This thread just unlocked an old memory of a comic in one of the first issues of the Simpsons magazine in like 1992?
Homer is playing golf and Mr Burns shows up. Mr Burns plays against Homer and suggests they wager "5". Home agrees.
Then Homer starts panicking to himself because Mr Burns is rich and he doesn't know what 5 means. 5 million? 5 thousand? How much do rich people bet on casual golf games?
So he kills himself trying to win the game because he can't afford to lose. Then at the end he wins and Mr Burns gives him a 5 dollar bill.
(Found mention of it on the intarwebz
https://simpsonswiki.com/wiki/Par_for_the_Curse)