Cubs, Yankees To Heavily Pursue Jon Lester This Winter?

Posted on Aug 20 2014 - 4:23pm by Johnny Feulner
Jon Lester was traded to Oakland at the deadline and will be a free agent after the season - Mandatory Credit: Ezra Shaw/Getty Images via ESPN.com

Jon Lester was traded to Oakland at the deadline and will be a free agent after the season – Mandatory Credit: Ezra Shaw/Getty Images via ESPN.com

Jon Lester will be one of the biggest pitchers on the market at season’s end, and he’s expected to draw a number of suitors.

While his current team, the Oakland Athletics, could certainly offer him a generous contract to stay, their general manager, Billy Beane, has never been one to gift-wrap those kind of deals. And there’s growing speculation Lester would re-sign with the Boston Red Sox.

Lester, who spent his entire nine-year career with Boston before being dealt, said it’s “definitely a place” he would go, per John Tomase of the Boston Herald. Yet, could he wind up somewhere else other than these two clubs? Possibly, a “darker side.”

According to CBS Sports’ Jon Heyman, he believes the Chicago Cubs and the New York Yankees – as well as others – are the likeliest possible destinations for Lester, and that the Red Sox are in fact long shots to retrieve their beloved lefty ace.

Heyman goes on to write that the Yankees have been fond of Lester’s competitive edge, and that New York would “surely” make a pitch to him. And he says the Cubs will be interested, given Chicago’s current president of baseball operations, Theo Epstein, and general manager Jed Hoyer, “absolutely love” Lester from their time in Boston.

Lester, 30, has said that he’s going to sign with a team that makes him and his family happy, rather than to the highest bidder, per Tomase. Most would assume that implies reuniting with Boston, but, truth of the matter is, it’s hard to believe someone in baseball nowadays who says they’ll take less money to be comfortable.

Obviously, it’s a safe bet to predict the Yankees will enter the Lester sweepstakes; that’s probably a given. And while everyone states a situation like that would never happen, just ask Jacoby Ellsbury and Johnny Damon.

In 25 starts between Boston and Oakland this season, Lester is 13-8 with a 2.58 ERA and has 174 strikeouts.