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Red Sox chance of getting Jon Lester at a 'hometown discount' has passed

Posted by Eric Wilbur, Boston.com Staff  January 24, 2014 08:58 AM

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So, Jon Lester said heíll take less money to stay with the Boston Red Sox?

Yawn.

Oh, thatís not to deny Lesterís sincerity over how he feels about Boston, or even the remote possibility that the lefthanded starter would indeed accept a deal that would be less than he could get on the open market next fall. Itís just that such comments have become so passť in the world of sports negotiations that itís difficult to take Lester seriously.

On slow days though, the admission apparently becomes a revelation.

Can we not treat this as if Lester were already signed, sealed, and delivered simply because he made some innocuous comments to the media at the surely-swanky Boston Baseball Writers Association of America annual dinner Thursday night? The lefty may be genuine in saying that he would be seeking "a Dustin Pedroia deal," the one the second baseman signed last summer that will pay him $110 million over eight seasons. Heíd also be stupid not to see the names Clayton Kershaw and Masahiro Tanaka and not realize what kind of value he may have on the open market as a free agent.

Only C.J. Wilson and Matt Moore won more games (17) last season among American League lefties, and Lesterís postseason career (6-4, 2.11 ERA) thus far puts him on track to be this generationís Curt Schilling. He may be 30, but thatís a year younger than Wilson was when he signed his backloaded five-year, $77.5 million deal with the Angels in 2011. Lesterís performance negated such conversations, but what might the Sox look like now had they signed their guy to a similar deal at the same time? Theyíd at least have another two years to play with while the likes of Henry Owens, Matt Barnes, Anthony Ranaudo, Brandon Workman, and Allen Webster completed their maturity to the big league level. Lester would be 32 at the end of the deal, and the Sox would probably have an easier time negotiating a contract not in the stratospheric level of Kershaw, and would have their groomed hurlers to fall back on should things not work out.

But if they let a lefthanded starter walk to free agency? See ya later.

Lesterís deal is going to dwarf the contracts handed out to Wilson and Mark Buehrle, who signed his four-year, $58 million contract with the Marlins at the age of 33. It wonít come near the $215 million Kershaw got or the $155 million the Yankees gave Tanaka, both of whom are only 25, but something in the range of five years, $100 million sounds likely. Remember when that was Manny Ramirez money?

Lester has won 100 games in eight seasons, but he's in the same category as James Shields (31 years old), as well as Cole Hamels and Adam Wainwright, both of whom have won 99 at the ages of 29 and 31, respectively. Shields is also a free agent after next season, and he and Lester will provide an interesting market for starters, should both make it to free agency. Hamels signed a six-year, $144 million contract with the Phillies back in 2012 at the age of 28. But Lesterís starting point is probably something like Wainwrightís five-year, $97.5 million extension that he signed with the Cardinals last March at the age of 31.

The St. Louis pitcher insisted last week that he was OK with signing a year away from free agency. "Do I think I could have made more money on the free agent market? Absolutely," he told the St. Louis Post-Dispatch. "But you canít buy happiness. Iím not going to be happier anywhere else than where I am right now."

Cardinals general manager John Mozeliak also recognized the timing, something the Red Sox missed out on in inking Lester a year ago as well. "Clearly if that (Kershaw's $215-million deal) was on the board today when we were trying to sign somebody like an Adam it would naturally pull it up. Weíre fortunate that the deal was done."

So, are Lesterís contract demands still on par with Wainwrightís a year later? If indeed they are, the Sox would behoove themselves to make such a deal by the time camp breaks in March. But the market would likely tell Lesterís on deck for more.

"I want to be here until they have to rip this jersey off my back," Lester said. "I want to stay here. This is what Iíve known. I grew up in this organization. Iíve had plenty of good and bad times here. I enjoy it, my family loves it here, all my son talks about is going home to Boston, and thatís what he thinks is home. If it all comes down to it, we want to be here."

You could reproduce that quote and bestow it upon dozens of Red Sox players over the years, from Clemens to Ellsbury. In the end, few take the elusive ďhometown discountĒ like Pedroia has done twice now.

Maybe Lester will too. But does the fact that the Red Sox havenít done anything about it as of yet send a signal as well?

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About the Author

Eric Wilbur is a Boston.com sports columnist who is still in awe of what Dana Kiecker pulled off that one time in Toronto. He lives in the Boston area with his wife and three children. Comments and suggestions for the best Buffalo wing spots are encouraged.

Contact Eric Wilbur by e-mail or follow him on Twitter.

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