Jon Lester finally makes decision, signs with Chicago Cubs

No other player has handcuffed both the free agent and trade markets as much as Jon Lester has over the past few weeks, but the left-hander has finally reached a decision about his future. Late Tuesday night, Lester reportedly came to terms with the Chicago Cubs on a six-year deal worth $155 million.

The deal with Chicago also includes an option for a seventh year, valued at $15 million.

The pursuit of the veteran starter has occupied discussion for much of the offseason, particularly as things appeared to heat up over the past week with the Winter Meetings approaching. A once broader group of teams was narrowed down to four: the Los Angeles Dodgers, San Francisco Giants, Cubs and Red Sox. The rumored favorite jumped between the latter three throughout the day Monday and Tuesday.

By Tuesday evening both the Giants and Dodgers had officially been ruled out. Los Angeles never appeared to be as invested as the other three. Multiple sources reported that Giants assistant GM Dan Evans informed them that Lester called the team’s front office himself to let them know that he wouldn’t be coming to San Francisco. The Giants didn’t look like they’d be in the mix early on, but once the team lost Pablo Sandoval to Boston they shifted gears – potentially using that payroll to help balance a significant addition to the rotation instead. The team will likely direct their attention back to that hole at third base, as well as other needs.

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All along this figured to be a race between the Cubs and Red Sox. The two organizations made the most sense, for a variety of reasons.

Up until he was traded this past July, Lester had spent his entire career with the Red Sox organization. He’d been developed in their minor league system, threw a no-hitter with them, won two World Series, and completely endeared himself to a significant portion of the team’s fan base. Boston never should have allowed things to even get to this point, unable to complete an extension with Lester this past spring. Boston’s approach was unexpected and their initial offer was viewed as an embarrassment. The two sides never came close to an agreement, ultimately leading to the deal at the trade deadline that sent Lester to Oakland.

There’s a familiarity and a history between Lester and the Red Sox, one that would be difficult to walk away.

Some of that same comfort applies to Chicago, of course, given some of the names that populate the club’s front office. Theo Epstein was Boston’s GM early on in Lester’s career. The two maintain a strong relationship, as Lester does with former teammate Ryan Dempster – who recently retired to take a position with the team’s operations department.

With Lester joining the Cubs, he’ll be asked to step in and become the de facto ace of what is still an inexperienced rotation. Jake Arrieta‘s emergence this past season makes him appear to be a strong second starter with Jason Hammel, Edwin Jackson, Travis Wood, and Kyle Hendricks also in the mix.