Ranking the 10 best Chicago Cubs moves during the Theo Epstein era

1. Signing Jon Lester

In the offseason prior to the 2015 season, the Cubs were three years into a rebuild and looking to step back into contention. And Epstein made a splash that was a clear message to the rest of the league. Lester, who was the second-best pitcher on the market after Max Scherzer, signed with Chicago for a six-year, $155 million deal.

Lester was already a grizzled veteran with two World Series rings to his name. He was coming off seven straight seasons of making 30+ starts, a streak he continued for five of his six years in Chicago. He was a bulldog inning eater who gave the team a dominant rotation when Arrieta and Hendricks took major steps forward. The fact that Lester looked more like the number 2 pitcher in 2015 is certainly a testament to Arrieta's monstrous season than an indictment of Lester's abilities.

Lester returned the favor in 2016 though, when he tossed 202 innings with a 2.44 ERA, the second lowest in baseball behind Hendricks. The southpaw threw a total of 1003.2 innings in a Cubs uniform over six seasons, giving the team an immovable rock in the rotation who gave it his all every start. That kind of consistency is hard to come by given the number of pitching injuries that plague the league today, but Lester was seemingly immune to such setbacks.

Given that Epstein drafted Lester in Boston, rumors linked the big lefty to Chicago well before he hit free agency. It was a perfect match and one Epstein used to position the Cubs for success for the rest of the 2010's.