I was playing a progression on a $25 table.
Years ago, on full tilt, losing $5k..placed the last $3k of my bankroll in blackjack
Dealt a natural blackjack and checked out for the weekend and drove home.
(I am sure EvenBob would have been foaming at the mouth watching this, then utterly disappointed in the outcome)
Similar situation except I was down around $1000 for the trip plus $400 for the session. Had to leave to catch my flight and put remaining $600 down, dealt a blackjack. It was a pitch game and I slammed the cards down on the table, accidentally bending them. The dealer was not very pleased, even though I had a $5 bet out for her as well. (Probably not pleased that it was such a small amount!)
She'd dragged her feet after graduating, then got pregnant and went into full mommy-mode. My buddy kept saying things like "I can't wait until she starts working - we'll have so much more money!" and I kept saying things like "yeah, only 5 more years until kindergarden!" So we made the bet. We both agreed not to tell his wife, and I do think her wrath would have outweighed the value of the money if she knew we bet on that, but I still kind of wonder if he told her at some point.
Ah, I see now. At first, I thought she had been aware of the wager...haha
All of us who read the forums will not make a bet unless we know the numbers and probabilities, unless it is for fun (such as a $5 BJ table to pass the time, entertainment, etc).
Now hold up - I think I speak for a lot of this board when I say that even if I'm losing, I'd like to know how much I'm losing.
(Although it's probably when I started playing single-deck blackjack on Bovada, mostly at $25, occasionally pressing my luck to $50 or $100 when immediately winning, and wound up losing $4000 in one drunken night after about a quarter million in handle. Not a night I'm proud of.)
I once had a $10 bet on an 8 ball game with exactly $3 in my pocket. It was on Padre Island in a bad news bar. Walked out with $170. Slept on the beach that night, but kept two of the metal tent pegs next to me.
What was your most significant "gamble" in terms of stakes?
Back in the day when I was sleeping around with different women, I frequently had unprotected sex.
In hindsight: a foolish gamble, with pretty much the highest of all possible stakes.