Extending Lester

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The Talented Allen Ripley

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Johnston & Flynn were filling in for Toucher & Rich this morning on 98.5, and during the show they spoke with Peter Abraham regarding a possible Lester extension, then discussed the topic themselves for a while afterwards. Abraham said that the Sox will definitely talk to Lester about it in the offseason (Cherington's confirmed this), and that Lester is open to the possibility, as per this interview with WEEI:
 
"We’ll decide to sit down and talk," Lester said on WEEI. "I assume it would be some form of communication, I would imagine hopefully in Spring Training. Obviously, Boston is my home. This is all I’ve known, all I’ve come accustomed to and all I want to know. My family enjoys it up there I enjoy it up there. There are a lot of factors in it.
 
"But at the same time, there’s a business side of it. Kind of like Jacoby, I have to do what’s best for me and same thing with the Red Sox. Sometimes you have to part ways, hopefully that’s not the case when it comes down to us here in the future."
 
He already signed an extension in 2009, so he's shown in the past that he's willing to forgo top dollar for security (unlike Paps and Ellsbury), but that may be the very reason he tests the market after this year: he gave the Sox their hometown discount and he's now financially set for life regardless of what happens now (security is no longer an issue), so he might as well go for top dollar. He may simply want to see what the market will bear, if only to drive up any Red Sox offer that he ultimately plans to accept.
 
Lester's not a true ace, but few pitchers are. He's the next best thing, a #1A, and his postseason track record will surely be a factor in any contract negotiations. The baseline seems to be Cole Hamels' contract, per the Herald:
 
During his daily winter meetings briefing with reporters Tuesday, Red Sox general manager Ben Cherington said the club intends to broach the subject of a contract extension for playoff ace Jon Lester later in the offseason or in spring training.
 
And if the sides are seeking a basis of comparison for their negotiations, they need only look to the Philadelphia Phillies' dealings with Cole Hamels.
 
Hamels and Lester have followed almost the same career path, their similarities extending far beyond their status as left-handed pitchers with strong postseason pedigrees. Hamels is only 12 days older than Lester and made his major league debut one month earlier in the 2006 season. Hamels is 99-74 with a 3.38 ERA and 1,509 strikeouts in 1,596.2 career innings; Lester is 100-56 with a 3.76 ERA and 1,237 strikeouts in 1,376.1 career innings. Hamels went 4-0 with a 1.80 ERA en route to leading the Phillies to the 2008 World Series title; Lester went 4-1 with a 1.56 ERA en route to leading the Red Sox to the 2013 World Series title.
 
Then, there's this: In January 2009, three seasons into his major league career and a few months after the Phillies won the crown, Hamels signed a team-friendly, three-year contract extension that essentially bought out his arbitration years for $20.5 million. Two months later, three seasons into his major league career and two years after winning the clinching game of the 2007 World Series, Lester agreed to a team-friendly, five-year contract extension worth $30 million.
 
So, with Lester set to turn 30 next month and free agency looming at the conclusion of next season, he can reasonably seek a contract that resembles the six-year, $144 million deal that Hamels signed with the Phillies in July 2012, when he was 28 and facing free agency.
 
Is this a valid comp? Discuss.
 

mauf

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Lester and Hamels are both durable lefties. The similarities end there.
 
Jon Lester's SIERA was 3.97 in 2013 and 3.94 in 2012. Hamels has never had a single-season SIERA higher than 3.66, and his SIERAs were 3.26 and 3.03 in the two full seasons prior to signing his extension.
 
Also, Lester and Hamels are almost exactly the same age, which means Hamels was roughly a year and a half younger than Lester is now when he inked his current deal.
 
Either Scott Lauber (the Herald writer) is an idiot, or he's parroting something that Lester's agent told him. Or, possibly, both.
 

glennhoffmania

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Hamels is a valid comp in the sense that I think the two pitchers are of similar value.  But the fact that Philly overpaid Hamels doesn't mean Lester is worth that deal.  Here is the list of pitchers who are paid more than Hamels based on AAV:
 
Verlander
Felix
Greinke
Sabathia
 
And Hamels is only $1.7m less than Verlander.  Is Lester in the same class as those 4 pitchers?  I would say no.
 

Ed Hillel

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My thought with Lester has been something in the 5/100, maybe 5/110 range, but my guess is that he'll want more years. As much as I like Lester, I'm not sure I'd want to go much beyond that, unless the AAV is reduced, or the years are options, especially since his 10/5 rights will kick in. It's not an easy decision, but if his desire is to truly get top dollar, I would assume he's gone. Someone (Yankees) will go 7-8 years, and I can't justify making that committment in my mind.
 

mauf

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I think SoSH overestimates how much Jon Lester would command on the open market. Objectively, he isn't as valuable as Zack Greinke, who got 6/147 last winter. If Lester were a free agent now, I'd be shocked if he did better than 6/120. 
 
