14. David Price – Boston Red Sox, Major League Baseball:
Price signed with the Red Sox for 7 years and $217,000,000 in late 2015. It was a Boston record. The contract topped Kershaw’s aforementioned record for single-season value at $31,000,000 and averaged $191,358.02 per game.
He went through several nagging injuries during the 2017 season but bounced back strong in 2018. There, Price started the Red Sox’ World Series-clinching Game 5, earning the American League Comeback Player of the Year award. It’s safe to say this huge deal was a good one.