Jon Lester: $34.1 Million – Baseball
When Lester signed his $155 million deal with the Cubs and said good-bye to Boston, he left behind sponsorship deals with New England Ford, Verizon Wireless and People’s United Bank. Of course it is expected that other companies will quickly pick him up, and he still has his big sponsor Nike. Lester also received a $30 million signing bonus, getting half in April 2015 and the rest via installments between 2018 and 2020. Pretty nice.