Pain of loss of Lester cuts deep

But the Sox, burned by the seven-year contracts they bestowed on the ill-fitting Adrian Gonzalez and Carl Crawford, have taken a pledge not to be fooled again. Despite the payroll flexibility to do so, and a fan base that pays a premium in expectation that they will be rewarded with the best, the Sox drew a line in the sand with Lester.

John W. Henry is fundamentally right that six-year contracts for players north of 30 are never a good idea. The game is littered with examples of how utterly foolhardy they can be. Maybe it will take a big-market owner or two to force the industry to reassess how they do business. Except in a business as awash in cash as baseball is these days, no one seems to mind much.

But Lester possesses all the traits of the exception to that rule -- strong and durable and dependable, and a pitcher already transitioning from the power thrower of his youth to the master craftsman he is today.

How do the Sox replace Lester? To Cherington's credit, he has assembled as talented and deep a group of pitching prospects as the Red Sox have ever had. But they are simply that -- prospects. If one or two of the group flourish in the big leagues, the Sox will be ahead of the game. You don't win pennants with prospects on the hill. Dave Dombrowski is collecting Cy Young Award winners (three of them) in Detroit. Billy Beane in Oakland has added two aces in the span of 3 1/2 weeks. Ned Colletti paid $300 million for the spiritual descendant of Sandy Koufax in Los Angeles, Clayton Kershaw.

The Sox and Cherington, meanwhile, are countering with maybes. Joe Kelly? Some promise, to be sure, but if he was still with St. Louis when Lackey joined the team, he's the guy who likely would have lost his spot in the rotation.

Cherington admitted Thursday the club will be in the market for starting pitching, either via trade or free agency, in the offseason.

Talk to certain people, and they will tell you that the Red Sox are truly planning to make a full-court attempt to re-sign Lester as a free agent, maybe even give him the five- or six-year deal he is seeking, paying him an average of $23 million a year.

Pull that off, and Sox owners are now the smartest guys in the room. They flipped Lester to acquire Cespedes, and then got Lester back, too. Pure genius.

Except there is no reason whatsoever to believe it is anything but wishful thinking. Name one thing the Sox have done to this point with Lester that would make you believe they will execute that plan. The low-ball $70 million offer in the spring? The inability to communicate a willingness to make a market-based offer? The embrace Henry gave Lester as the pitcher left the ballpark on Thursday?

Never mind that by allowing him to reach free agency, Lester is liable to receive offers that will dwarf the parameters of the deal the Sox supposedly will offer, especially because, as a player traded in midseason, any team that signs him will not have to surrender a draft pick as compensation.

So, the Red Sox will offer bread and circus and Cespedes, at least for the one year he has before he, too, can declare free agency. And Jon Lester will take his winner's pedigree to Oakland, and John Lackey his to St. Louis, and win some more.

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