11. Joe DiMaggio
MLB stars rarely engage in contract holdouts because they receive guaranteed contracts. That’s also why great players stay with bad teams because they’re making money. However, DiMaggio famously had a financial spat with the Yankees. He demanded a $40,000 salary but the franchise wasn’t willing to sanction that. They ended up at loggerheads with each other.
DiMaggio overestimated his star power because the Yankees didn’t back down. In the end, they gave him a $25,000 deal. This was much lower than the amount that he demanded. However, if he didn’t play the team wouldn’t pay him so he was in a no-win situation. Sometimes front offices hold all of the cards and the player must bend the knee (via PBS).