Jon Lester made headlines this past weekend by hinting that a relatively bizarre scenario – one in which he would be traded to a contender before Thursday’s trade deadline but eventually re-sign with the Red Sox in the offseason – could ultimately take place.

“Yeah, why not?,” Lester told Comcast’s Sean McAdam. “I mean, [Boston] is what I know, this is what I love. Like I’ve said plenty of times, this is where I want to be. And if they trade me, I completely understand. No hard feelings.”

Lester is arguably the top starting pitcher in baseball currently on the trading block as he owns a 10-7 record, a 2.52 ERA and a 1.12 WHIP in 2014. Winning 10 games on a team that has just 48 of them total is no small feat. But potential playoff teams are no doubt salivating over Lester’s superb postseason history first and foremost. Lester has a sparkling 2.11 ERA in the playoffs, having played in eight different postseason series’ with the Sox. He would be the ultimate rent-a-player.

But once Lester is traded away, it will likely be quite difficult to lure him back to Boston in free agency. The lefty was lowballed by the Sox in spring training with an offer of four-years, $70 million and contract negotiations have sputtered and stalled since the perceived “slap in the face” by Boston management.


It’s hard to imagine Lester saying “all is well” this November when in one calendar year the Red Sox would have offered up a weak contract AND traded him. It’s far more likely Lester becomes comfortable with his new surroundings (wherever that may be), fresh off a potential October run, or goes to the top bidder on the free agent market. It’s unlikely that the Sox would get into any kind of mega dollar bidding war now, especially after they’ve proven that they’re capable of winning a World Series by using a patchwork approach that includes signing middle-of-the-road free agents.

A week ago, the possibility that Lester would be traded was small as the Sox clung to hopes that they could make a run, having won their first four games following the All-Star break. But the Blue Jays and Rays quickly changed Boston’s plans for a resurgence last week as the Sox went winless from Tuesday through Saturday. The Sox certainly seem to be in “sell” mode as the deadline nears as they are fresh off trading one member of their starting rotation already in Jake Peavy to San Francisco.

Follow Metro Boston sports editor Matt Burke on Twitter: @BurkeMetroBOS

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