Chicago Cubs: Who will be making the most money in 2020?

Chicago Cubs: Time goes by fast, especially when you have fun.

Very late at night on December 10, 2014, the Chicago Cubs won the Jon Lester sweepstakes. A six-year, $155 million deal was agreed upon between the Cubs and Lester, which would begin what has become one of the team’s greatest free agent signings ever.

After two All Star appearances, NLCS MVP honors and of course a World Series championship, the clock is winding down on old Jon. He has one more guaranteed year left on his deal for 2020, in which he will make $20 million. That is $15 million in base salary and $5 million in signing bonus money. It will be the smallest annual salary for him since his first year in 2015.

Note that 2021 has a $25 million vested option with a $10 million buyout. Lester would have to accumulate 400 innings between 2019 and 2020 or pitch 200 innings in 2020. With the way things are trending both with age and declining performance, Lester’s last year as a Cubs is going to be 2020.

Worth every penny.