Jon Lester, Red Sox Both Still Interested In Extension

Jon Lester is due to become a free agent after the season, but both he and the Red Sox hope an extension is in the works, CBS Sports' Jon Heyman writes. And with Lester declaring that "I don't like change" and Red Sox brass declaring their strong interest in keeping him, Heyman writes, the odds are that an extension will get done. The Red Sox picked up their $13MM club option on Lester for 2014, and Lester would surely get a hefty raise on that total in an extension. Despite both parties' interest in completing a deal, however, it's not a given that a contract will get done before spring training ends. "I'd like to get it done down here," Lester says. "But it's going to be a tedious process." Yesterday, Lester's agents, Sam and Seth Levinson, arrived in Red Sox camp, although the reasons are unclear.

In negotiations between Lester and the Red Sox, an obvious starting point would be Homer Bailey's recent contract with the Reds. Like Lester, Bailey was due to become a free agent following the 2014 season. The two were fairly similar in value in 2013. Lester, at 30, is two years older than Bailey, but likely would receive somewhat more per year due to his better career performance. Bailey received six years and $105MM, with a mutual option for 2020.

31 Responses to Jon Lester, Red Sox Both Still Interested In Extension Leave a Reply

  1. Cyyoung 1 year ago

    5 years 115 million. He’ll want more than Tanaka.

  2. Bill Sipe 1 year ago

    I like Lester but would rather that they go with kids

    • dc21892 1 year ago

      They’re going to want Lester around for when the kids come up. Having him back for 4-5 more years wouldn’t be a terrible idea. He’s a good pitcher. I’m thinking 5/90 gets it done. He wants to be back, they want him around, it’s kind of a win win.

      • stl_cards16 1 year ago

        Completely agree. When you are bringing up young pitchers they can’t be counted on to come up and throw 200+ quality innings and a contending team definitely needs that at the top of a rotation. It’s the same situation the Cardinals were in with Wainwright last off-season.

      • Bill Sipe 1 year ago

        I don’t completely disagree but I’m just feeling that $18 million a year can be spent better.

        • carlos zepeda 1 year ago

          He deserves it. besides ortiz. he won us the world series. If the redsox plan to be in the playoffs for years to come why not have a guy who performs best in those moments. (1.98 ERA in 11 career postseason starts) and with guys like nolasco getting huge contracts and have not proven anything it is a no brainer to me to sign a Lester especially for a home discount. Sign him ASAP

        • Michael 1 year ago

          Ironically, if you look at what’s been happening in the past year or two, $18 mil/year will seem like a steal by 2016.

          • Bill Sipe 1 year ago

            You’re probably right…OK but hope 5/100 is the most that they do! Would make Pedroia’s decision look bad though.

  3. Elston Howard 1 year ago

    I’m guessing 5/100 . I think their plan will be keep Lester, Bucholtz, and Doubront – and replace Peavy, then Lackey with youth.

    • Bill Sipe 1 year ago

      After talking and considering the points in here- this makes sense to me…

  4. Unless he completely falls apart, a five year deal would put Lester as one of the all time great Red Sox pitchers. He can become number 4 on the all time wins list within two years. Lester will be set for life wherever he goes, but there aren’t many places other than Boston where he has a chance to be on the leaderboard of a storied franchise. I really hope Lester stays.

  5. UltimateYankeeFan 1 year ago

    Even a team friendly deal is likely to cost the Red Sox 5 years / $110 to $115MM total and probably a 6th year option at $25MM. Overall I would be very surprised if even a team friendly deal didn’t cost the Sox about $140MM over 6 years with that option. Considering he’ll only be 31 in January 2015 I don’t see a 6 year deal as an issue. It would be a good deal for Lester and a very good deal for the Sox as long as Lester doesn’t go into some sort of funk during the contract.

    • Bill Sipe 1 year ago

      Well. ya that’s something the Yankees would do… Doubt the Red Sox will go more than 5/100…we’ll see soon I bet.

      • UltimateYankeeFan 1 year ago

        I guess then the Red Sox didn’t sign Pedroia because his deal was for more then 5 years guaranteed.

        • Bill Sipe 1 year ago

          I was talking about the amount of $25 million not so much the term… Pedroia’s average annual is less than $14M.

