion tore-argue for a man that smelled like he was allergic toshowers. That was still a more enjoyable experience that working at that firm.


6. Playing by your own rules.

No regrets. I'm a legal aid lawyer, kindof like a civil public defender, for those who are unfamiliar. I get paid asalary by a non-profit and my services are absolutely free to my clients. Mycases 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 no reason. 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 theabove. If my client is being misleading or doing something funny, my retaineragreement and the rules of professional responsibility lets me/requires that Idrop them. I love my job.


7. Lawyers versus doctors.

I'm an attorney in South Africa...

When I first started practicing, Iworked at a firm that represented a huge international medical indemnitysociety. This meant that we exclusively defended doctors who had been sued for medicalmalpractice. You would not believe how careless,negligent, aloof and just completely irresponsible some specialist doctors canbe.

One doctor in particular, I will neverforget. I'll call him Dr P. Dr P is aspecialist Gynecologist and Obstetrician. During my two year stint at the firm, Dr P killed (orat least his gross negligence was responsible for the death of) 4 women. (Story continues...)

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The first two died because he perforatedtheir bowels during hysterectomy procedures. The third died when after hestitched the patient up so badly following a cesarean, the wound collapsed andwent septic resulting in organ failure.

The forth patient/victim died as a resultof Dr. P sewing her uterus to her bladder. I do not have a clue how the a traineddoctor can unknowingly do that, but he somehow managed...

Thing is, Dr P worked at a publichospital, which keep no, or virtually no medical records and the conditions areterrible. It is thus incredibly hard to compile thorough, hard evidenceagainst the doctor (naturally, Dr. P denied every claim ever made against him).

In all four, we defended Dr Psuccessfully with applications for absolution from the instance.

Eventually, I considered how I couldwarn people about Dr P, without breaking attorney-client confidentiality, butthere was no way.

It haunts me still that he ispracticing. But he immigrated to Canada and from what I hear his medical license didn't last long there.


8. A thankless task.

Public defenders "win" whenthey get a fair outcome. It's not always guilty v innocent. More like, guilty andsentenced to 15 years and 5 probation vs guilty and sentenced to 6 years and 1probation. Even if they know their client is guilty, they fight to get a fairsentence.

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 about45k a year, and work hard to defend those who can't affordrepresentation.


9. Patently ridiculous.

I do patent law. Often I think it sucksthat I have defend a patent that if the patent didn't exist lives could besaved for much, much cheaper (or free).


10. Working from the inside.

I do mortgage foreclosures. I had aclient that was foreclosing on a property with a remaining principal balance ofabout $600.

The owner of the property (old lady) hadrequested payoff figures to payoff the remaining balance of her mortgage. Whenshe got them in September they included money to be paid into escrow forproperty taxes due in November. She paid everything but the amount that wouldhave gone to escrow because by her reasoning (which I agreed with) if she paidoff the mortgage before November then whether the property taxes were paid wasno longer a concern of the mortgage company.

Well, my client applied some of thepayment to escrow, so instead of completely paying it off there was a remainingbalance of about $600. She thought her mortgage was paid off and didn't makeany further payments. Late fees built up, then they decided to foreclose, andlegal fees built up, until I saw the file and refused to move forward. Theywere paying me more in legal fees than they were owed! It was ridiculous. (Story continues...)

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They had a legal right to do what theydid, and to foreclose, and they kept insisting on that. I had to argue thatthat didn't mean it wasn't wrong to do it, or that any judge I broughtthis to wouldn't find a way to make sure it never went anywhere. I eventuallytalked them down and they wrote off the remaining amount due.

The whole time the woman who was beingforeclosed on was angry at me, and I couldn't tell her that I agreedwith her and was trying to make the whole thing go away. To this day I'm sureshe thinks she "beat" me.


11. Bounty collecting isn't nearly as cool as it sounds.

Debt recovery litigation is the worstthing 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..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.
  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 dead beat 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 somuch of the above I believe was actually true (because above all, I learned thatmost people lie..and it also helps me sleep better at night)


12. Sentenced to a lifetime in time-out.

I played lawyer on the playground inelementary school once. A kid had borrowed a few bucks from another kid andthen 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. Itold him that for a dollar, I'd devise us a plan to get his money back. Heagreed.

I told the loaned kid that the loaner was mad as hell and was going topunch 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 waspaid back. Never got my dollar though so that's why I regret it.


13. When tragedy becomes mundane.

I do a fair number of evictions as a result ofholdovers after residential foreclosures. Often entire families show up for thehearing. It gets to be where it is almost a template: hysterical mom, stoic dadwith a glint of anger in his eyes, angsty teen refusing to meet your gaze andoblivious child/toddler wondering why everyone looked so sad. (Story continues...)

