48. Carl Crawford – Boston Red Sox, Major League Baseball:
After tearing it up with the Tamp Bay Devils Rays from 2002-2010, Boston offered Crawford a seven-year contract worth $142,000,000. It averaged $20,285,714 per season and $125,220.46 per game.
This deal did not work out. Crawford spent two injury-plagued, underperforming years in Boston, calling the city a “toxic” environment that had sent him into a “depression” stage. He was traded to the Los Angeles Dodgers and retired after the 2016 season.