I guess this one wouldn't be someone who couldn't retire, but it does fit the mold.
When I was in my 20s I worked with a guy in his late 20s. Solid, white collar worker, not great with money, but not incredibly stupid. Anyway, he had a friend that liked to gamble. The guy ends up on television (BTW, working a late night in the office, we are watching this guy on TV) in a poker tournament. $1000 buy in, no limit Texas Hold'Em, with something like 10,000 entrants. One of those tournaments that basically requires you to play in twelve hour shifts over more than 3 days, sleep optional.
The final day was televised.
My coworker's friend makes it to the final table, despite being pretty drunk. My coworker gets the OK to leave work early and race down to Atlantic City to catch the rest of the action. I give him my personal cabbie hookup, who is very fast and safe. He's in AC from Connecticut in 2 hours to watch his friend.
At work, the interest in it continues. I have the feed up in the background while I'm working, and I'm listening to the audio.
-At one point my coworker's friend is chip leader.
-Slowly, the other players go bust and collect their final table prize money. The amounts keep going up. Top prize is close to a million dollars.
-It's down to 3 players left.
-It's down to 2. He is still chip leader. As the favorite in the hand, he puts the other guy all in and gets sucked out hard. The other guy lives to fight another day.
-Slowly, my coworker's friend starts going on tilt, chasing the scenario of putting the other guy all in again, making several bad bets in the process. He gives up his chip lead and becomes the underdog. His stack slowly whittles down until he is put all in as the underdog, and he finishes 2nd.
-He wins about $600,000.
After withholding, he winds up with under $400,000.
The next day, my coworker tells me:
-His friend owed various people $200,000 in gambling debts.
-He spent about $175,000 that night partying. Apparently, he bought everyone who was around and watching the poker tournament expensive mixed drinks, bought a very expensive bottle, and paid to do VIP something at some club down there. And of course he upgraded his hotel accommodations and extended his stay for one more night, which makes perfect sense, because who could sleep in a regular hotel after winning that much money?
So, basically, the guy won over a half million dollars, and literally the next morning walked away with less than $25,000.