Rosenthal: What'€™s holding up new deal between Red Sox & Lester?

If the Red Sox want to keep left-hander Jon Lester, signing him to a long-term extension shouldn’t be all that difficult.

Jon Lester has a career 3.76 ERA in his eight-season career, all of which has been spent with the Red Sox.

Andrew Weber / USA TODAY Sports

If the Red Sox want to keep left-hander Jon Lester, signing him to a long-term extension shouldn'€™t be all that difficult.

The market for free-agent starting pitchers is well-established. In fact, a pitcher comparable to Lester, Tigers righty Max Scherzer, recently turned down a six-year, $144 million offer, according to FOX Sports 1's Jon Paul Morosi.

Lester and Scherzer are about the same age and eligible for free agency at the end of the season. Their career ERA-pluses — that is, their ERAs adjusted to league and ballpark — are almost identical. Lester's postseason numbers are superior, and indeed fairly historic.

Six years, $144 million also was the size of the extension the Phillies awarded lefty Cole Hamels on July 25, 2012. Hamels and Lester, too, are similar, but Hamels began his new deal at 29 and Lester will begin his at 31.

Contract numbers get larger with inflation — Homer Bailey received a higher average salary on his extension than the superior Jered Weaver did 2½ years ago —€” but Lester is on record as saying he will give the Red Sox a hometown discount.

So it's probably safe to peg Lester's goal in the five-year, $110 million to $120 million range, if not six years in the $135 million to $145 million area.

The Red Sox probably want to hold Lester closer to five years, $100 million, though that seems light, considering they gave righty John Lackey a five-year, $82.5 million deal in free agency four years ago.

Lester is left-handed, increasing his value. He also wants to continue pitching in a hitter-friendly park and division, and has proved he can withstand the scrutiny of baseball-crazed Boston.

So, what exactly is the problem?

I'€™m not sure there is a problem, though from the outside, the negotiations do not appear to be moving briskly. Red Sox general manager Ben Cherington told reporters Monday that the two sides continue to talk and that the team wants resolution by Opening Day.

For all anyone knows, a new deal could get announced any moment. Yet, if you're mindful of the Red Sox's pattern of parting with free agents, you actually would bet against an extension of this magnitude. That eight-year, $110 million deal that second baseman Dustin Pedroia signed last July 24? It is so absurdly club-friendly, it almost shouldn't count.

Pedroia could have received tens of millions more if he had just waited five months for Robinson Cano to raise the bar for second basemen in free agency. Cano certainly did his part, agreeing to a 10-year, $240 million contract with the Mariners —€” more than double what the Red Sox gave Pedroia.

There are two differences, though, between Pedroia and Lester, even though they are represented by the same agency, ACES:

* Pedroia was 2½ seasons away from free agency when he signed his deal, while Lester is a little more than seven months away now.

* Pedroia did not object to signing a deal that was ridiculously below-market, while Lester almost certainly has a different definition of the hometown discount that he is willing to give the Sox.

So, how far will the Red Sox push?

Recent history suggests pretty far.

 

 

Since 2004, when the Sox won the first of three World Series championships in 10 years, the team has retained only six of its 89 free agents on multi-year deals.

The biggest of those contracts was catcher Jason Varitek’s four-year, $40 million agreement after the ’04 title. Extensions such as designated hitter David Ortiz’s new one-year, $16 million contract (with club/vesting options for 2016 and ‘17) do not figure in the total. A Lester extension wouldn't count either, but if he gets to free agency, look out.

Meanwhile, the free agents the Sox have lost since '04 form quite an illustrious collection.

We're talking about right-handers Derek Lowe and Pedro Martinez, outfielder Johnny Damon, third baseman Adrian Beltre, catcher Victor Martinez, closer Jonathan Papelbon, outfielder Jacoby Ellsbury and likely Stephen Drew, among others.

Removing emotion from the process mostly serves the Sox well — many of their decisions proved quite shrewd, from Martinez to Jason Bay to Papelbon. But Lester, the team'€™s second-round pick in 2002, is homegrown. He survived a form of lymphoma that was diagnosed in 2006. And he went on to go 6-4 with a 2.11 ERA in 13 postseason appearances, including 3-0 with a 0.43 ERA in three World Series starts.

Sure sounds like an exception, no?

Don't get me wrong: It'€™s the Red Sox'€™s prerogative if they don'€™t want to go long-term with any pitcher —€” Lester is coming off a career-high 248 innings last season, including playoffs, and he almost certainly will not be as good from 31 to 36 as he was from 24 to 29.

The problem is trying to find an adequate replacement. The other top free-agent starters next offseason are likely to be Scherzer, whose agent, Scott Boras, undoubtedly will aim high, plus right-handers James Shields and Justin Masterson.

Shields had success in the AL East with the Rays, but he'€™s two years older than Lester. Masterson began his career with the Red Sox, but isn'€™t nearly in Lester's class. Lefty David Price, the prize of the following free-agent class, is almost certain to dwarf Lester'€™s dollars.

While free agency isn'€™t the only way to acquire an elite starting pitcher, the other methods are just as problematic. The Sox's farm system is on the verge of producing another wave of pitching prospects, but none is certain to develop into a top-of-the-rotation starter. Trading for the next Lester is even more of a longshot; few teams are willing to give up such an animal.

Which isn'€™t to say Lester is indispensable: Righty Clay Buchholz and lefty Felix Doubront are under club control through 2017, righty John Lackey through '15. But suffice it to say the Sox likely would be a whole lot better with their ace lefty than without him.

So, get it done: Five years, $110 million with a vesting option for a sixth year that could increase the value to six years, $135 million.

Not so difficult. Not so difficult at all.

Play FOX Fantasy Baseball Commissioner MLB Game