If Lester is willing to discount that to 6/100 (i.e., a 5/87 extension on top of the $13mm he's owed for 2014, presumably with a big signing bonus to get cash in his hands immediately), I think that makes sense. If he wants more than that, let him test the market.
 
If the Hamels comp is coming from Lester's agent, that doesn't bode well for an extension getting done, but I don't want to assume there's anything to that report -- it might just be ill-informed speculation from a dumb-ass Herald writer (but I repeat myself).
 

Minneapolis Millers

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I'm sure the Sox are hoping for something more in the Jered Weaver, I-want-to-stay-here contract range than the lofty Hamels deal.  That's a fair deal, imo, though I'm sure he could get more on the open market. 
 
I just wish Lester had mentioned Pedey in that interview and not Ellsbury!
 

Toe Nash

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Before the playoffs I would have said that Lester wasn't worth extending. His durability is great and I know he was unlucky in 2012 but he was still not up to his former stuff (4.11 FIP) and was a big question mark.
 
Then he was fantastic on the biggest stage. It's very tempting to overvalue that but I don't think much has changed. Lester's K rate has been on a steady decline since 2009 even as the league K rate climbs to unprecedented levels. If he wants to take a discount to stay then sure but as noted he doesn't have much reason to do so. With the pitching depth in the system I'd let some other team take the risk on paying Lester market rate.
 

jimbobim

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I think its unrealistic to say he won't get at least 20 a year for for probably 6. On this market or next years market I think he would easily clear that. If it takes seven years the Sox probably respond by raising the AAV. 
 

Curt S Loew

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Minneapolis Millers said:
I'm sure the Sox are hoping for something more in the Jered Weaver, I-want-to-stay-here contract range than the lofty Hamels deal.  That's a fair deal, imo, though I'm sure he could get more on the open market. 
 
I just wish Lester had mentioned Pedey in that interview and not Ellsbury!
You probably should have read it:
 
 
"If you sign a deal before you become a free agent, you’re probably going to leave money on the table," Lester said. "Like Pedey, he left a ton of money on the table. But this is where he wanted to be the rest of his career and he sacrificed to become a Red Sox. I think when you get down at that point, you have to weigh those things and that’s something you have to sit down and you have to decide.
"We’ll hope for talks in the next couple months."
 

C4CRVT

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If Lester is going to demand 20/year, I would guess he's gone. My guess is that the FO is going to try to lock him up for 16-18/year on a 4-5 year extension. If he likes that, he'll stay. If not, he'll go.
 

bankshot1

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Given the nature of the FA market, (Ellsbury, Cano getting way more than pundits figured), the additional TV money teams have to spend, and the never ending demand for good LH starting pitching, IMO it is unrealistic to assume that Lester, who is a 1 1/2-2, will sign anything significantly under market. IMO, a 1 1/2LH, with a nice resume, pitching in the best division in baseball, and having post-season success, against 1s, has all the leverage.  IMO his market starts at 6/120-130. 
 

rembrat

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Toe Nash said:
Before the playoffs I would have said that Lester wasn't worth extending. His durability is great and I know he was unlucky in 2012 but he was still not up to his former stuff (4.11 FIP) and was a big question mark.
 
Then he was fantastic on the biggest stage. It's very tempting to overvalue that but I don't think much has changed. Lester's K rate has been on a steady decline since 2009 even as the league K rate climbs to unprecedented levels. If he wants to take a discount to stay then sure but as noted he doesn't have much reason to do so. With the pitching depth in the system I'd let some other team take the risk on paying Lester market rate.
 
I think this line of thinking is nuts. Who in the system projects to be Jon Lester?
 
I've wanted him extended for a few years now. I hope they get something done early in the season ala Josh Beckett. Come to him with 6/$120MM in April and be done with it.
 

jimbobim

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Agreed bankshot1. Analytically and in a vacuum Lester is probably a 16-18 mill dollar a year pitcher. Before his beast second half of the year he was a very dicy extension candidate. 
 
After his second half and playoffs that decision has become either tougher or easier in regards to whether you think that's the Jon Lester your going to get more often then not for the next 3-4 years. 
 
Bottom line is without adding another frontline pitcher letting Lester leave would be placing a big bet on our prospect pile turning out gold. I imagine thats the rosy expectation for Henry Owens. I think they'll find a middle ground north of 100 million, but he's going to compare his deal directly to Pedroia's.  
 

Stanley Steamer

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My first thought was that 4/80 would be a good starting point for the team, but after reading the above, I agree that may not be realistic. Still, I'd be reluctant to add more than 4-5 years to his upcoming option year. Obviously, we all saw how Jon was able to turn the corner late this year, yet it's clear how fine the margin is between very hittable pitcher and shut-down ace. We'll likely see both these pitchers over the course of the deal, so if a discount is in the offing, an AAV of 20M for less than 6 years may be about right.
 

