Oct 28, 2013; St. Louis, MO, USA; Boston Red Sox starting pitcher Jon Lester throws a pitch against the St. Louis Cardinals in the first inning during game five of the MLB baseball World Series at Busch Stadium. Mandatory Credit: Eileen Blass-USA TODAY Sports

Red Sox Should Not Sign Jon Lester To Big Money Extension


Oct 28, 2013; St. Louis, MO, USA; Boston Red Sox starting pitcher Jon Lester throws a pitch against the St. Louis Cardinals in the first inning during game five of the MLB baseball World Series at Busch Stadium. Mandatory Credit: Eileen Blass-USA TODAY Sports

Jon Lester is a good pitcher. Jon Lester had a good 2013 season and a great 2013 postseason, leading the Red Sox to the World Championship as the team’s #1 starter. It’s easy to get emotionally attached to players like Lester, as he has been a part of the team since 2006 and has an excellent backstory of overcoming adversity. However, despite Lester being one of the best left-handed starters in baseball right now, the Red Sox should not sign him to a long, expensive contract extension.

Lester had a strong season both on the surface and peripherally, as he posted a 3.75 ERA with a 3.59 FIP and 2.64 K/BB. However, it’s easy to forget that a second half surge was the only thing preventing Lester from having his second consecutive season with an ERA over 4.50; his ERA at the All-Star Break was 4.58 after posting a 4.82 mark in 2012. That’s not to say that Lester got lucky in the second half, where he posted a superb 2.57 ERA at the forefront Boston’s rotation. I think that Lester is a good pitcher, and hopefully the second half was a return to form rather than an aberration, but it’s tough to say.

Lester’s second half was benefited greatly by a severe drop in his home runs allowed per nine innings. After allowing an admittedly high 1.07 in the first half, he allowed only 0.41 per nine in the second half. Lester’s career rate is 0.84 HR/9– much closer to the first number than the second. Given that none of his other statistics changed all that much, save for his walk rate, which decreased from 3.22 to 2.26– dropping from a number close to his career norm to one well below it.

Overall, it’s a tough call with Lester. He has had his ups and downs over the last few years, and it’s clear that when Lester is on, he is dominant, but when he is off, he is incredibly hittable. Lester, going into his age 30 season, is soon going to have to deal with the inevitable dropping of velocity on his fastball and the dulling of his off-speed pitches.

With that being said, Lester is a good pitcher but is really more of a #2 or #3 starter than the ace he will likely be paid to be. A few contract projections for Lester have been 5 years/$100 million and 6 years/$120 million. Steamer and Oliver project Lester’s to post ERA’s of 3.90 and 3.93 respectively in 2014, making him a perfectly serviceable starting pitcher, especially as a lefty, but not a pitcher worth $20 million per year. I’d still like to see the Red Sox extend Lester, but not at the prices that I’ve seen thrown around.

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  • John Fahrer

    It really will depend on what Lester thinks is fair and/or what the club is willing to offer. If Lester’s willing to take a discount like Pedroia and it’s 5 $75 million or 6 $90 million, that’s a no-brainer.

    Another factor will be the rest of the current staff and the progression of the prospects. If Doubront lowers that ERA and WHIP and boosts his innings total and Buchholz can make 30 starts, then the club will probably feel less pressure to throw big money at a pitcher with a lot of miles on his arm.

    • Conor Duffy

      I completely agree. If it’s 5/$75, then he should absolutely be extended. The numbers that I’ve seen thrown around so far have been closer to 5/$100 though. I’m not saying that they shouldn’t extend him, just that they shouldn’t sign him to a huge contract.

  • Willy

    I did an article for ChowderAndChampions about Lester and I basically said if Lester wouldnt except less than the expected $20M or more a year type deal than the Sox should trade him & reap the rewards.

