When the Cubs decided to sign Jon Lester back in the offseason of 2014, they had an idea of the type of pitcher they were getting. Lester was about to turn 30 years old and brought with him an already impressive resume from the Boston Red Sox. It was an easy decision for Theo Epstein.
Epstein grew with Lester. He had watched Lester dominate year in and year out for the Red Sox. When Epstein came to the Cubs, it became clockwork, as Lester was wooed to the Windy City on a mega six-year contract, totaling $155 million.