Snodgrass'Muff

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With the pitching depth in the system I'd let some other team take the risk on paying Lester market rate.


This is only a small part of your point but I thought it was worth pulling out. The starting pitching depth on the farm is as good as I've ever seen it, and may be the best in baseball right now, but I'm not sure that it's enough to be gun shy about extending Lester. After 2014 the team will have Peavy and Dempster off the payroll and both are old enough that bringing them back might not be a good use of resources. In 2015 Lackey's contract comes to an end. At that point they will have Clay Buchholz and Felix Doubront under control, whatever pans out on the farm and the free agent market.

Clay is incredibly talented but hasn't been able to stay healthy. Felix is a great back of the rotation option but I don't want him anchoring the staff. Extending Lester means buying into a known commodity, getting out ahead of a huge amount of turn over that's coming and minimizes the amount of competing in the free agent market they'll have to do to fill out the roster in the coming years.

I think it makes a lot of sense to push hard to get that done this winter or spring to make sure they have 2.5 quality starting pitchers locked up so that if the farm system doesn't produce 3 major league quality pitchers (which it very possibly won't), they don't end up having to overpay for a mediocre or risky free agent.
 

Minneapolis Millers

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Purist - thanks.  I can't read every link, b/c most sports sites get blocked at my work (not Sosh, for some reason).
 
Paying Lester like he's a top 10 pitcher in baseball is dicey.  He seems to have a hard time maintaining his mechanics and has been significantly less consistent than guys like Cliff Lee.  I agree that our numerous, good but not spectacular pitching prospects should not preclude locking up an "ace."  I'm just not sure that Lester is a guy you shell out $20M+ per for 6+ years, his last two months notwithstanding.
 

Toe Nash

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rembrat said:
 
I think this line of thinking is nuts. Who in the system projects to be Jon Lester?
 
I've wanted him extended for a few years now. I hope they get something done early in the season ala Josh Beckett. Come to him with 6/$120MM in April and be done with it.
Yeah that Beckett extension was great. 
 
I dunno, they have 5 SP in MLB.com's top 100 and I think other rankings concur. It's inconceivable that one or two of those guys breaks through?
 
You also shouldn't ask who projects to be Lester, but rather who Lester projects to be. I don't think we're getting the 2009-10 guy back. If he is closer to 2012 than 2013 in the next five years that is easier to replace. Even in 2013 he was 41st in FIP among qualified MLB SP. In 2012 he was 58th and in 2011 he was 53rd. The durability is to his credit but this doesn't seem like someone to break the bank for if his name was John Smith. Again the playoffs should count in his favor, but how much?
 

snowmanny

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His final numbers for this year were 19-9 with a 3.45ERA 248IP 8.3K/9  3.0BB/9 WHIP1.28

With the exception of 2012 he has been very consistently effective, and he has made at least 31 starts over the past six seasons.

We all know who is signing him if he doesn't get an extension.

To me this has always been the number one priority of this off-season.
 

Toe Nash

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Snodgrass'Muff said:
This is only a small part of your point but I thought it was worth pulling out. The starting pitching depth on the farm is as good as I've ever seen it, and may be the best in baseball right now, but I'm not sure that it's enough to be gun shy about extending Lester. After 2014 the team will have Peavy and Dempster off the payroll and both are old enough that bringing them back might not be a good use of resources. In 2015 Lackey's contract comes to an end. At that point they will have Clay Buchholz and Felix Doubront under control, whatever pans out on the farm and the free agent market.

Clay is incredibly talented but hasn't been able to stay healthy. Felix is a great back of the rotation option but I don't want him anchoring the staff. Extending Lester means buying into a known commodity, getting out ahead of a huge amount of turn over that's coming and minimizes the amount of competing in the free agent market they'll have to do to fill out the roster in the coming years.

I think it makes a lot of sense to push hard to get that done this winter or spring to make sure they have 2.5 quality starting pitchers locked up so that if the farm system doesn't produce 3 major league quality pitchers (which it very possibly won't), they don't end up having to overpay for a mediocre or risky free agent.
This is a great response and I can definitely see the benefit in having a guy you can be pretty sure will take the mound and be above-average and at times, excellent. I hope it doesn't seem like I want Lester gone; just that I'd put the price lower than 6/120 and if he's set on getting market rate I don't see it as a good idea.
 

glennhoffmania

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Here is a list of potential free agents next year.
 
