One of the regulars at the Board Room was Jess, a very bad bumper pool player who constantly challenged me to five dollar games, never won a single game, and always raised the stakes.
Now there were perhaps eight or ten regulars that I would take two or three dollars from once in a while, or even ten or fifteen dollars, but Jess was a different case. I doubt that I ever won less than a hundred dollars from him in a session, and I didn't feel all that good about it. He didn't seem to have any money problems, but I was not a pool hustler - I had a job, I just enjoyed playing, and the money was a way to keep score.
Finally I reached the end of my rope. He came in one night, ordered a drink, turned to me, and said, "Ready, Donnie?"
"Jess, I don't want to play you any more."
"What? Why not?"
"I don't feel good about it. It's too much money, and you're a nice guy but a terrible bumper pool player."
"I'm not that bad!"
"Jess, no offense, but you're hopeless. You're never gonna win a game against me. I don't care how much money you have, I'm not happy taking it from you."
"Come on, Donnie, I'm really not that bad."
I thought for a couple of minutes. "Alright, Jess, I have a deal for you. We'll play one game for fifty dollars. I'll start with my first ball in the middle of the bumpers and I'll play one-handed. You'll play your normal game. If I win, you give up bumper pool."
"That's crazy, Donnie. You can't win that game."
"That's my offer."
We played, he lost, and in fact he still had three balls on the table when I sunk my final ball.
He gave me the fifty, shook his head, and said, "I never would have believed it. You're right. I am that bad."
He kept his word and never played bumper pool again - or at least he never played again in the Board Room.