I said no. To win the bet, win the games. To keep the winnings, stop while he can still pay.
I’m not skilled enough at ping pong to play for $2k per game. Yet tonight I played ping-pong for $2k per game.
Here’s how:
He asked, “Ping pong?”
I said, “Sure. $100 per game?”
His eyes lit up. “Sure.”
We agreed: game to 21, 5 serves per person, serves must be cross-court.
I won the first game. We played again. I won. A third time: I won.
He said, “Double?”
I asked, “What do you mean?”
He said, “$200 per game.”
I said, “I’m up $300. You want to play for $200 per game?”
He said yes.
I won.
He said, “$500? I need to clear this out.”
We shook hands.
I won.
“$1,000?”
I won.
“$2,000?”
I won.
So now I’m up $4,000. And the biggest danger in this spot is the guy not paying. Because I’d pay a $4,000 debt if I had one. I only make bets I’ll cover. So if he doesn’t pay his debt, he was free-rolling me the whole time. (“Free-rolling” is when you have the ability to win but no ability to lose. If he would collect upon a victory but not pay upon a loss, he’s free-rolling me for the bet.)
I also 1) don’t want him to feel shitty, and 2) don’t want him to stiff me.
So when he says he wants to play for $4k, I know he’s steaming. I know he’s fuming. He’s physically pacing at the base of the ping pong table like Chris Rock on stage. And I don’t know if he’s someone who will actually pay his debt. If he is, we can play for more later. If he isn’t, I don’t want to gamble anymore.
The game is no longer ping pong. The game is: will this guy pay off an $8k debt? If not, I’m taking my ping-pong ball and going home.
Julian Wise 