Brett Anderson (27) - $12MM club option with a $1.5MM buyout
Homer Bailey (29)
Josh Beckett (35)
Chad Billingsley (30) - $14MM club option with a $3MM buyout
Joe Blanton (34) - $8MM club option with a $1MM buyout
Wei-Yin Chen (29) - $4.75MM club option with a $372K buyout
Kevin Correia (34)
Johnny Cueto (29) - $10MM club option with an $800K buyout
Jorge De La Rosa (34)
Ryan Dempster (38)
Yovani Gallardo (29) - $13MM club option with a $600K buyout
J.A. Happ (32) - $6.7MM club option
Dan Haren (34)
Luke Hochevar (31)
Hisashi Iwakuma (34) - $7MM club option with a $1MM buyout
Josh Johnson (31)
Kyle Kendrick (30)
Clayton Kershaw (27)
Jon Lester (31)
Colby Lewis (35)
Justin Masterson (30)
Brandon McCarthy (31)
Brandon Morrow (30) - $10MM club option with a $1MM buyout
Charlie Morton (31)
Jeff Niemann (32)
Ross Ohlendorf (32)
Felipe Paulino (31) - $4MM club option with a $250K buyout
Jake Peavy (34)
Wandy Rodriguez (36)
Max Scherzer (30)
James Shields (33)
Carlos Villanueva (31)
Ryan Vogelsong (37)
 
I'm assuming that Kershaw will get locked up before he hits FA.  After him you've got Gallardo, who has an option, and Scherzer as the most likely top guys available.  The odds are that Boston will need to sign someone, unless they're comfortable with Lackey, Doubront, Buchholz and two of the younger guys.  Is there anyone on this list people would feel comfortable about giving more money than Lester?
 

BeantownIdaho

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5/100 with an option gets it done...I think.  Maybe I am in the minority on this, but when you leave the game having earned 150 million verses 165 million, I don't really see a difference in your quality of life or the generations to come.  Of course I don't have 15 million in "flexibility." At that point it's all about your wisdom in handling and investing it.
 

ivanvamp

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Snodgrass'Muff said:
This is only a small part of your point but I thought it was worth pulling out. The starting pitching depth on the farm is as good as I've ever seen it, and may be the best in baseball right now, but I'm not sure that it's enough to be gun shy about extending Lester. After 2014 the team will have Peavy and Dempster off the payroll and both are old enough that bringing them back might not be a good use of resources. In 2015 Lackey's contract comes to an end. At that point they will have Clay Buchholz and Felix Doubront under control, whatever pans out on the farm and the free agent market.
 
Just to play off this, let's look at what the starting rotation costs in terms of contracted salaries.
 
2014
Lester - 13 m
Peavy - 14.5 m
Lackey - 15.3 m
Buchholz - 7.7 m
Dempster - 13.3 m
Doubront - 0.5 m
TOTAL - 64.3 m
 
Now I don't see them keeping all six guys for all of 2014, but regardless, that's what they're on the hook for right now.
 
2015
Peavy - 15 m (player option)
Lackey - 0.5 m (vesting option - yes!!)
Buchholz - 12 m
Doubront - 5 m (??? his first year of arbitration…no clue what he'll get)
TOTAL - 32.5 m
 
2016
Buchholz - 13 m (team option)
Doubront - 8 m (?? his second year of arbitration)
TOTAL - 21 m
 
Let's say they extend Lester at 6/120.  Here's what 2015 and 2016 could look like with Lester and some new guys filtered in.
 
2015
Lester - 20 m
Peavy - 15 m (player option)
Lackey - 0.5 m (vesting option - yes!!)
Buchholz - 12 m
Doubront - 5 m (??? his first year of arbitration…no clue what he'll get)
Workman - 0.5 m
TOTAL - 53 m - still $11 million less than 2014
 
2016
Lester - 20 m
Buchholz - 13 m (team option)
Doubront - 8 m (?? his second year of arbitration)
Workman - 0.5 m
Barnes - 0.5 m
Owens - 0.5 m
TOTAL - 42.5 m
 
Long story short, they can almost certainly afford to pay Lester and actually reduce the $$ allocated to starting pitching by bringing in the young guys piecemeal.  By 2016 I would expect Doubront, if he continues his developmental track, to be simply a very good #2 type pitcher, and if Clay is ever healthy, that's a really nice 1-2-3 at the top, with the three young guys filling in.  And there would also be enough financial room to add a veteran if they wanted to.
 
EDIT:  I recognize that my arbitration numbers may be off, but I'd have to be WAY off in order for the general premise to be erroneous.
 

jimbobim

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That should be an eye opening list. I think it's safe to say they could carry 2 much bigger contracts on this team. Ideally you'd make one a pitcher and one an everyday bat. Outside Scherzer and Kershaw none of those guys above are worth crossing the 100 mill threshold.  
 
Lester is not in Scherzer or Kershaw range in terms of consistency but his ceiling is there. Whatever they get paid will set a clearer expectation. 
 
Price is also supposedly open to an extension with the new team he gets traded to. I have no idea what the prospect price would be, but he's also probably comparable to what the market will dictate for Lester. Lester probably would get below his number both in AAV and Years because obviously Price is younger. 
 
Scherzer/ Kershaw/ Price (probably all going to far exceed the 100 mill threshold with teams buying them before they hit open market. 
 
