Jon Lester goes to Cubs for $155 million over six years

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As FOXSports.com’s Ken Rosenthal first reported, Jon Lester has opted to join the Cubs. Yahoo Sports’ Jeff Passan confirms that it’s a six-year, $155 million deal. The Red Sox were offering $135 million for six years.

Lester also had offers from the Giants and Dodgers before reportedly narrowing to two finalists earlier Tuesday. According to Passan, the Giants were offering six years and $150 million, with seven years and $168 million also possibly in play.

That the Red Sox were still in the process so late despite the lesser offer suggests that Lester would have returned to Boston all things being equal and that he nearly did anyway. Still, there had to be some divided loyalties, given former Red Sox GM Theo Epstein’s presence in the Cubs front office and the fact that Boston’s earlier offers prior to him becoming a free agent were very nearly insulting.

Chicago likely is a better situation for Lester, given that the club is oozing with young talent, and the Cubs clearly wanted him more. He’ll join an improved rotation also set to include Jason Hammel, Jake Arrieta and probably Kyle Hendricks. The Cubs could acquire another starter or leave the fifth spot open for Tsuyoshi Wada, Travis Wood, Edwin Jackson, Dan Straily, Felix Doubront or Jacob Turner.

One other interesting call is whether the Cubs will now bring in David Ross, who worked so well with Lester in Boston. The Red Sox were expected to re-sign Ross if Lester came back, and he made plenty of sense for the Cubs a day ago. Now, though, the Cubs have Miguel Montero, freshly acquired from the Diamondbacks, as their new starting catcher, and last year’s starter, Welington Castillo, still on the roster. The Cubs could trade Castillo and open up a spot for Ross, but using a personal catcher for Lester would negate some of Montero’s offensive value. Ideally, the Cubs would platoon the lefty swinging Montero and Castillo or another right-handed catcher based on who their facing. If Lester has a personal catcher, that advantage would be lost.

The Red Sox will now move on to plan B, though whether that includes a run at Max Scherzer or James Shields is unclear. They have no chance of getting Scherzer without a major upgrade on what they were offering Lester. They might instead explore trades for Jordan Zimmermann and Johnny Cueto. Cole Hamels is a frequent topic of conversation, but nothing is going to happen there unless Ruben Amaro lowers his asking price.

Boston will also look to the next tier of starters in trades and free agency. Rosenthal reported that the Red Sox and Marlins were both pursuing Arizona’s Wade Miley. Other free agents of interest to Boston could include Brandon McCarthy and Ervin Santana.