16. Prince Fielder – Detroit Tigers, Major League Baseball:
In January 2012, former Milwaukee star Fielder signed with Detroit for 9 years and $214,000,000. At the time, it was the largest contract in the history of the team when it topped surpassing Miguel Cabrera’s 8-year, $185.3 million deal. It paid Fielder an average of $23,777,777 a season and $146,776.40 per game.
He was later traded to the Texas Rangers in November 2013. He retired in 2016 after sustaining serious neck injuries. It’s tough to call his contract a bad deal because injuries sapped him of his skills, but clearly, it didn’t work out for the Tigers.