Lester - Key question is years would 5 or 6 at 100-120 get it done ? 
 
Clearly different tiers but what the top tier gets will set a better expectation for what would be reasonable for them to offer Lester and what would be reasonable for him to accept. 
 

JimD

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I trust Farrell, Cherington and the staff on this.  These guys know Jon Lester and his mechanics.  They are also smart enough to figure out that, if they do decide to try and extend him, that the Pedey deal was an outlier and that they will likely have to pay closer to the market rate to retain Lester.  The fact that Cherington is already bringing this up tells me that they believe Lester is a good bet to be a productive pitcher well into his 30's.
 

threecy

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Likewise, I put a lot of faith in Farrell's assessment of Lester, as he seems to perhaps be Lester's best judge in all of baseball.  Clearly the change in approach in 2H helped turn around what was otherwise  looking like a disaster of a season for Lester.
The Red Sox should in theory have all of the leverage right now, since they don't really need to do anything for almost another year.  Probably the best time to offer him a Pedrioa-esque long term hometown deal.
I also wonder if he'd be amenable to a bonus frontended 3-4 year deal (including rolling 2014 into it).
Perhaps the Red Sox case to him with this theory would be that the next 3-4 years could be the deciding factor in terms of his legacy - if he can extend his 2H+post season success and have a few Cy Young caliber years, he would be back at the table at the end of his 32 or 33 year old season with potential Hall of Fame credentials in the making and thus be able to command Hall of Fame caliber pitcher's salary for another medium term deal.
 
 

smastroyin

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No matter what they try to sell him, I think Lester is smart enough to know that he is still a pitcher, and shit happens.  So if the Sox offered 3-4 years at a similar rate to others offering 5-6, I don't think he would be swayed by that argument.
 
I'm not sure where I fall on Lester.  I think he still has the stuff to be the pitcher he was from June 2008 - August 2011.  I believe that some continuity does have value for a team.  At the same time, I'm not sure locking him up until he is 35 is going to be the smartest thing for the Red Sox to do.  Lester has always been a guy who has in-season struggles for 3-4 starts.   So then you wonder if as he ages the bad starts will be more frequent and/or worse.  
 

The Boomer

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smastroyin said:
No matter what they try to sell him, I think Lester is smart enough to know that he is still a pitcher, and shit happens.  So if the Sox offered 3-4 years at a similar rate to others offering 5-6, I don't think he would be swayed by that argument.
 
I'm not sure where I fall on Lester.  I think he still has the stuff to be the pitcher he was from June 2008 - August 2011.  I believe that some continuity does have value for a team.  At the same time, I'm not sure locking him up until he is 35 is going to be the smartest thing for the Red Sox to do.  Lester has always been a guy who has in-season struggles for 3-4 starts.   So then you wonder if as he ages the bad starts will be more frequent and/or worse.  
 
Locking him up until age 35 isn't that much of an issue.  It's locking him up past that age that will be a problem.
 

Morgan's Magic Snowplow

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You see a lot of great pitchers showing attrition and substantial decline in the 33-35 age window.  I'd pay a premium in AAV to get him for his age 30-34 seasons and no longer.  If I'm Cherington, I offer 5/100 and am willing to negotiate that up to 5/110 or slightly higher, making the case to Lester that he locks in a huge payday, substantially ameliorates his risk, and has the opportunity to compete for more World Series titles with a bunch of teammates that he loves.  If the Lester camp makes it six years or bust, I probably walk away and reevaluate next offseason after seeing the progression of the minor league kids.
 

bankshot1

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For the sake of argument lets assume Jon Lester pitches like a 1-2 for the next 4+ years, (if you're not willing to make that assumption, you shouldn't be interested in signing him to an extension in the first place) would you balk, at a 5/100+ million extension, because of the risk he falls to a 4-5 by the 5th year?
 

MakMan44

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Morgan's Magic Snowplow said:
You see a lot of great pitchers showing attrition and substantial decline in the 33-35 age window.  I'd pay a premium in AAV to get him for his age 30-34 seasons and no longer.  If I'm Cherington, I offer 5/100 and am willing to negotiate that up to 5/110 or slightly higher, making the case to Lester that he locks in a huge payday, substantially ameliorates his risk, and has the opportunity to compete for more World Series titles with a bunch of teammates that he loves.  If the Lester camp makes it six years or bust, I probably walk away and reevaluate next offseason after seeing the progression of the minor league kids.
I agree with this and I think he FO will too. They've placed a premium on AAV to keep the deals shorter. It's worked out so far, we'll see if Lester is willing to sign an extension like that.
 

