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In Jon Lester debacle, Red Sox blew it in epic fashion

The Red Sox traded Jon Lester to Oakland in July.
The Red Sox traded Jon Lester to Oakland in July.Getty Images/File

The Red Sox are hard at work assembling a pitching staff for 2015. They want to put the botched Jon Lester negotiation in the rearview mirror.

Not quite. Not yet.

Regarding the Lester debacle, it's all about spin and you have to decide if you buy the spin.

You can nod your head and note that the Cubs are idiots for signing Lester to a six-year contract that will end up paying him between $155 million and $170 million. You can agree the Sox were smart not to commit those monies to a starting pitcher over 30. You could also buy into the notion that Lester said he'd take a hometown discount, then turned around and went for straight, hard cash. You can swallow the party line that the Sox really tried to do right by their ace and by their fans.


Or you can come to your senses and realize that the Sox bungled this "negotiation'' in epic fashion and now will have to work harder, surrender more, and probably acquire less (Wade Miley, Rick Porcello, and Justin Masterson, thus far) than what they had in front of them the whole time.

Jon Lester is not Babe Ruth. He's probably not going to the Hall of Fame like Carlton Fisk. But his unnecessary departure from the Red Sox in the prime of his career takes its rightful place on the medal platform of Red Sox mistakes. Let's give the Sox owners a tarnished bronze for strategic buffoonery in the wacky world of free agent negotiating.

This was a player who wanted to stay here. This was a player who was professionally born and raised in the Red Sox organization and played an integral role in two championship seasons. This was a stoic southpaw who beat cancer, never missed a start, kept his mouth shut, set an example for younger players, and pitched his best in postseason games. He bought a house in Newton. He talked about how much he hated change. He knew his way around Fort Myers and Fenway and he didn't want to learn any new roadways or meet any new trainers.


He was satisfied with restaurant options at the Bell Tower in Fort Myers, and he was happy with Pookie and Tommy in the Red Sox clubhouse. He even figured out a way to deal with the carnivorous Boston media. He'd mastered the proverbial Boston baseball experience and he told us last January he'd take less money to keep pitching here.

And then the ham-handed, glacial-moving, "we are the champions" Red Sox tried to exploit his public loyalty by issuing a hideous and late starting offer in March. We can all agree that $70 million is a huge bag of money — and that starting offers are never final offers — but the opening bid by the Sox was an insult to Lester's intelligence (less than half of the package the Tigers were offering Max Scherzer at the same time) and a clear signal that the Sox owners wanted Lester to forgo his market value for the privilege of pitching for the Red Sox. They reminded Jon that he could "finish his legacy" with the Red Sox. Meanwhile, principal owner John Henry, who also owns the Globe, was on record stating he agreed with a report that claimed signing players over 30 to long-term contracts was bad business.


Mindful of what was happening, and where this was going, Lester and his people stopped negotiating. The Sox still express surprise and dismay about this.

In July, they traded him. They dumped him while they could still get some value. And we got the iconic photo of Lester and Henry embracing (a.k.a. "The Fredo Hug") in the Sox players parking lot.

There was only one way the Sox were going to get Lester after that. Stripped (by their own hands) of negotiating exclusivity, the Sox were going to have to compete for Lester in the open market. And anyone who's paying attention knows the Red Sox never had any intention of going where this was going to go. In my opinion, they are secretly relieved he turned down their final offer of $135 million over six years. Their final offer enables them to satisfy the PR machine, but the Sox never really wanted to do this for a starting pitcher over 30. They just wanted you to know they were grudgingly willing to do it.

So we all went through the motions and fans got their hopes up. Lester cordially met with the Sox in November. He listened to Boston's opening winter offer of $110 million to $120 million. He probably appreciated the idea that the Sox were changing their rules for him. He listened to John Henry again last Friday. He knew the Sox had a ceiling of $135 million.


Hefty, but not competitive (it's $35 million less than what Lester stands to earn). The Sox get to say they tried, but that ultimately Lester changed his mind on the hometown discount and went for the money. Some of you will buy that.

No. The hometown discount went away when the Sox opened negotiations at exactly $100 million less than Lester's eventual value. Then they traded him, which made him more attractive to bidders, because it eliminated the first-round draft pick compensation. The list of players who re-signed with teams that traded them months earlier is very short.

In the final analysis, one has to wonder how much the mutual hatred between Larry Lucchino and Theo Epstein played a role in Lester landing at Wrigley. These are two brilliant, stubborn men. Theo was not going to lose a bidding war that involved Larry. And John Henry and Larry were not going to let Theo hijack their payroll the way he did in the winter of 2010-11, when Carl Crawford and Adrian Gonzalez were brought to Boston.

Speaking of Henry and Lucchino, where was ownership when all this came down Wednesday? When the Sox committed $200 million to Pablo Sandoval and Hanley Ramirez — two players who've accomplished nothing in Boston — Henry met with reporters for a victory lap and a clarification of policy (the principal owner asserted that his stance on signing players over 30 to long-term deals had been overblown).

There's been no comment from Sox ownership in the wake of the Lester departure. Ben Cherington and John Farrell were left to explain the failure of the negotiation.


Too bad. This was not Cherington's call. This was ownership's call.

The Cubs no doubt overpaid for Lester. They'll probably never win a World Series, and the final years of the Lester pact might look ridiculous. Meanwhile, there is no reason the Red Sox can't build a respectable pitching staff without Jon Lester. Miley, Porcello, and Masterson represent a beginning.

But this did not have to happen. The Sox should have locked up Lester last spring. They simply blew it — the way they blew it with the Babe and Pudge all those years ago.

Related coverage:

Red Sox trade for Rick Porcello, add Justin Masterson

Red Sox close to deal for Diamondbacks' Wade Miley

Red Sox need new pitching pieces — and have ways to get them

With Jon Lester off market, what's next for Red Sox?

Follow Dan Shaughnessy on Twitter at @dan_shaughnessy.