Boston and Jon Lester: The breakup

Jon Lester said goodbye to Boston Sunday with a full-page ad in the Globe, with endearing pictures of the pitcher, family and the World Series trophy he twice helped the Red Sox win.

It was a cute and classy gesture, whether it was Lester’s idea or a media-savvy agent’s. It was no doubt appreciated by the Globe, which is owned by John Henry, who also owns the team Lester used to pitch for. (Perhaps full-page ads by traded stars can help salvage the newspaper industry; David Price had one in the Tampa Bay Times Tuesday. Single, there were no family pictures, and alas, no World Seres trophy).

And it was savored by Red Sox fans, in whom the ad stirred a yearning. Maybe it was a hint, they thought, like the paramour who rekindles an affair on the pretense of leaving a toothbrush in the bathroom. Maybe it’s not over.

Those fans are as delusional as the Red Sox were when they thought Mike Aviles could be their everyday shortstop in 2012. Remember how that turned out? Remember how in 2011 (editor’s note: a previous version said 2012) Lester and John Lackey (with Josh Beckett) were two-thirds of the chicken and beer and video games gang? If Lester had been traded then, his thank you wouldn’t have been a full-page ad but six lines of a classified ad.

Here’s the reality, Red Sox fans. It’s over. Cherish your memories, but Jon Lester won’t be walking through the Red Sox’s locker room doors any time soon, no matter what he said in his farewell. If the Red Sox couldn’t sign Lester when he offered to accept a “hometown discount” this spring, they’re not going to sign him this offseason for more money, more years and more commitment.

Just as LeBron James wasn’t going back to Miami when he opted out of his contract, Lester isn’t coming back to Boston once he’s been traded. He’s more likely to be in pinstripes next season, which may sting, but may not necessarily be a bad thing by 2018 — think about the 4.78 ERA the Yankees got back for the $23 million they paid CC Sabathia last year, the eight starts with a 5.28 ERA they got for the $23 million they’re paying him this year, or the $48 million they still owe him for the next two.

Well-compensated free agents and their suitors don’t always live happily ever after.

Lester will be the former, and how. In his first nine seasons he’s been paid $43 million for a 30.9 measure of WAR. It’s fair to say he’ll be paid that much over his next two seasons; it seems fair to guess it’ll take six or seven seasons — the full length or most of his next contract — to accumulate that much WAR.

The Red Sox, who built a World Series champion in 2013 on shorter signings, home-grown talent and good card sense, won’t pay it. Not because Lester hasn’t been worth it — five of his last seven seasons have been $20 million-plus worthy, and last year’s postseason sure was — but because five of his next seven seasons might not be. And/or because season-ending injuries are an occupational hazard. (Sabathia was six months younger and had accumulated 2.2 more WAR when he signed with the Yankees for eight years and $182 million; his previous two seasons he had averaged 247 innings per).

Washington warned in his Farewell Address “against the insidious wiles of foreign influence …” If he were a general manager today, he’d be more concerned about the insidious effects of long-term contracts. The Red Sox have only one, and it should already be giving them pause. Dustin Pedroia, who is still owed seven years and $96 million, is having a career-worst season in 2014 by 61 points of OPS.

No one minded that his previous worst season was the last one, because it was only by 10 points and despite it, the Sox went from worst to first. It might not be so easy to be flippant about Pedroia’s slippage if the Sox go from first to worst and stay there.

The Sox wanted flexibility on future rosters and not entanglements, and they wanted to enter 2015 with short-term talent and not long-term commitments. If there’s a Contracts Anonymous, they’re in it, having sworn them off after spending $354 million on Adrian Gonzalez, Carl Crawford and Josh Beckett, and needing the Dodgers to save them from themselves.

Last year’s 2013 World Series title exempted the Red Sox from criticism when Jacoby Ellsbury became a Yankee (and rightfully so, given the $22 million they’re paying for his 2.7 WAR at age 30, with six more years to go). And they were widely praised for acquiring Yoenis Cespedes, an intriguing package of power and defense, for Lester (who does have a career .318 on-base percentage).

But Lester isn’t returning — if he did, it would be the most unlikely signing since the Phillies traded Cliff Lee because they couldn’t afford his $9 million and recently acquired Roy Halladay’s $15 million for 2010, then signed Lee back a year later for $21 million per.

And look how that turned out.

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