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Turning down pitch for Lester was the right move

Posted by Christopher L. Gasper, Globe Staff  May 21, 2010 12:37 PM

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Sometimes, the best deals a general manager makes are the ones he doesn't.

That thought came to mind last night watching Red Sox ace (there should be no argument at this point) Jon Lester mow down the Minnesota Twins and author the first complete game of the season by a Red Sox starter.

If Sox GM Theo Epstein had capitulated to the sound and fury of talk radio, then Lester would have been the opposing pitcher last night for the Sox and not the superlative starter who needed just 84 pitches to get through the first eight innings against a Twins lineup that features MVPs Joe Mauer and Justin Morneau and ranks second in baseball in batting against lefties (.288 average).

Following the 2007 season, the Twins were peddling another pretty good port sider, a fellow by the name of Johan Santana. It was obvious that mid-market Minnesota wasn't going to be able to pay Santana the $100-plus million he wanted as he approached free agency. One of the shrewdest organizations in the game, the Twins had targeted Lester as a player they wanted in return for Santana.

Even though Lester had overcome anaplastic large cell lymphoma and started the clinching game of the 2007 World Series, it seemed like a no-brainer. Send Lester, a promising yet unproven prospect, to Minnesota for a two-time Cy Young Award winner and nonpareil lefty ace who had won the American League pitching triple crown (wins, ERA and strikeouts) a season before.

People salivated over the thought of a rotation with Santana and Beckett as its anchors. They implored Epstein to pull the trigger.

The Sox appeared open to swapping Lester, but after internal discussion and debate held steady. Santana was sent to the Mets.

It was not an easy or popular decision for the Sox brain trust to pass on Santana, whom many saw as the second coming of Pedro Martinez. You were eschewing a sure thing for a maybe. However, Epstein and others believed that Lester could one day be a pitcher of Santana's caliber at a much more palatable cost.

Two-and-a-half years later, it's pretty clear that the Sox made the right move by not moving Lester. The 26-year-old hasn't reached his prime yet, but he has become every bit the equal of the 31-year-old Santana at this point in Santana's career.

From 2008 until now, Lester has the best winning percentage of any lefthanded pitcher in baseball who has thrown at least 400 innings, posting a 35-16 mark (.686). The next best is Cliff Lee, who is 37-18, a .673 winning percentage. Santana is fifth at .640 (32-18).

But wins are an ancient and inconclusive way to measure a pitcher's effectiveness, agreed? Want to go new age? Let's take WAR (wins above replacement). Lester is tied with the Chicago White Sox John Danks as the lefthanded leader in that category over that time span (11.2). Second is Santana, 10.

Santana is one of the most dynamic punchout pitchers of his generation, baseball's version of a walking wind farm. Yet, among lefthanders who have thrown more than 400 innings during that span, Lester, who set a Red Sox record for Ks by a lefty last season with 225, has the best strikeouts per nine innings rate at 8.37. Santana's during that time is 7.80.

Santana is the lefty leader in quality start percentage with 75 percent of his starts qualifying as a quality start during the past two-plus seasons and his 2.90 is the second best among southpaws, trailing only Lee. Lester is fourth at 3.33. Batters have hit .238 off Santana during this span (third), and .245 against Lester (fifth).

But Lester is pitching in the American League East, where ERAs swell like the Banzai Pipeline. He also hasn't done himself any favors with his season-opening slumps. This year he was 0-2 with an 8.44 ERA in his first three starts.

As Mr. Touching All the Bases, Chad Finn, pointed out if you go to Lester's profile on the indispensable baseballreference.com the player he is most comparable to through age 25 is ... Johan Santana.

The two pitchers are comparable everywhere except compensation, and that is what makes holding on to Lester such a home run. After being traded to the Mets for a package of outfielder Carlos Gomez (since shipped to the Brewers for shortstop J.J. Hardy), and pitchers Philip Humber, Kevin Mulvey and Deolis Guerra, Santana signed a six-year, $137.5 million deal with the Mets.

He is making $21 million this season. Lester's entire five-year extension, which is in season two, is worth $30 million. He is pulling down $3.75 million this year. Furthermore, Lester is a safer investment. Santana had to shut it down last August and had offseason surgery to remove bone chips in his pitching elbow. Santana also pitched through a torn meniscus in his left knee in 2008.

In Patriots parlance, that is value folks.

Epstein is too diplomatic and too respectful of Santana to say it, but this might be the best trade he never made.

"The organization put a lot of faith in Jon Lester, and it's quite rewarding to see that faith repaid and then some," wrote Epstein in an e-mail. "To see him come out of our system and reach this level of success is a special thing for the organization, since so many people here care about Jon and provided support or advocacy through his development years and integration period into the big leagues."

Of course there is always a little luck involved as well. The Sox were seemingly ready to deal Lester to Texas following the 2003 season in a trade that also would have sent Manny Ramirez to the Rangers in exchange for Alex Rodriguez.

Sometimes, it's better to be lucky than good. When it comes to keeping Lester, the Sox were both.

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The word

Christopher L. Gasper riffs on the news


...That's what the Patriots have when it comes to picks in the 2013 NFL Draft, which starts Thursday. After all those years of stockpiling picks the way a survivalist does non-perishables the Patriots have just five picks in this year's draft, thanks to Band-aid trades for Albert Haynesworth, Chad Ochocinco and Aqib Talib. Five picks would be the fewest draft picks in franchise history. (Part of that is attributable to the trimming of the draft to just seven rounds in 1994). Further complicating matters is that two of the Patriots' greatest needs are at wide receiver and cornerback, positions where they have sustained draft droughts. With that in mind, I'm convinced the Patriots are going trade back out of the first round of a quanity-over-quality draft where you're just as likely to pick a Pro Bowl player in the second and third round as you are in the first round.

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