Why Are the Red Sox So Averse to Long-Term Deals? Blame This Guy

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Dec. 8, 2010. The day the nightmare began.

I’m not sure which is dumber: The fact that the Red Sox actually signed Carl Crawford to a seven-year, $142 million contract three-and-a-half years ago, or that they remain deathly afraid of negotiating long-term contracts with players because they were stupid enough to sign Crawford in the first place. If the Red Sox don’t want to commit to anyone over the age of 30, it should be a hell of a time watching the Pawtucket product at premium Fenway prices for the foreseeable future.

And so, this is where we are with Jon Lester, the man the Red Sox should be married to for the extent of his career, yet a player with whom they find themselves frightened of commitment. The floozies? Crawford and Adrian Gonzalez, two players who had never stepped foot in Fenway Park as Red Sox players, never did a damned thing to help the franchise win anything, received almost $300 million in salutations in one offseason.


Lester, the guy who has only won two World Series in Boston, has been a role model for the Dana Farber Institute, and is on track to become one of the winningest pitchers in Boston baseball history is about to get the “It’s not you, it’s me” speech from Larry Lucchino. It sucks.

The lefty has more than likely made his last start in a Red Sox uniform. Lester was scratched from Wednesday’s outing against the Blue Jays at Fenway Park, with reports and rumors swirling that a trade was imminent, with the Cardinals, Pirates, Dodgers, Marlins, and A’s reportedly all in the mix for his services. If that’s it, let the record show that Lester’s last appearance at Fenway Park was an eight-inning, four-hit shutout in which he struck out eight against the Kansas City Royals. Not shabby.

Sure, there’s risk signing Lester to a long-term deal, and history can show that teams willing to do so can pay drastically toward the end of the deal, much like the injury-riddled,34-year-old CC Sabathia in New York. But Lester is only 30. It’s not like we’re talking Charlie Hough here. Besides, has there been a more durable starter in recent Red Sox history than Lester? He’s made more than 30 starts every season since 2008, and has pitched more than 200 innings five out of the last six seasons. He’s ninth all-time in wins in franchise history with a 110-63 record and has been a key component in a pair of Red Sox World Series victories. By design and résumé, he seems the kind of guy you buy the diamond for, even more so than teammate Dustin Pedroia, whose recent performance just might also give the Red Sox pause when talking long-term.


Since signing a new, team-friendly, seven-year, $100 million extension last summer, the Red Sox second baseman has been a puddle of the Dusty Two Sacks fans had been accustomed to watching grind on a nightly basis. He’s on pace to have career lows in batting average, OBP, slugging (currently .365; Pedroia has never has a percentage lower than .400), and home runs. Yet it was only just over a year ago when the Red Sox stuck with him long term, just about a month shy of his…ready?…30th birthday.

Granted, position players are a different story from once-every-five-days starting pitchers when it comes to talking numbers, and as good as Lester is, he isn’t Clayton Kershaw, even though he’s about to be paid like the Dodgers hurler in the offseason. But nor is he Crawford, the malignant square peg who saw the Red Sox needing to make a point – whether it was to local fans or John Henry’s new, watchful eyes in Liverpool – that they weren’t afraid of spending money, a factor most already understood, confused only by the notion that the team was now spending it like Montgomery Brewster. It was only natural for Crawford to take the money, whine later.

“I thought I was stuck in Boston for seven years,” Crawford so fondly recalled on Tuesday when discussing the potential of long-term contracts being on the move before Thursday’s trading deadline. “I was out of there in a year and a half.”

Carl Crawford isn’t the worst signing in Red Sox history, he is the worst signing in Major League Baseball history, an exorbitant sum awarded to a player who, since getting paid, has yet to break the .800 OPS plane that used to be his norm. The Red Sox, a team that preaches patience at the plate and stresses the importance of on-base percentage, signed Crawford after a season in which his OBP of .356 was only 44th-best Major League Baseball, and that was the second-best mark of his career. Over 76 career games at Fenway Park, Crawford’s numbers were pedestrian, to be kind: .275 average, .301 OBP, .708 OPS.


Basically, he made no sense for Boston, which already had Jacoby Ellsbury playing center field. But, as Terry Francona laid out in his book, Tom Werner wanted to start winning in “more exciting” fashion, a notation that I, 100 percent, no doubt about it, believe was the impetus for the Red Sox landing Crawford. He was flash. He was TV. He was a disaster of epic proportions. Kind of like “Sox Appeal.”

These days, the team would rather go short-term with the likes of Stephen Drew and A.J. Pierzynski, which says nothing of the ability of the player, just the deal that the team tends to like. Oh, they’ll give you $10-$20 million, just so long as you stick around for no more than a couple years. Remember the days when they were dropping $51 million just to talk to Daisuke Matsuzaka?

We all know how that one turned out as well. But not everybody else is Jon Lester, and the fact that the Red Sox seem intent on treating him no differently is going to have reaching ramifications on this club for some time.

The Red Sox may not be still paying Carl Crawford, but there’s no doubt that Red Sox fans are still paying for him. This time, the price is Jon Lester.

What a farce.

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