Will Jon Lester Re-Sign With Red Sox In 2015? Pitcher Favorites Tweets About Return To Boston

Just because the Red Sox traded starting pitcher Jon Lester to the Oakland Athletics on Thursday doesn’t mean that he won’t be playing for Boston in 2015.

The Red Sox sent Lester and outfielder Jonny Gomes to the A’s in exchange for slugger Yoenis Cespedes, ESPN reports. Upon learning of the trade, Lester, a hometown favorite who was a major contributor to Boston’s World Series teams in 2007 and 2013, favorited a pair of tweets which discussed the possibility that he’d re-sign with the Red Sox for the 2015 season, Barstool Sports notes.

Lester may have just been grateful for the praise, but a return to Boston is a real possibility this offseason. The 30-year-old will be a free agent as soon as the season ends, and he made it clear throughout contract negotiations that his preference would be to return to the Red Sox.

With a record of 48-60, the Red Sox are likely out of playoff contention this season. By trading Lester, General Manager Ben Cherington was able to acquire a serviceable power hitter rather than lose his ace without compensation in free agency. Furthermore, given Lester’s loyalty to the Fenway Park faithful, the trade is a “risk worth taking,” according to an MLB executive who has spoken to Boston team officials.

“It makes way too much sense for them to trade Lester. They have tried to sign him, and they obviously are not going to do that in the short term here. So if they want to sign him in the offseason, the only risk they are running is that he goes somewhere else, gets comfortable and decides he wants to stay there rather than testing free agency,” the executive told the New York Post.

“It is not a negligible risk, but it is a risk worth taking. Because think of the win-win – they can get the prospects for Lester and still have him in 2015 and beyond. Plus, it might seem a small thing, but if they sign him in the offseason as a free agent, they would not get the draft picks if he were to sign somewhere else. So this is like doing better than those draft picks and – if they are able – also getting Lester back,” the source added.

For Oakland, the addition of Lester to an already impressive starting rotation solidifies the A’s as a top contender for the 2014 World Series. Meanwhile, Boston also shed fellow starters Jake Peavy and John Lackey, clearing out space for a retooled roster in 2015. The 2014 season is probably a lost cause, but the addition of Cespedes and the possible return of Lester in free agency would make Boston a team to watch in 2015.