After signing with the Chicago Cubs prior to the 2015 season, veteran southpaw Jon Lester helped turn around the franchise and lead them to their first World Series in 108 years just one year later. To call the first four years of his time in a Cubs uniform a success really doesn’t do it justice.
On the North Side, Lester carries a 61-31 record with a 3.26 ERA into 2019. He tied a career-high with 19 wins while finishing as the runner-up in NL Cy Young voting three years ago and narrowly missed that mark in 2018, winning 18 contests for Chicago.