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I sit down with these people and try tobe as empathetic as possible. Most of the time they try to explain that theystopped paying because they lost their job or someone got sick. I nod and say Iam sorry to hear that. Then I have to tell them that I represent the bank andthe most time I am authorized to give them is seven days to get out or thesheriff will come knocking. Believe it or not, most people are very polite andeven 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 people who have tried to attack me or told me how they were going to kill me in opencourt. I do not regret winning those cases.


14. Diamonds are forever.

I once won a case where a third wife ofa decedent sued the children of the first wife for a diamond that she had nevereven seen, and had been in the family of the first wife (she died, leaving thedecedent as a widower, who then held onto the diamond for the next decade) forsupposedly 150-200 years. Old guy just hadn't done a marital propertyagreement, and third wife had no sentimental attachment to the diamond. Werightfully won, but damn if it didn't feel unfair.

I'm pretty sure she sold it to buyherself a convertible.

Moral of the story:Have a marital property agreement (pre-nup or post-nup) and do your EstatePlanning. Especially if you've had kids and/or multiple marriages.


15. Technicalities don't count as lies right?

Lawyers get a bad rap. Sure, there aresome bad apples, but the same is true for priest, doctors and teachers. Forexample, criminal defense attorneys are literally the guardians of ourconstitutional rights - the last line of defense between the state and thecitizens. If you believe in the justice system, then you believe everyone, eventhose assumed guilty, is entitled to a fair trial. By ensuring that even themost hated get their day in court - they attempt to ensure that the rest of uswill too.

AND most criminal defense attorneys / prosecutorsdon't actually make that much money, especially when adjusted for hours worked.There are a handful of guys in the country that make insane money, but the restare solidly working / middle class.

Lastly, most lawyers don't flat out lie.Their job is to make the other side prove its case. Like most people in anargument, they present the facts and tell the story in a way most favorable totheir side. It's up to the judge or jury, as an allegedly impartial decider, towade through both sides story and decide what they believe. Not a perfect systemby any means, but the best one invented to date.


16. Talk about a bittersweet ending...

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. (Story continues...)

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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, feeling as though I let one of the world's most beautiful human's down in the dead father.


17. 'The saddest thing I've ever seen.'

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

The case basically involved a littlegirl with massive, massive disabilities (mind of a baby-no talking, motorskills/strength of a baby-pretty much can't do anything on her own at all) whohad been supposedly harmed by her caregiver. The caregiver worked for a stateagency, and we were the firm that did all this agency's litigation. To make along story short, no one at this agency knew what the heck they were doing, andthe 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 thelast minute knowing she wasn't qualified.

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

On top of this, the girl's familyobviously had to hire lawyers to fight ours, so I'm sure they spent a lot ofmoney too. Their representation was on a contingency fee, but they are stillresponsible for these sorts of costs, and they were poor as hell. I'm talkingabout scraping the bottom of the barrel poor. They were from a very remotearea, lived in a ramshackle house, and neither parent had a job. They prettymuch survived because of the government cheques that paid them to be theirdaughter's home health aide. Nonetheless, they certainly incurred a TON ofexpenses even if their lawyers were paid on contingency.

Needless to say, we won at trial (itshould have never gone to trial but that is a story for another day). I didn'tgo to most days of the 2 week trial because I had to work, and I'm too juniorto be trial counsel in federal court. I did, however, go to hear closingarguments and the verdict.

When I heard the verdict, the firstfeeling I had was one of mild relief--it is important for the firm that we wincases that we should win (like this one). I had also spent a ton of timeworking 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 twosets of double doors to reach the hallway area, and the girl's parents wereoutside. As I said before, they are poor, somewhat unkept, and were somewhatabrasive because they were in a legal fight against us. I walked into the halland these two strong, indignant folks had turned into absolute sobbing messes.The tall, broad-shouldered, goateed father was bawling in his wife's arms, andshe was doing the same. It was seriously the saddest thing I've ever seen inperson, and I will never forget it.

I'm not saying they should have won orthat 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 theother side. We weren't mean or obnoxious, and we certainly did not do anythingunderhanded or unethical, but the result of our actions was still pretty muchcomplete and utter destruction of these peoples' lives. Now maybe they broughtit upon themselves by picking a fight they couldn't win, but it is hard for meto endorse that conclusion.

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


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Your local police officer likely doesn't care about jaywalking or the fact that you went five miles over the speed limit unless you give him a reason to, as we learned when Redditor Takdel asked police officers: "What stupid law have you enforced just because someone was an a-hole?"

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