    • Michael Macaulay-Birks

      Exactly what “rewards” would you expect for 1 year of Lester? Just curious

      • Willy

        I would suggest reading my article on Chowder and Champions but coming off his championship performances I would say they could get a Shields type return, perhaps even bettter depending on if Ben would be willing to “Sweeten” the deal like the Rays did.

        • Aaron Somers

          Shields had two full years of control left, where Lester would only have one. The return won’t be of equal value by any means.

          • Willy

            Ask yourself, is there more value in 1 extra year OR a LHSP that was directly responsible in helping his team win a Championship? IMO Lester has even more value, especially to a team that is looking for a SP to help them win a Championship. Teams like LAD, ARZ, STL would pay dearly for Lester.

          • Willy

            Ask yourself, is there more value in 1 extra year OR a LHSP that was directly responsible in helping his team win a Championship? IMO Lester has even more value, especially to a team that is looking for a SP to help them win a Championship. Teams like LAD, ARZ, STL would pay dearly for Lester.

          • Aaron Somers

            Years of control will always trump playoff experience. I get your point Willy, but I have to disagree with you here. No team is going to give up more for a guy who’s been on winning teams instead of the guy who’s going to be under team control for longer. It’s just not going to happen. It’s not the way the game works.

          • Willy

            I can understand thinking that way, especially if Lester had an agent like Boras but he doesnt. I dont see a team willing to pay, not being able to sign him. Like I said, A team like the 3 I mentioned that really want to win a Championship, see that Lester can dominate against competition in the biggest of games, would be willing to give a Lot.

          • Aaron Somers

            So the LA Dodgers would be willing to pay a hefty sum to acquire Lester and then re-sign him. That’s what you’re saying.

            The Dodgers already have four expensive starters in their rotation in Kershaw, Greinke, Ryu, and Haren. Plus they’re looking at Beckett and Billingsley (neither of whom are cheap) battling for the 5th spot once healthy. The team also has a pending contract extension with Kershaw, which is going to be one of the largest contracts in MLB history given the caliber of pitcher he is. To top everything else off the team doesn’t have much depth to their farm system, at least not in terms of top-level talent that they are willing to part with.

            You still think the Dodgers might go after Lester just because he’s “proven he can help win”?

          • Willy

            Yes. Have you not seen/heard Magic Johnson’s press conferences…? He has said money is no object. No one thought the Sox would be able to unload both Beckett & CC but Ben did business with the Dodgers and they willingly took on payroll, gave us money and propsects too. And the Dodgers still have some good prospects with which to deal. Also, they are only 1 of 3 teams I mentioned. There could also be more than the 3.

          • Aaron Somers

            I still disagree, but it’s irrelevant because I see no reason why the Sox would be looking to move Lester right now. If they make the decision not to re-sign him then they are far more likely to wait until after the season, make a qualifying offer, and collect the draft pick when he signs elsewhere.

          • Willy

            I could see them doing that if Lester were a position player but not with him being a pitcher. There is far more value in trading him now, getting good prospects or players (which ever they prefer) than let him walk away and get a suplemental draft pick that you can only hope will turn into a good player. Pitchers have too much value to just let them walk away and be satisfied with a draft pick. Also, the Sox have needs, as good as their prospect pool is (and its very good) they lack depth in Outfielders and 1st basemen, hard to build those up through 1 draft, easier to get in trade.

  • Rick M

    What I would require as an agent would be years. I’d look for at least five and certainly more than say a Tim Lincecum gets (2/35) in yearly average compensation. Maybe even an option year? What Lester provides is remarkable consistency in starts and innings – certainly superior to the enigmatic and fragile Buchholz. As an agent my strike price would certainly be in the 5/100M range with a higher asking price. All within market.

    With the Red Sox the interest will be dependent upon player development. Consider also that both Peavy and Dempster could be gone after 2014. With Lester you would have that staff anchor for the next group of prospects.

    If Lester gets his usual 30+ starts and 200 innings while his starts result in team wins it would be difficult for Sox to say no.