What's the most money you've lost?

[Robert Mugabe]

So far since last year. Lost 10 grand loaning it to somebody who had neither the ability or now it seems the inclination to pay it back. Phone has gone quiet. Didn't want to lend it to her, but she guilt tripped me, saying she would pay it back within a month.
Lost about 30 grand selling mastercard last fall. Learnt not to "play the market". Investments like mastercard shouldn't be touched.

 

[RichardG2020]

North of $1.5M. The lawyer got greedy. As one of the investment group and not acting in his official role as a lawyer we weren't able to get anything back.
Total take was over $16M.
He did 12 sentences concurrently of 3.5 years and was out in 2.5 for good behavior from minimum security.
If you went into a bank and threatened you had a gun you would get more.
He's a minister somewhere in the Far East now.

White collar crime is lucrative. When you weigh the risk vs. the potential return, a lot of people see it as an easy way to make money. Since the crimes aren’t violent in nature, our judicial system tends to dole out meaningless slaps on the wrist especially for first time offenders that show remorse and have the potential to improve their lives.

 

[Grimnul]

Way back in the day I used to play Magic: the Gathering. I was playing not too long after the very first releases, I had a black lotus, and alpha mox ruby, bunch of other stuff. My collection was stolen. What I had back then, knowing the value of some of the cards today, would probably be worth at least 100k today. On the plus side, I did manage to sell what was left of my collection for 5k a few years ago, so it wasn’t a complete loss. Still sucks, though. I’m 90% sure I know who did it, but I couldn’t prove it at the time and he’s dead now so I guess I got the last laugh.

Also lent 1k to a friend of mine to help her get out of an abusive relationship. Guy beat her up pretty bad, sent her to the hospital. She had to get away from him quick, but the Rogers account and a bunch of other stuff was in her name and she was responsible for paying them off and needed money or her phone was going to be shut off, which would make finding a new place and getting a job impossible (she was let go because she missed a week of work due to being in the hospital). She then proceeded to spend all the money she got from her new job going out partying, getting drunk and going to karaoke with her friends, all the while swearing she’d pay me back the second she was able. Kept telling me she didn’t have the cash, kept posting pics of her partying and going to events on social media. So I helped her when she was at her lowest, pulled her ass out of the fire, then She decided to duck me and spend the money she should’ve been using to pay me back on herself. We don’t talk anymore. She does occasionally try to message me when I’m going on vacation somewhere to ask if I can buy her something from wherever I’m going. I don’t respond.

 

[thirdcup]

Pickpocket in Paris €1000!

Many tourist attractions post signs that say beware of pickpockets. People who read the signs will instinctively reach to ensure their wallet is still where it should be. This shows the pickpockets which pocket has your wallet.

 

[thirdcup]

North of $1.5M. The lawyer got greedy. As one of the investment group and not acting in his official role as a lawyer we weren't able to get anything back.
Total take was over $16M.
He did 12 sentences concurrently of 3.5 years and was out in 2.5 for good behavior from minimum security.
If you went into a bank and threatened you had a gun you would get more.
He's a minister somewhere in the Far East now.

Don Corleone famously said to his sons - A lawyer with a briefcase can steal more than a hundred men with guns

 

[sp free]

I was down $800 at a blackjack table one time. I played one Hail Mary hand and half of it back, so walked with -$400.

Walked away from many plane tickets over the years. Lost about $1300 rental deposit when I had just rented a house in Singapore and got called back to work to help with a scheduling emergency.

I’m sure there are others.

 

[rhuarc29]

$4500 over the course of two years on a bad investment.
Biggest single-day loss would have been $1050 from playing poker when I was 20. My entire bankroll. But considering I had started at $100 the previous day, it wasn't as bad as it sounds. Made $950 playing the 1-2 for four hours the day before and decided I'd try my hand at the 2-5. Big mistake. Busted out in less than two hours.

 

[out4fun]

I lent a family member about 30k to start a business. I never expected to see it back. I was right.

I lent a friend having work and health troubles about $50k. I never expected to see it back. He passed away and left it for me in his will.

I never lend money with the expectation of seeing it again. Sometimes, the results are pleasantly surprising.

 

[thirdcup]

When in college a room mate asked over time for money that totaled close $2000. He repaid $1000. Then we graduated, went our separate ways. He came from the wrong side of the tracks. I have no doubt that $1000 meant much more to him than to me. He could have continued to string me along, and paid me nothing until we parted company. He was not a party animal. He did not blow the money on frivolous things.

I probably lost more money since then. But this was something I was in complete control of. I could have more easily said no, however I chose to say yes.

At the end of the last century I was involved in a litigation. Many bystanders said I came out in good shape. And there was a lot money at stake- millions. This was something I was not in complete control of. It took a lot of horse trading to settle the matter. I think this was a case of lost opportunity cost- what might have been.

George Best, the late soccer player, who passed away in 2005, famously said "I spent a lot of money on booze and birds (women), and the rest I just wasted"

 

[sp free]

In a similar vein, I heard an interview on the radio with Paddy Mitchell of the Stopwatch Gang who was out of prison and quite old at that point.

The interviewer asked him what he did with all the money, to which he replied “whisky and whores”

The interviewer followed up with “that’s a lot of whisky and whores” to which the old timer replied:

“It sure was”

 

[Smallcock]

Over $250k

 

[luvyeah]

Whatever my pussybux tally is at.

 

[thirdcup]

Whatever my pussybux tally is at.

The $ in your pussybux was spent on a service. I must presume you received value for your money (most of the time).

How is this any different from splashing out on a restaurant meal?
Or spending $ on a dentist, or a barber?

 

[Grimnul]

The $ in your pussybux was spent on a service. I must presume you received value for your money (most of the time).

How is this any different from splashing out on a restaurant meal?
Or spending $ on a dentist, or a barber?

This is how I see it. It’s like getting a massage. Just a little indulgence, something nice you do for yourself every now and then for stress relief. A lot of people go to spas, I have beautiful women come over and fuck my brains out. Same deal. Get to meet a lot of really cool ladies in the process as a bonus.

 

[richierich]

You do the math. I had bought 50,000 shares of apple in 1998 @ $0.94 USD.
In 2000 my mother needed a byheart surgery and I sold all my shares @ 4.94 USD to pay for it.
Best investment ever though. My mom is still alive.

 

[Moneyclutch]

You do the math. I had bought 50,000 shares of apple in 1998 @ $0.94 USD.
In 2000 my mother needed a byheart surgery and I sold all my shares @ 4.94 USD to pay for it.
Best investment ever though. My mom is still alive.

Glad your mom's out of the woods, but man, you win

 

[Frankfooter]

Over $250k

Ok, give us the details.

 

[Jasmina]

About a grand yeeeeears ago, I had put a paycheque in the back pocket of my jeans once, and when I went to get it, it was gone. I wasn't savvy enough in my youth to think about having the company cancel it and issue a new one. Awww well. Next to that, maybe a few hundred at the casino. I'm pretty guarded with my dough.

 

[RichardG2020]

You do the math. I had bought 50,000 shares of apple in 1998 @ $0.94 USD.
In 2000 my mother needed a byheart surgery and I sold all my shares @ 4.94 USD to pay for it.
Best investment ever though. My mom is still alive.

Worth every penny! But, it sucks that you had to pay out of pocket for that surgery. Here in Canada, it would have been covered. And you would have been extremely wealthy too.

 

[Ben19]

270grand on a failed investment with my cousin. Wasn’t his fault but he really felt bad since he convinced me to make that move. He has since made up for it I would say in other recommendations.