Sponsorships/Winnings: $33.7m Endorsements: $400k Another Chicago-based sportsman who is earning top dollar is Jon Lester, starting pitcher for the Chicago Cubs. Although he may be earning a paltry $400k from endorsements (I mean, really, why even bother getting out of bed?), he signed with the Cubs on a six-year-deal worth a staggering $155m. The Cubs haven't won a World Series in over a century, and are investing heavily in Lester - who has two championships to his name, in 2007 and 2013 with the Boston Red Sox - to be the man who helps them put that record right. If that happens, that $400k in endorsements might just take a considerable leap.