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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
By Rob Bradford

Jon Lester will make the Opening Day start for the Red Sox on April 5. (AP)

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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  • WindupTheRondo09

    Seriously, the owners & Theo have so severely mismanaged their money over the last few years (i.e. Lack-adaisical, history’s worst PI’s resulting in an inflated Crawford contract), that they won’t be able to afford to keep their most talented players like Lester.  As his 2008-2011 statistical averages show (16 W, 3.33 ERA 32 GS, 203 IP, 196 K), he is the epitome of consistency and his payday is coming.  One better hope the Brick Builders find a way to keep him in town.

  • innovator

    Cain was just overpaid…He’s no more than a 16 million dollar pitcher,and has an occasional sore arm to boot….Lester should be a 5 year/90 million dollar pitcher at the most…..Ellsbury isn’t Matt Kemp,nor will he ever will be…..I’ve been yapping about moving Crawford since the middle of last year…kick in 40 mil with his contract just to move him…Excersize lackey’s extra year option for 2015 at the league minnimumm,so it dumbs down his yearly hit to 11.25 mil per year,and send him packing while eating about 15 million of that….Lets clean up these Theo Fiasco’s so we can keep our core…Pedroia,Lester and Ellsbury should all be somewhere between 17-18 mil per year maxx,period!!!

  • Shennessey

    Sox are doomed for years to come with all these huge contracts they have and what will be coming up. Lester has to have had the dumbest agent in baseball. His next deal will not be the bargain basement variety, 20 million to start for 5 to 7 years. Pedy will get 17 to start for 5 to 7 years. And lets not forget Ellsbury 20 million is the starting point. He will look good in pinstripes. You can’t expect Ellsbury to take anything less then what Crawford is getting since he is a much better player. And Pedy is one of the best in the game at second . The one thing the Yankees have going for them is they are loaded at the minor league level with starting pitching, Jeter will be gone soon, Swisher is in the last year, Granderson will be there another couple of years and then they will replace him with Ellsbury. The sox will have to replace there whole outfield. It might be another 86 years before the Sox win anything again

  • Nomisnala

    The owners can afford it.  Your owner cried poverty when he owned the Marlins, and then went ahead and bought the RedSox for 625 million.   What is a million here, and million there to these guys?

  • Dijjfy

    *their

  • sev

    recently the sox farm system was ranked 9th and I wanna say the yankees was like 13th or 14th.  Yankees do have more starting pitcher depth that will be ready sooner, but I believe the sox have more position players, and have had better drafts recently, meaning the younger guys that won’t contribute for a while.  However, our core will end around the time these guys are ready and some of the older ones have already been incorporated…lavarnway… iglesias…alex wilson…tazawa….middlebrooks, but like I said that doesn’t count the real young guns in single and double. 

  • sev

    i also thought lester switched agencies because his agent went to ACES, which does not necessarily mean he’s is chasing the money, as he probably just felt comfortable with having the same agent, who a lot of times can be friends with these guys.  Still think his actually agent is the same.  Didn’t sound that way in this article

  • Anonymous

    It is humorous that sports writers spend so much of their energy and resources worrying over why teams spend as the do, rather than what they do on the field.  The irony is most baseball players and serious baseball fans ignore what they have to say, recognizing, that it is mostly meaningless, drivel.  Only the occasional fan, or totally naive reader gives any credence to what these guys have to say.  

  • Anonymous

    It is humorous that sports writers spend so much of their energy and resources worrying over why teams spend as the do, rather than what they do on the field.  The irony is most baseball players and serious baseball fans ignore what they have to say, recognizing, that it is mostly meaningless, drivel.  Only the occasional fan, or totally naive reader gives any credence to what these guys have to say.  

  • cw007929

    I hate to say it, but I completely agree. There is no way we resign Ells, Lester, and Pede. The Red Sox need to let maybe one (more likely two) of them go, and need to continue to develop talent of the likes of Lester, Ells, Dustin. The Sox have some nice talent coming up in the next few years, but you look at the Rays. They are literally, at the bottom of the “food chain” as far as income. Everyone knows about their SP, but do you realize, they could lose Price, their ace, and not lose a beat? Their minor league pitching is that stacked! That’s what the Sox need to become.
    But as fare as these contracts rising at such a rate…bottom line is, this players association is getting ridiculous. I know there is inflation, but when a #2 starter is getting $20mm per year, something is extremely wrong. I know it’s probably way too late and risky (strikes), but MLB really needs to limit the players association’s power.    

  • Bill in CT

    The Redsox need to quiet crying this poverty crap. We have to pay high ticket prices…they need to pay Lester, Pedroia and Ellsbury. If they don’t they are full of s*&t and do not need to blame it on the Crawford signing. Straight B.S.

  • Midolo1

    Seriously. You are starting already about a contract that is two years away. The world would be better off without you sportswriters

  • Craig

    I see Lester and Pedy staying they are the core of the team and are character guys. Pedy is the heart and soul of this team no way he doesnt get a contract. Elsbury should have got the deal Crawford got. That was another huge Theo mistake. He was a disaster on free agents. He did trades ok and he was good with the draft and farm system but he has left the payroll and mess and then ran out of town. I do not think too much of him for that.

  • Angreejohnee

    Here’s how its going to play out…the Sox will low ball Lester, his agent will refuse and then Lucchino will open his big yap, say something insulting and Lester will walk
    The Sox brass have f’d up this team beyond repair and Cherington is so way over his head with the likes of BobbyV running the field mgmt

  • Anonymous

    If  Welker has a great year he will again be franchized,but thats not likely in 2012 because the Pats have many more offensive weapons

  • Charlie

    Hernandez and Vollmer will get paid! I’m not sold on Chung. 

  • Charlie

    And don’t tell me you can’t pay 2 TE! If you can pay 1 WR top dollar and 1 TE top dollar…you can pay 2 TE! Our offense goes through those 2! 

  • http://profiles.yahoo.com/u/ZVFM2HRNC5CTO2OUXD4XTX65O4 Dennis

     To protect their investment, the Pats have to “sit on” Gronk. He seems the type who could get into off field trouble real fast. 

  • Anonymous

    Hernandez, no question. Not sold on McCourty yet, Sea-Bass’ back scares me, SPikes isn’t as valuable as Aaron’s versatility, and I think Gregory’s signing will cut into Pa-Chung’s playing time.

  • http://www.americaunwrapped.com/ Gayzell

    It’ll be a phenomenal event, if it goes as planned. But right now, I’m stressing.”

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