Jon Lester

Total Earnings: $34.1 million

Salary/Winnings: $33.7 million

Endorsements: $400,000

Lesters new $155 million deal with the Cubs includes a $30 million signing bonus with half paid in April (the balance is paid in installments between 2018 and 2020). Look for Lester to be a hit with Chicago companies. Nike remains his biggest sponsor.