          • UltimateYankeeFan 1 year ago

            The $25MM I mentioned as the option is about 6 years down the road. taking into account MLB’s inflation rate that’s not a lot of money 6 years down the road.

            BTW, your earlier reply specifically said “Doubt the Red Sox will go more than 5/100..” That sounds to me like you don’t believe the Sox will go past 5 years. I just think considering Bailey just signed a 6 year deal (2014 through 2019) with a 7th year mutual option that for Lester 6 years (including that option year I mentioned) still is a very friendly team deal.

            My proposal comes to:
            5 years guaranteed @ $110 to $115MM = $22 or $23MM per
            factoring in the option year I mentioned brings the total AAV to $22.5MM or $23.3MM per. Not an exorbitant salary by any means according to MLB standards for a front line starter.

            Like you said though we’ll find out at some point.

          • NOLASoxFan 1 year ago

            Homer Bailey is two years younger than Lester.

          • UltimateYankeeFan 1 year ago

            …and not as good as Lester. BTW, the fact that Bailey is younger is why I suggested 5 guaranteed years and 1 option year instead of the 6 guaranteed and 1 option year Bailey signed for. BTW, Bailey pitches for the small market Reds in the NL Central and as you know Lester for the rich AL East Red Sox.

          • Hugh Langin 1 year ago

            options are not counted into the calculation for the AAV of a contract. Only guaranteed money is counted, if there is a buyout value associated with the option that would be counted…but not the option.

        • NOLASoxFan 1 year ago

          Big difference between an aging infielder and an aging SP.

          • Bill Sipe 1 year ago

            I agree- guess I’m saying 5/100 makes sense to me but the Yankees can sign him for what UltimateYankeeFan is talking.

          • NOLASoxFan 1 year ago

            I’m agreeing with you. Everything else is sarcasm.

      • NOLASoxFan 1 year ago

        The Yankees would also throw in a 7th year vesting option, a bunch of easily attainable bonuses, and an opt out after three years in case he wanted to renegotiate for more money.
        I’m with you in guessing the Sox don’t go much over $100M for five years.

        • UltimateYankeeFan 1 year ago

          My friend maybe at some point Sox fans like yourself will put aside their “inferiority complex” of the Yankees and Yankees fans. This blog and my comment more specifically was about what I felt was a “fair” deal for both the Lester and the Red Sox. Sorry you couldn’t see that from my initial comment and make your reply in that light. .

  6. start_wearing_purple
    start_wearing_purple 1 year ago

    The Sox always sign extensions after the season starts in order to save on luxury tax. Any announcement on Lester will be early April. My guess is a 6 year deal for $18M a year with a mutual option and high buyout.

    • UltimateYankeeFan 1 year ago

      Since Lester’s 2014 salary is already set there is no luxury tax implication for the Red Sox for 2014 if they announce a new deal for Lester starting in 2015. It would only be an issue if Lester’s 2014 salary was yet to be determined.

      • start_wearing_purple
        start_wearing_purple 1 year ago

        Luxury tax is based on a player’s average salary, not yearly. Thus why the Sox always sign extensions during the season. If Lester signs an extension before the season starts then the luxury tax line for the Sox changes.

        • Booker Smith 1 year ago

          Actually, if they make the deal start in 2015, then they don’t have to worry about the luxury tax. His 2014 salary is already set.

          • start_wearing_purple
            start_wearing_purple 1 year ago

            Ah, ok. Thanks. Thought it was something else.

          • Fritz 1 year ago


            The salaries you mentioned are too high. Lester will take a hometown discount. If you see what Pedroia got (he probably took like 4-6 million a year less per year) my guess is that Lester hometown discount contract will be 5/90 or 6/105 maximum. We know the Yankees player dont do those kind of things, they take top dollar. Period. thats not bashing its a fact. I think those numbers you mentioned are just part of your wishful thinking what Lester will hopefully get. I bet you are wrong.

          • UltimateYankeeFan 1 year ago

            Sorry my friend but you are mistaken about my intention. Lester’s option that was already picked up for this year is for $13MM. You honestly believe that Lester is going to sign a 5 year deal for $90MM = $18MM AAV. A $5MM per year increase over his current salary.OR 6 years / $105MM = $17.5MM AAV a $4.5MM increase per year. Personally I think that’s wishful thinking or dreaming.

            If that’s all he gets he should fire his agent.

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