Juan Gonzalez
Baseball players earn a fortune in comparison to other Major Leagues. Gonzalez received a record-breaking offer in 1999 from the Detroit Tigers. They wanted to pay him a staggering $140 million extension but he rejected them. This proved to be a career-defining error because he missed a massive payday.
Gonzalez’s next season was poor and his stock instantly declined. In the end, the Tigers didn’t want him and he went to Cleveland. But the Indians only paid him $10 million for a single year. This proves that athletes must be pragmatic about contract situations because things can change very quickly (via Sportscasting).