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How will Red Sox ace Jon Lester define a hometown discount?

Posted by Adam Kaufman  February 24, 2014 01:14 AM

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Ever since Red Sox postseason ace Jon Lester told reporters at last month’s annual Boston Baseball Writers dinner that he’d like to remain in Boston for his entire career, to the point where he acknowledged a willingness to take a hometown discount to make that happen, I’ve wondered:

What defines a hometown discount?

When Lester said he’d have to have the Sox jersey ripped off his back and then reaffirmed those desires upon his arrival in spring training, what did he have in mind?

There’s a big difference, for instance, between what Dustin Pedroia did – which is accept a long-term deal for well below his market value – and requesting dollars that are simply in line with other top pitchers in the game, though a smidge below what he could maybe command in free agency.

Well, credit WBZ-TV’s Dan Roche for being the man in Fort Myers to prod the two-time World Series hero on Sunday’s “Sports Final”.

“Everybody’s hometown discount is a little bit different,” Lester told Roche, referencing that Pedroia accepted his extension when he was still a few years away from free agency. “I think you have to get in a room, sit down, and iron it out. I’m very optimistic on what we can do.”

Roche discussed his conversation with Lester prior to its airing on Friday’s edition of “Felger and Massarotti” on 98.5 The Sports Hub, and acknowledged a belief that Lester will be seeking around seven years and $150 million.

If the eight-year pro wants to be paid among the elite pitchers in the game, then he probably made a mistake in declaring he’d take a hometown discount.

Nine starting pitchers across Major League Baseball earn an average of at least $20 million a year for the length of their deals. They include Clayton Kershaw ($30.7M), Justin Verlander ($25.7M), Matt Cain ($25.5M), Felix Hernandez ($25M), Zack Greinke ($24.5M), Cliff Lee ($24M), Cole Hamels ($24M), C.C. Sabathia ($23.25M), and unproven (in North America) rookie Masahiro Tanaka ($22.14M).

Save for Kershaw, a 25-year-old stud with two Cy Young awards and a second-place finish on his resume, Lester could conceivably demand the same annual earnings as most any of the men listed above. He’s certainly no lower on the list than Hamels, who’s had a strikingly similar career to Lester.

If Lester wants that payday – which is well within his right, by the way – he likely won’t receive it in Boston.

Unless

While the term “hometown discount” lends one to automatically think in terms of dollars, it is possible Lester is also prepared to bargain over the years.

The Red Sox have shown over the last two winters that they’re okay with spending a bit more per season if it means that money is coming off the books sooner. Guys like Mike Napoli and Shane Victorino could speak to that first-hand. Moreover, there’s only one guy signed after the 2015 season and that’s Pedroia for $13 million. By comparison, the free-spending Yankees already have seven players under contract through 2016 for a whopping $155.1 million. That’s more than Boston’s entire payroll this year ($152.1M).

It’s unlikely – or at least it should be – that the Sox would hand Lester something in the neighborhood of seven years and $150 million.

But it’s not hard to envision the Red Sox’ offer arriving in the range of $22-25 million per year over five seasons in an effort to pay him top dollar while simultaneously avoiding the wretched back-end, late-30s years, when he’d almost certainly fail to live up to his salary.

Fortunately for general manager Ben Cherington and ownership, the Sox have some extra money to play with in the wake of Ryan Dempster’s decision to take a year off, which could benefit both Lester and the team.

If the club ripped up the pitcher’s $13 million contract for 2014 and started a new five-year pact, he’d be a free agent by age 35. In fact, starting now would even allow the Red Sox some wiggle room to extend Lester six years, which would end before he’s 36.

I’d qualify a “hometown discount” in Lester’s situation to resemble six years and roughly $135 million if it started this season, or five years and about $120 million if it began next winter. Given his talents and the absurd amount of money floating around the game with the additional television revenue, that seems fair for both sides.

However, it might behoove the Red Sox to wait through this season to see if they get the Lester who was among the best pitchers in baseball in the second-half of 2013 (7-2, 2.57 ERA, 1.19 WHIP) and into the postseason (4-1, 1.56 ERA, 0.95 WHIP), or the guy who struggled in the first-half (8-6, 4.58 ERA, 1.37 WHIP) and much of the 18 months prior.

David Ortiz 4.jpg

Lester, unlike his extension-seeking counterpart David Ortiz, has handled this situation perfectly. He’s never once publicly spoken about money, merely his hope to pitch in the only place he’s ever known as a professional. The newly 30-year-old lefty hasn’t received any of the backlash from “haters,” as Ortiz has termed those of us hoping he’ll just play out his current contract or at the very least limit his appeals to behind closed doors.

That’s because Lester has said all of the right things while never once threatening to test the market if things don’t pan out. He isn’t contributing to a potential distraction or suggesting he’s one of the greatest players to ever put on a Boston jersey (even if Ortiz is, it doesn’t need to be articulated by him), or pointing out that he’s playing for half his economic worth. That’s exactly what you want from a remarkably dependable and durable (he’s made at least 31 starts every year since 2008) two-time All-Star who’s put up similar stats through his 29th birthday to another star southpaw named Andy Pettitte.

But, in the end, it usually comes back to the money. If you took Lester’s praise of all that encompasses the Boston Red Sox to mean he’d do what Pedroia did and sign a Homer Bailey-like six-year, $105 million deal, then you’ve already reserved your spot on next fall’s parade route. He’s noted he doesn’t want to be the guy to lower the market value.

Boston’s a sports city like few others and Lester’s accomplishments are well documented and appreciated. As a result, he has nothing left to prove here. Should he play out his final year and test the market, he’ll be 31 and staring at the most lucrative offers he’ll see in his entire career. That’s tough to ignore, unless he really hates the idea of change and values winning first and foremost, as he’s said.

Everyone wants Lester to continuing calling Fenway home well beyond this season. The GM, the owners, his teammates, me and, I’d bet, you. Soon enough, we’ll find out just how strongly Lester feels and what he’s willing to leave behind to make it happen.

Follow me on Twitter at @AdamMKaufman

This blog is not written or edited by Boston.com or the Boston Globe.
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About this blog

Adam Kaufman is a writer and broadcaster who can also be heard regularly on 98.5 The Sports Hub, WBZ NewsRadio 1030, the national CBS Sports Radio Network, and broadcasting Boston College hockey games. The Massachusetts native is a Syracuse grad and a pop culture fanatic who offers a unique and entertaining look at your favorite Boston sports teams. Please don't hold his love for Jean-Claude Van Damme movies against him.

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