We’ve Seen the Red Sox-Jon Lester Negotiations Before – When Boston Lost Roger Clemens

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Roger Clemens pitched his last game in a Red Sox uniform on Sept. 28, 1996. Will Jon Lester do the same on Wednesday? Barry Chin/Globe Staff

Jon Lester isn’t Roger Clemens.

In nine years with the Red Sox, Lester has 82 fewer wins than Clemens and Cy Young (each with 192, Clemens over 13 seasons, Young over eight) in a Red Sox uniform. He’s fourth all-time in strikeouts with 1,386, trailing Pedro Martinez by some 300, and a long way from catching Tim Wakefield and Clemens, both with over 2,000 (Clemens, obviously, is No. 1 with 2,590 during his time in Boston). His 1,519 1/3 innings pitched are 11th-most in team history, just behind Lefty Grove. Wakefield (3,006) and Clemens (2,776) lead the way. Lester’s career 1.29 WHIP (18th-best all-time in Boston) pales in comparison to Clemens’ 1.16 (ninth).


Then again, Clemens never won a World Series while with the Red Sox. Lester has won two.

But where the differences in Boston end comes a striking similarity in the ways in which they may both leave via free agency. At 33, Clemens was three years older than Lester when he was playing out his final days in Boston, where – surprise – the Red Sox hoped to lowball their ace and get him to sign a deal for “more than one year.” It’s amazing to figure that didn’t work out, huh?

“We want Roger to finish his career with us,” owner John Harrington told the late Will McDonough in July of the ’96 season. “This is the way we would like to have it end. We’ve told Roger that, and he told us that he wanted the same thing. When the year is over, we’ll try to get a new contract done. With his age, we will not be thinking long-term, but we’ll offer him a deal for more than one year and a deal that will recognize his contributions to the ball club over the years.”

The Red Sox had no intentions of seeing what they could get for Clemens at the trading deadline (they did however, surrender Jeff Manto to the Mariners for Arquimedez Pozo!), unlike the baseball ops folks have explored this time around with Lester. As the Globe’s Nick Cafardo wrote as the deadline approached in ’96:


“While Clemens bashers are ready to ride him out of town and down yonder to Houston, Clemens has veto rights on trades and he’s made it very clear he wants to stay in Boston. His contract is up after this season and the Red Sox might mess these negotiations up royally because they’ll enter them looking for a bargain. Will they get it?

According to Clemens’ agent, Alan Hendricks, the Red Sox would receive a discount, but this won’t be Filene’s Basement. With most astute baseball people understanding that Clemens’ 3-8 record is misleading because the Sox have scored two or fewer runs in nine of his 19 starts, it would be interesting to see what he would command on the open market. Some team likely will offer $15 million over three years.

All indications are that the Sox want Clemens around to anchor what soon will be a young pitching staff. Clemens’ presence is good for Sele, as it will be for Jeff Suppan when he’s recalled from Pawtucket sometime this month, and for Robinson Checo when he’s finally sprung from the Hiroshima Carp. Those who witnessed a young Clemens with Tom Seaver in 1986 understand the value of having a young pitcher pick the brain of a legend. Clemens would spend hours talking pitching to Seaver, and there’s no doubt he adopted many of Seaver’s mannerisms.”

There’s so much golden hilarity in there, I’m not sure where to begin.

First off, there was no “hometown discount,” as Clemens signed a four-year, $40 million deal with the Toronto Blue Jays, not exactly the $15 million over three years that some rogue team might offer up. Second, the thought of Clemens anchoring a promising staff of Sele, Suppan, and Checo should serve as a grand warning to anyone expecting Rubby De La Rosa, Allen Webster, Henry Owens, Brandon Workman, and Anthony Ranaudo to be the second-coming of the Glavine-Smoltz-Maddux Atlanta Braves.
According to McDonough, “Harrington says the Sox’ promising group of youngsters is one reason Clemens would like to stay here. ‘He knows we have some kids coming along in the next couple of years that are going to make us a much better team.’”


So, now as it pertains to Lester (who is a target of trade discussions leading up to Thursday’s deadline, making some wonder if Wednesday night may be his final start in a Boston uniform), if the 30-year-old lefty were keen on taking a “hometown discount” he might have counter-offered the Red Sox’ $70 million offer in spring training. But Lester has been here some time now, which is to say, he’s seen the irresponsible way the Red Sox spent money on Carl Crawford. He’s aware of how they committed to Adrian Gonzalez to the tune of $154 million, even before they understood that he possessed all the charisma and accountability of a mailbox.

All Lester has done is help win the city a pair of titles over nine durable seasons. And he’s the one that has to be dinked around? Conveniently though, the Sox all of a sudden don’t like giving out long-term deals to players over 30. Crawford and Gonzalez were both 29 and signed SEVEN-YEAR deals. Where’s the hypocrisy rooted?

On Dec. 15, 1996, the Globe ran an editorial on Clemens’ departure that included the following passage:

“If Clemens returns to form, as Young did in his first Red Sox season, Boston fans will be plunged into gloom and recrimination. But lengthy contracts require a long-range perspective by fans as well as players and owners. The real significance of Clemens’ move will not be known until the end of the 1999 season. Clemens and the Red Sox made sensible decisions in an uncertain universe.”

Clemens went on to win 162 more times over the next 11 years.

Lester? Well, that’s seemingly the risk the Red Sox are ultimately willing to take.

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