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Source: Cubs, Jon Lester agree to 6-year, $155 million deal

12.10.14 at 1:36 am ET
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Jon Lester's Red Sox career is now in the rearview mirror. (Jim Rogash/Getty Images)

Jon Lester‘s Red Sox career now is in the rearview mirror. (Jim Rogash/Getty Images)

SAN DIEGO — Almost a year after his proclaimed interest in returning to the Red Sox on a hometown discount, left-hander Jon Lester rejected his former team’s free agent overtures and instead chose to make his baseball home in Chicago with the Cubs, according to an industry source.

Lester agreed to a six-year, $155 million deal, the largest average annual value ($25.83 million) ever given to a pitcher on a multi-year deal in free agency. His deal with the Cubs includes a vesting option for a seventh year. The Sox’ final offer, according to another industry source, was for a six-year, $135 million deal with no seventh-year vesting option.

Lester’s decision followed a weeks-long process of visits with interested teams and two full days at the Major League Baseball winter meetings in which much of the industry’s activity seemed to depend upon his decision.

“You just wait for the white smoke,” Cubs manager Joe Maddon joked on Tuesday afternoon of the wait for Lester’s choice between his team, the Red Sox, Giants and Dodgers. “This is a guy when the game is really big he was always at his best. To possibly get this opportunity to work with him for the first time is very exciting. … [You] can’t have any more respect for a baseball player than we do for him now. For us to be able to pull this off it would be pretty outstanding.”

In choosing to sign with the Cubs, Lester joins a front office with whom he has a great deal of familiarity. Cubs president of baseball operations Theo Epstein, general manager Jed Hoyer and assistant GM Jason McLeod all have close relationships with the pitcher after spending years with him in the Red Sox system.

A case can be made that the fact Lester chose that group rather than a Sox organization with whom he spent the first 12 years of his career represented a particularly painful dagger for Boston. Lester was the first player drafted under the current Sox owners in 2002 and contributed to two World Series titles, foremost with a dominant performance for the ages in the 2013 postseason.

Lester had made no secret of his desire to return to the Red Sox, stating in no uncertain terms prior to the 2014 season that he would take less than full market value in hopes of remaining with the Sox for his entire career. But when the Sox made an initial four-year, $70 million offer to Lester in spring training, the pitcher and club saw insufficient common ground to continue talks during the season, and Lester didn’t re-open the door to in-season negotiations.

Still, even after the team traded Lester (and Jonny Gomes) to the A’s at the trade deadline for Yoenis Cespedes, the Sox remained adamant that they’d make a run at the pitcher when he arrived at free agency after the season following a 16-11 season in which he had a career-best 2.46 ERA and 220 strikeouts in 219 2/3 innings. That is precisely what they did, with team ownership meeting with him in the Atlanta area in November and principal owner John Henry traveling back to meet with the pitcher one-on-one again last week. The team showed a willingness to go to six years — the longest guarantee ever made under the Henry ownership group.

But ultimately, Lester, 30, opted to be a part of Chicago’s effort to end its 106-year championship drought. The Red Sox, who have two holes in their rotation, must now focus their attentions elsewhere as they pursue a top-of-the-rotation option for 2015 and beyond.

Read More: 2014 winter meetings, cubs, Jon Lester,
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