Bigpupp

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ivanvamp said:
2015
Peavy - 15 m (player option)
Lackey - 0.5 m (vesting option - yes!!)
Buchholz - 12 m
Doubront - 5 m (??? his first year of arbitrationno clue what he'll get)
TOTAL - 32.5 m
Peavy would have to pitch about 256 innings next year for his player option to vest. I don't see that happening.
 

koufax37

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I spent a lot of the season talking about how Lester was a #2/#3 and really lacked either ace command or ace stuff, and certainly lacked the super-ace combination of both.  He then proceeded to step up and shut me up during the playoffs, which I was very excited about since I root for him, but just don't evaluate him highly.
 
He clearly took a step forward moving from Bobby the Fifth back to Farrell, and there is hope that he could continue this trend, and take the upswing in the craft of pitching that many left handed starters do in their early 30s.  I have never viewed him as a real student or command pitcher and have projected him to be mediocre as he ages and loses some of his stuff.  Increasing his command and craft is the key to his future value, and projecting the likely degree of this is the key to understanding what contract might make sense.
 
I don't view him as an injury risk overall, and even on the low end of his projections he is a solid reliable #3 who eats innings and has flashes of brilliance, and doesn't wilt on the big stage.  That in itself has tremendous value, and is worthy of a big contract.  But when that contract starts being into the true dominant ace levels of dollars/years, you need to realize that his comps are not Verlander/Felix/Kershaw/Hamels, and if you are putting him in that range you are setting yourself up for an overpay that hurts financial flexibility down the road.
 
So when 5/90 is thrown out, I am probably on board, but when we talk about 6+ years and $20M+ AAV I think he enters the overpay category.  We might want to consider a slight overpay for a solid established player loyal to our team, and we might in calculating the value of a #2/#3 who is a lock for 200IP to be more than we initially thought.
 
But just don't pay him like an ace and expect him to live up to it.  Evaluate his last 1000 innings and project his next 1000 innings, and don't enter into a bad contract over his last 50 innings and the bling of his second WS ring.
 

Sprowl

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Lester put an extra 2 mph on his fastball and remastered his cutter during the second half of the season, and sustained them both throughout the playoffs. It was a great performance, and bodes well for his longevity. With a starting rotation of Lester-Buchholz-Lackey, it's hard to say that any of them is an ace, but it is an imposing first three for a playoff series.
 

Toe Nash

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Sprowl said:
Lester put an extra 2 mph on his fastball and remastered his cutter during the second half of the season, and sustained them both throughout the playoffs. It was a great performance, and bodes well for his longevity. With a starting rotation of Lester-Buchholz-Lackey, it's hard to say that any of them is an ace, but it is an imposing first three for a playoff series.
You know more about this than me, but why does this bode well for his longevity? One could argue that he needs the extra 2 mph to succeed and that may not be there consistently for him going forward as it hasn't been over the past couple years.
 

jimbobim

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Lester will easily clear 100 million on the open market. He will get paid like an ace even if his past inconsistency raises risk. If the FO balks at the gap between ace payment and likelihood of ace performance from Lester than they should either be looking around to  get a Sherzer or Price type to capitalize on his last year or look to see what he could get for him in a trade which they have shown no inclination of doing whatsoever (for good reason).  
 
M

MentalDisabldLst

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Here is a list of potential free agents next year.
 
<snip>
 
I'm assuming that Kershaw will get locked up before he hits FA.  After him you've got Gallardo, who has an option, and Scherzer as the most likely top guys available.  The odds are that Boston will need to sign someone, unless they're comfortable with Lackey, Doubront, Buchholz and two of the younger guys.  Is there anyone on this list people would feel comfortable about giving more money than Lester?
 
I would be just fine with James Shields (despite his age, his odometer is lower), but I take your larger point.
 

Sprowl

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Toe Nash said:
You know more about this than me, but why does this bode well for his longevity? One could argue that he needs the extra 2 mph to succeed and that may not be there consistently for him going forward as it hasn't been over the past couple years.
 
Before last year, I was not sure he had it in him to throw 94 anymore -- he seemed to be bulking up and losing velocity on the fastball and confidence in the cutter. Whether it was a different conditioning regime or Farrell and Nieves helping him with his mechanics, he recovered the tools of a power pitcher. With his cutter improving as a weapon against LHB (it has always been deadly against RHB when his arm angle was right), the stretches of dominance should be expected to recur.
 

nvalvo

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As I look into these rate stats, his dreary 2012 looks more and more like a HR/FB spike and a LOB rate collapse. Now, the HR/FB might have been due to declining stuff/poor location, but the LOB rate? Doubtful. (And a high BABIP, too.)
 
LOB% (2008-13): 77.4%, 76.9%, 74.5%, 78.1%, 67.6%, 73.7%.
 
2012 stands out. 
 
HR/FB: 7.0%, 10.6%, 8.9%, 11.4%, 13.9%, 8.3%. 
 
This has bounced around a fair amount (as is typical), but still, 2012 was the peak. 
 
