Tony Massarotti

Lackey Leveraging His Way Out

This is just a guess, but here goes: if the Red Sox had been 34-28 instead of 28-34 entering last night’s game against Baltimore, John Lackey wouldn’t be threatening retirement. But with the Red Sox now looming as sellers in a month or so, well, anything goes.

And so what Lackey is doing right now is executing his exit strategy.

In case you missed it, the respected Ken Rosenthal of FOX Sports reported yesterday that Lackey might retire rather than play for $500,000 he would currently earn next season. LackeyWins.pngThat salary figure was negotiated into his contract as a club option if and when Lackey had Tommy John surgery during the life of his current contract, a development that took place following the cataclysmic 2011 season. That injury effectively turned Lackey’s contract from a five-year, $82.5-million deal into a six-year, $83-million contract.

So what is Lackey doing now?

Making sure that he gets a say in where he ends up if and when the Red Sox trade him.

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Think about it: as we wrote here at the end of last month, Lackey has great value as a trade chip. He has two World Series titles and has pitched well in the postseason. He is at or near the top of his game. And thanks to that contract, he is effectively signed through next season – and for short money – making him the ideal acquisition for a team (in a large market or small) with any designs on a championship in 2014 or 2015.

And then, when Lackey departs via free agency – again, thanks to that contract – the new club would likely be entitled to draft-pick compensation.

Lackey knows all of this … which is why he is already starting to leverage his place in the process. The timing of the Rosenthal report is not a coincidence. The trading deadline is now seven weeks away as the Red Sox continue their flat spin into oblivion, and Lackey, like many, knows things may not turn around. As a result, he is not about to stand by and let the Red Sox decide his fate, particularly when he might be able to leverage his way back to a place like, say, Anaheim.

Red Sox: We think we have a trade worked out for you, John.

Lackey: Did I mention I might retire after this season?

Red Sox: It’s to Anaheim.

Lackey: Scratch that. Did I mention I’d consider an extension instead?

Of course, Lackey’s stance here was downright predictable and is tactically smart. It’s also a little weasel-like. When the Red Sox signed Lackey, both sides knew Lackey would likely face Tommy John surgery at some point. That’s why both sides agreed to a potential sixth year at the minimum major league salary. (The Red Sox wanted five years of service.) That deal had all the fingerprints of Sox president Larry Lucchino, and some Sox officials at the time whispered that then-general manager Theo Epstein never wanted to do the deal.

Remember: the Sox had money to spend that offseason. Things had broken down with Jason Bay. They needed an outfielder but stopped short on Matt Holliday. So they gave the money to Lackey, a then-31-year-old pitcher with elbow issues, the kind of free agent that flew in the face of Epstein’s general approach in free agency.

In Lackey’s defense, what he would argue is that he pitched the entire 2012 season (or at least most of it) with a torn elbow ligament when he should have had surgery much, much sooner. He pitched through it because the Red Sox, on their way to a historic collapse, were breaking down everywhere else. So Lackey took a bullet and posted a 6.41 ERA that is easily the worst of his career, then sat out all of 2012 before coming back to help the Red Sox win a championship.

As far as John Lackey is concerned, it seems, he and the Red Sox are even.

So we ask you:

Are they?