8. Alex Rodriguez – Texas Rangers, Major League Baseball:
Rodriguez signed with Texas for 10 years $252,000,000 before the 2001 season in his first appearance of two on the list of richest sports contracts. At the time, it was the biggest contract in MLB history by a large margin. It outpaced every other MLB contract by $63 million in fact. The deal averaged $25,200,000 a season and $155,555.56 per game.
It wasn’t worth it for the Texas Rangers. Rodriguez was gone from the team by 2003, heading to sign another huge long-term deal with the Yankees.