I see a guy who's started 32 games and thrown 200+ innings on average since 2008. That's tremendously valuable even if the quality declines somewhat. Especially as we introduce the young SP prospects, having a couple pitchers who can reliably throw innings would smooth things over. 
 
As long as his shoulder checks out okay, I'd say he's a good bet to earn 5/$100. 
 

glennhoffmania

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MentalDisabldLst said:
 
I would be just fine with James Shields (despite his age, his odometer is lower), but I take your larger point.
 
I would too, but for fewer years.  I would have zero interest in giving Shields the 5 or 6 years people are talking about here for Lester, but 3 or 4 years at a higher AAV wouldn't be the worst thing in the world.
 

koufax37

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In 2012, he really pitched poorly.  Not luck and results and other stuff, but simply pitching worse both in stuff and command.  His rebound this year was very encouraging, especially performing well down the stretch, and the improved velocity Sprowl mentions.  But what matters most for him to live up to an ace-like contract is if over the next five years minimize the inevitable decline in his stuff, and make up for it with improved command and knowledge.  Prior to this season I would definitely have said that seemed unlikely, but he has shown a lot to be hopeful about over the last couple months.
 
I am still wary about reading more into a 50-100 IP sample over a 600-800 inning trend, but we know at the micro level that the dysfunctional finish to 2011 rolling into the mayhem of 2012 into the return of Farrell in 2013 plays out like a Hollywood trilogy with a happy ending.  A player like Lester could have been affected significantly, since players are not the cold robots we sometimes want to portray them as in statistical analysis.
 
I don't think it is likely we end up with three guys in our rotation better than he is over the next five years, meaning his departure would be a significant blow and extending him need to be a priority.  But as we saw with Ellsbury and Cano, when the market overvalues your player, sometimes you have to offer your best, and deal with the loss due to another team's overpay.
 
I'm hopeful that that will not happen, and that there is more Pedroia than Ellsbury in him at the negotiating table, but paying him ace dollars would be a big risk to our financial flexibility that could make his contract weigh us down over time.
 

rembrat

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The only guy signed passed 2015 is Dustin Pedroia. Paying Lester $15-20MM a year will not cripple the franchise.
 

Al Zarilla

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koufax37 said:
In 2012, he really pitched poorly.  Not luck and results and other stuff, but simply pitching worse both in stuff and command.  His rebound this year was very encouraging, especially performing well down the stretch, and the improved velocity Sprowl mentions.  But what matters most for him to live up to an ace-like contract is if over the next five years minimize the inevitable decline in his stuff, and make up for it with improved command and knowledge.  Prior to this season I would definitely have said that seemed unlikely, but he has shown a lot to be hopeful about over the last couple months.
 
I am still wary about reading more into a 50-100 IP sample over a 600-800 inning trend, but we know at the micro level that the dysfunctional finish to 2011 rolling into the mayhem of 2012 into the return of Farrell in 2013 plays out like a Hollywood trilogy with a happy ending.  A player like Lester could have been affected significantly, since players are not the cold robots we sometimes want to portray them as in statistical analysis.
 
I don't think it is likely we end up with three guys in our rotation better than he is over the next five years, meaning his departure would be a significant blow and extending him need to be a priority.  But as we saw with Ellsbury and Cano, when the market overvalues your player, sometimes you have to offer your best, and deal with the loss due to another team's overpay.
 
I'm hopeful that that will not happen, and that there is more Pedroia than Ellsbury in him at the negotiating table, but paying him ace dollars would be a big risk to our financial flexibility that could make his contract weigh us down over time.
He had mechanical problems for a lot of 2012 that the inmates running the asylum that year apparently couldn't see, even though the old ball manager here saw them on TV. Farrell and Nieves said before 2013 they saw some things in him (essentially the same things), and they fixed him, at least for most of the year. Post season was magical for Lester, of course. Hopefully, Farrell and Nieves and Lester himself don't allow him to fall back on the bad form.
 

HriniakPosterChild

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If the Sox do not extend him, there will surely be a QO. And Lester will surely decline it, if we get to that point. So that will be a bit of a poison pill for any team that would like to sign him. 
 
Of course, if a team is in "load up on free agents" mode, they will spend hundreds of millions of dollars and buy them in bulk, minimizing the effect of any single QO. (e.g. NYY 2008-09).
 
If NYY actually wins the Fiscal Responsibility Series this offseason, the Sox would have added urgency to nail down a deal with Lester while the Yankees front office has their parade through the Canyon of Heroes. (That is, before Opening Day 2014.) If NYY does not get below the tax threshold this year, I think there is somewhat less risk of NYY concluding a deal with Lester after this season ends.
 

keninten

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If the Sox don`t get him signed for 5/100 or 6/120, he will cost a lot more after the season. I think contracts after this season are going to skyrocket.
 

