MLB Hot Stove 2014: Jon Lester Chooses The Chicago Cubs

Matt Zylbert discusses the Chicago Cubs recent free agent signing of Jon Lester. RotoBaller has you covered on all of the hot stove and fantasy baseball news this offseason.

After an intensely-contested long process, it came down to two teams: his previous club whom he won two World Series Championships with, or an interestingly resurgent one that has grabbed the attention of everyone in baseball this offseason despite five consecutive fifth-place finishes in their own division.

In the end, stud left-hander Jon Lester went with the not-so obvious choice, selecting another historic baseball city instead by joining the Cubs. In addition, he’ll be re-uniting with former Red Sox GM Theo Epstein, who was with Lester on the 2007 Championship squad in Boston. Epstein is also responsible for engineering the ’04 roster that won the franchise’s first title since 1918.

In this instance, Lester and Epstein will seek to nab the Cubs’ first World Series title since 1908.

The three-time All-Star comes to Chicago following yet another fantastic campaign, one in which that also saw him go to another team for the first time in his career. Across 32 starts with the Red Sox and Athletics, Lester finished 16-11 with an outstanding 2.46 ERA and 1.10 WHIP -- both career-bests -- while racking up 220 K in a career-high 219.2 IP. The nine-year veteran undoubtedly will slide in at the top of the rotation just above upstart right-hander Jake Arrieta, providing the Cubs with one of the best aces in the game today.

The North Siders haven’t won more than 75 games since 2008, which was the year they last made the playoffs, but appear poised to finally shed the laughingstock reputation that has been attached to the club over the last half-decade, if not longer. The Cubs possess a plethora of highly-touted young emerging talent that are reaching their Major League destination at the same exact time, making them a very dangerous and dynamic club entering the 2015 campaign.

In other Winter Meeting news, Chicago also acquired Miguel Montero from the Dbacks for two low-level prospects. Montero had been with Arizona for all nine of his years in the big leagues, and despite seeing his production drop off in the past couple of seasons, he immediately provides the Cubbies with an upgrade at catcher.