What is the most money you have lost gambling in one night?
Usually I don't play for more than $50 or $100 a set. If I was playing pool all the time and was in dead stroke all the time, I would definitely play for more money. I don't play that much - with work and family - I have to work hard to get in dead stroke and it's a lot of effort.
A few years ago, a road player was after me to bet more, so I agreed to play 9 ball 10 ahead for $500. It was the only way he would play me and I really wanted to play this guy. He would only play me on his table, in his room, with his cue ball - etc. Like a dummy I agree to all this but I really thought I could beat him no matter what. He practiced on that table for two weeks and got in dead stroke. I heard he was running 3 and 4 packs.
So I show up and I got 15 minutes on the table. We're playing with an unmarked cueball and it was really light. The rails on this table were loose and everything banked super short. We post the money and we play for about two hours back and forth, neither of us up more than 2 games. I increasingly realized this guy was better than I thought and it was a tough match.
Then he gets ahead and gets on the hill in about 1/2 hour - everything was going his way. So I'm down 9 games with him breaking. he says to me "I'll let you off for $250". I said "I thought you wanted to play pool". He said - "Let's make a deal - $250". I was scratching my head.
Well, I had brought a couple thousand so I planned on playing him another set at least , but it was too good of a deal to pass up. So I paid him the $250 minus $50 he owed me from a previous match.
To this day I wonder why he let me off the hook with only one game to go. Afterward he said "getting that last game can be impossible sometimes, and I didn't want to lose $500."
Go figure. Road players are strange animals and he never asked me to play again.
$250 is the most I've ever lost. I've won $600 before in an evening.
Chris