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Dave D'Onofrio's Sox Beat: The case against trading Lester

July 26. 2014 8:23PM
St. Petersburg, FL, USA; Boston Red Sox starting pitcher Jon Lester (31) throws a pitch during the first inning against the Tampa Bay Rays at Tropicana Field. (Kim Klement-USA TODAY Sports)

AS the Red Sox slog toward Thursday's trading deadline in sell mode for the first time in 17 years - even during the disastrous Bobby Valentine season of 2012, they entered August a couple games over .500 - one principle should govern future decisions made by Plainfield-bred general manager Ben Cherington.

Those for whom there is a plan next season can stay. Anyone else can go, if not for the value they'll fetch in return then for the opportunity to clear a roster spot and begin evaluating a farmhand with the future in mind. Jake Peavy is already gone, traded to the Giants Saturday in exchange for two Triple-A pitchers, Edwin Escobar and Heath Hembree. Jonny Gomes and Stephen Drew may be next in line to head elsewhere. Felix Doubront, the team having soured on him to the point it seems a change of scenery may be mutually amenable, is another candidate for departure.

If a player is free to leave at season's end anyway - as was the case with Peavy and is the case with Gomes and Drew - or if he doesn't cleanly fit within the club's vision for 2015 - as appears to be the case with Doubront - there's no sense hanging on.

Except in the case of Jon Lester.

The left-hander can't be considered part of Boston's plans for next season. His impending free agency means he might not even be here, and principal owner John Henry saying that the two sides won't talk again until after the season suggests the team and the player are still not close to an agreement on the terms of an extension. If that's true, Lester probably will reach the open market, and he could then escape to whichever team opens its wallet.

If he does, all the Sox will get in return for their ace is a compensatory draft pick. So, as the team all but sealed its fate of failure by losing three of four in Toronto last week, the idea of trading Lester publicly gathered some steam. It's an idea motivated by thinking that the Sox could get more than merely draft commodity by dealing their postseason horse to a pennant contender, and it's justified by interpreting the club's resistance to making a deal now as an indication that the team doesn't really want to retain Lester - for fear of paying a pitcher big money into his mid-30s.

Both factors constitute a logical mindset. But that doesn't make trading Lester a good idea.

First, in terms of his trade value, Lester would be a rental for whichever team acquired him, which most likely would diminish what the Sox would get back in return. The goal would be a good prospect, but teams may be reluctant to exchange the elite assets of their systems for 10 starts from Lester.

There's a reason Jeff Samardzija and Huston Street fetched upper-tier talent for their former teams, why David Price's name is being bandied about now, and, heck, why the Red Sox were willing to part with the rising Jose Iglesias for an aging Peavy a year ago. The acquiring team tends to pay a premium in midseason deals when it controls the player for at least another season.

Boston doesn't have that leverage - but, that said, it would only take one team desperately seeking to put itself over the top to make Cherington an offer he'd struggle to refuse. So it's really the second factor where the idea of trading Lester falls apart: the assumption that the Sox, by low-balling him to this point, don't want to sign him.

Maybe they were - and are - simply paying attention to the market.

After all, since the start of the 2012 season, eight pitchers around the game have signed contracts worth at least $100 million. One was Masahiro Tanaka, whose only choices were to sign with the Yankees or stay in Japan. One was Zack Greinke, who inked a six-year, $159 million deal with the Dodgers. The other six were all contract extensions, signed with the pitchers' current teams before the players got to the open market.

On the other hand, over that same time period, seven pitchers went to free agency and received contracts of at least four years. Greinke hit it big, but after that, Anibal Sanchez - at five years and $88 million - was the only other one to put his signature on a pact worth more than $52 million.

So while it makes sense to think Lester will get paid more as a free agent than he would by agreeing to stay in Boston, recently that hasn't proven to be true in other cases around the game. The Red Sox are obviously aware of that. Just as they're aware that Adam Wainwright signed a five-year extension with the Cardinals worth $97.5 million in March 2013, when he was 31 - the same age Lester will be when he throws his first pitch under his next contract. Age is a major factor for the Sox, but it appears to also be for almost every other team, too.

Look at it in light of those facts, and suddenly the Sox' reported offer of four years and $70 million seems far less an insult than a starting point. It's still probably nowhere near where the number winds up, especially given the year the lefty is having for himself. But based on what's going on around baseball, it shouldn't close the door on negotiations.

And that's another reason not to trade Lester. Boston isn't going to the playoffs, so from the end of the regular season to the end of the World Series, the Red Sox would have exclusive negotiating rights. All along Lester has indicated a desire to table talks to avoid distractions; now the Sox would have four weeks to make their sell.

Meanwhile, Lester's agent would have a chance to feel around and gauge interest in his client (below board, of course). Maybe both sides get a better grip on the reality of the market at that point - and with that understanding comes a deal. Maybe they come to a place that puts the Sox in a competitive position when the pitcher starts fielding offers. Or maybe they agree that it's not going to work.

But if Lester is someone the Sox have any desire to keep in their plans moving forward, they should stick it out. Stick by their plans. And stick with Lester.

STAT of the week: When the Red Sox opened the stretch in which they won eight of nine around the All-Star break, they were 10½ games back in the division, in fifth place, and 10 games back in the wild-card race, 13th in the AL. They entered Saturday 10½ games back in the division, in fifth place, and 7½ games back in the wild-card race, 12th in the AL - with 13 fewer games to make up the gaps.

Dave D'Onofrio covers the Red Sox for the New Hampshire Union Leader and Sunday News. Email him at

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