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What Matt Cain’s contract means to Jon Lester and the Red Sox

04.02.12 at 4:51 pm ET

San Francisco pitcher Matt Cain is much richer man today than he was yesterday, signing a five-year, $112.5 million extension with the Giants (with a $21 club/vesting option for 2018). So the 27-year-old will be making $20 million a year from 2013-17.

It was a also a good day for Jon Lester.

The Red Sox lefty’s contract isn’t most likely up until after the 2014 season (the Sox hold a $13 club option for ’14 they surely will pick up). He is in the midst of a five-year deal for $30 million he signed March 15, 2009. But, assuming Lester continues down his current career path, when he does become eligible, the stakes just got a whole lot higher.

(It should be noted that Lester recently switched agents, going with Sam and Seth Levinson at ACES after previously partnering with SFX.)

Lester’s track record is trending toward a significant pay day, which would seem to be even more exorbitant now that Cain has inked his record deal for a right-handed pitcher. Only three pitchers in Major League Baseball have won 15 games for four consecutive seasons — CC Sabathia, Roy Halladay and Lester. The Sox’ Opening Day starter while averaging more than 200 innings per season and totaling a 3.33 ERA over the past four years. They are feats no other American League East pitcher has managed with the exception of Sabathia.

Lester, who was born in the same year as Cain, not only has the kind of numbers that match-up favorably to the San Francisco starter, but will still be just 30 when free agency rolls around. Up until recently, such scenarios as what awaits Lester might suggest a deal in the vicinity of an AAV of around $17 million (see Josh Beckett, John Lackey, Jered Weaver). But now you have Cain, Cliff Lee, Tim Lincecum and Roy Halladay, all of whom are averaging more than $20 million per season.

Simply put, if Lester keeps being the Lester we’ve witnessed the last four seasons, the Red Sox will easily have to count on another $20-million-plus player on their roster if they want to keep the lefty.

Such days as today aren’t good ones for the Red Sox. Last year, Matt Kemp set an uncomfortable bar for Jacoby Ellsbury (who is up after the ’13 season). Cain did the same for Lester. And when Robinson Cano inks his new deal (he is in the last year of a four-year contract), Dustin Pedroia will have his jumping off point. That could be five players on one roster (Carl Crawford, Adrian Gonzalez, Lester, Ellsbury and Pedroia) potentially at $20 million or more if they were all to re-sign.

It makes the contract of Clay Buchholz, which has the pitcher under the control of the team through ’17 while never being paid more than $13.5 million, so important.

For a team that will — like the Yankees — be trying to stay under $189 million by ’14 due to new CBA rules (revenue sharing rebates, chance to reset luxury tax threshold penalty percentage), the likelihood of keeping the core together is looking more and more non-existent. Monday, thanks to Cain, the Red Sox were slapped with that reality once again.

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