TomRicardo

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HriniakPosterChild said:
If the Sox do not extend him, there will surely be a QO. And Lester will surely decline it, if we get to that point. So that will be a bit of a poison pill for any team that would like to sign him. 
 
Of course, if a team is in "load up on free agents" mode, they will spend hundreds of millions of dollars and buy them in bulk, minimizing the effect of any single QO. (e.g. NYY 2008-09).
 
If NYY actually wins the Fiscal Responsibility Series this offseason, the Sox would have added urgency to nail down a deal with Lester while the Yankees front office has their parade through the Canyon of Heroes. (That is, before Opening Day 2014.) If NYY does not get below the tax threshold this year, I think there is somewhat less risk of NYY
concluding a deal with Lester after this season ends.
 
No team that is going to sign Lester is going to pause over a QO.  QO's affect players like Stephew Drew which are borderline QOs.
 

Drek717

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I've always thought Lester was a pretty good comp to Andy Pettitte.  While Pettitte has since admitted to using steroids to help him bounce back from injury I don't think you can dismiss his exceptional longevity on that basis.  Lester is a workhorse with a strong repertoire and a lot of pitcher IQ.  Not only does he seem like the kind of guy who would age gracefully as-is, he also seems like the kind of pitcher who if necessary and given the right supporting staff around him could retool his game in his 30's to maintain effectiveness.
 
Personally I'd like to see the Sox offer 6/$111 added on to his current deal.  That's 18.5M per season and would carry him through to age 36.  I don't see Lester as the kind of guy who is completely toast by 36.  Also, given what the market has paid SPs the last two off-seasons I'd argue that by 2020 an 18.5M salary will be pretty mainstream for middle of the market free agent starters.
 
To me Lester is an example where the team should pay more in years to reduce the dollars per year.  The FA market for starters will out-pace any non-insane deal they give him.  If it takes added security to lock him up for less than $20M a season I'd go for it as I'd much rather give 36 year old Jon Lester that $18.5M than the 2020 comparison to Ryan Dempster.
 

Snodgrass'Muff

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Also, given what the market has paid SPs the last two off-seasons I'd argue that by 2020 an 18.5M salary will be pretty mainstream for middle of the market free agent starters.


The market is still adjusting to the new financial landscape birthed by the TV deal MLB recently signed. The rate at which AAV has been rising will level off a bit at some point, so I wouldn't be so quick to assume they will continue to rise at this rate through the 2020 season.
 

Otis Foster

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For the NYY, snaring Lester (if there's no extension) would be a double play - they sign a very capable pitcher while at the same time taking a prominent LHP away from their divisional rivals. Right now, it doesn't appear that they'll develop any significant pitching talent on their own over the next several seasons, so FAs will continue to be a priority for the time being, and as matters now stand, Lester will be at the top of the list .
 
This continues to be a paradox for the Skanks. While they profess to devoting necessary resources to rebuild their farm, they're under continued pressure - from the NY press and from the Steinbrenner boys - to win immediately with high profile FAs, meaning loss of draft choices. We all remember hat the RS were originally viewing 2013 as a 'bridge (meaning rebuilding) year' even though things turned out quite differently. NYY seem incapable of walking this talk. 
 
Edit: clarified that the Skanks likely won't develop their own pitching talent over the short term.
 

Morgan's Magic Snowplow

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Drek717 said:
I've always thought Lester was a pretty good comp to Andy Pettitte.  While Pettitte has since admitted to using steroids to help him bounce back from injury I don't think you can dismiss his exceptional longevity on that basis.  Lester is a workhorse with a strong repertoire and a lot of pitcher IQ.  Not only does he seem like the kind of guy who would age gracefully as-is, he also seems like the kind of pitcher who if necessary and given the right supporting staff around him could retool his game in his 30's to maintain effectiveness.
 
I see some resemblance but I wouldn't overstate it.  Pettitte was never much of a power pitcher or a strikeout guy in this 20s and early 30s and he had significantly better command and control than Lester, with the exception of a couple lean years in the late 1990s.  He actually struck out more guys in his 30s than he did in his 20s.  Lester is likely to have a much more standard trajectory - in fact, we're already seeing it - of a power/strikeout pitcher in his 20s who sees the quality of his stuff decline in his 30s and must learn to get by in other ways.  Maybe he does, maybe he doesn't, but I don't think Andy Pettitte's career means all that much in projecting Lester's.
 

JimD

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Otis Foster said:
For the NYY, snaring Lester (if there's no extension) would be a double play - they sign a very capable pitcher while at the same time taking a prominent LHP away from their divisional rivals. Right now, it doesn't appear that they'll develop any significant pitching talent on their own over the next several seasons, so FAs will continue to be a priority for the time being, and as matters now stand, Lester will be at the top of the list .
 
 
Only if Scott Boras is abducted by aliens.  There is no way he lets Max Scherzer sign an extension with Detroit or any team he is traded to (unless he is traded to the Yankees).
 
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