Extending Lester

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mauf

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If you remove the 2012 fiasco, Lester's numbers look a whole letter better in those comps. Not sure why folks are unwilling to consider 2012 an outlier given the circumstances.


I think Hoplite hits the nail on the head -- of course Lester's 2012 ERA is an outlier (hideous strand rate, below average BABIP luck), but his peripherals have been remarkably steady the past two years. That's the guy he is now -- not the elite guy we had in 2009, 2010, and part of 2011.

I'm still in favor of an extension, provided the FO feels good about his outlook health-wise (their private information likely provides more insight than his track record, which is obviously excellent), and provided Lester accepts some kind of discount off what a durable 30yo SP with a high 3s ERA commands on the open market.
 

Sampo Gida

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The thing about Lesters 2011-2013 is he was really 2 pitchers, Jekyll and Hyde.  He was great the first 5 months of 2011 and fell of a cliff in September.  In 2012 he was pretty bad for 4 months and finished strong the last 2 months.  In 2013, he again was not very good for 4 months, and outstanding the last 2 months into the post season.
 
The Red Sox will have to have a pretty good handle on the cause of the inconsistency in this period before committing to any extension approaching 100 million.  If it is something benign (mechanics, approach)  they go for it. If something more malignant, mental or physical, they think harder about it.  
 

snowmanny

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In 2013 he had a 10 game stretch where he had a 6.49 ERA.  In his other 28 starts he had a 2.48 ERA.  
 

Toe Nash

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Sampo Gida said:
The thing about Lesters 2011-2013 is he was really 2 pitchers, Jekyll and Hyde.  He was great the first 5 months of 2011 and fell of a cliff in September.  In 2012 he was pretty bad for 4 months and finished strong the last 2 months.  In 2013, he again was not very good for 4 months, and outstanding the last 2 months into the post season.
I think this kind of thing happens with most pitchers who are good but not elite (for argument's sake we'll call elite top ten). Pitching is hard and there are stretches where they're not 100% physically, mechanically or mentally where they lose it and it takes time to find "it" again. Or sometimes you just have bad luck, or your manager who you hate leaves you out there to give up 11 runs when you're obviously not having a good day and ruins your ERA. Fortunately we have DIPS to help us find some of the truth here.
 
The very best are able to figure out ways to get through these stretches with good results, or they just have fewer such stretches to begin with. That may have described Lester from 2008-2010, but probably not now. But that's OK since Lester's very best stretches seem to have come at the most important times and with the current manager, and because he's willing to take a little less money to be in that situation. If he can keep up his 2011-13 (underlying) performance at a discount then I'm happy, and I'll hope he continues the trend of being at his best in the postseason. But as we saw with Josh Beckett, just a seemingly small oblique tweak can turn a guy from a postseason ace to someone who loses the ALCS for you...
 

donutogre

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snowmanny said:
In 2013 he had a 10 game stretch where he had a 6.49 ERA.  In his other 28 starts he had a 2.48 ERA.  
 
Yeah, I'm not really sure where the "he sucked for 4 months in 2013" thing is coming from. He had a pretty bad, discouraging stretch, but it was bookended by a solid start to the year and an excellent finish. The best pitchers around don't have these bad stretches, so I don't disagree with people saying he isn't quite at ace level... but he's durable, has had great success in Boston and wants to stay here, and seems like he's up for a team-friendly deal. I'd be fine with a 5/100 deal.
 

Hoplite

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Anything approaching $100 million would make me nervous. As great as he was in the second half of last year, he also had a 3.9% HR/FB rate which is completely unsustainable. Last year, as a whole, he was roughly league average according to xFIP- (98) and SIERA (3.97) an he was only slightly better in those metrics the year before. If we sign him to a five year extension, we'd be paying him through his age 34 season at least (if the extension began this year). $20 million a year seems like a lot for a 30+ year old pitcher who's been slightly above league average the last two seasons, postseason heroics or not.
 

Sampo Gida

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donutogre said:
 
Yeah, I'm not really sure where the "he sucked for 4 months in 2013" thing is coming from. He had a pretty bad, discouraging stretch, but it was bookended by a solid start to the year and an excellent finish. The best pitchers around don't have these bad stretches, so I don't disagree with people saying he isn't quite at ace level... but he's durable, has had great success in Boston and wants to stay here, and seems like he's up for a team-friendly deal. I'd be fine with a 5/100 deal.
 
Well, that solid start consisted of his first 4 starts and he dropped off pretty quick after that even if those first 4 starts kept his numbers looking respectable through May..
 

Apisith

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Sampo Gida said:
 
Well, that solid start consisted of his first 4 starts and he dropped off pretty quick after that even if those first 4 starts kept his numbers looking respectable through May..
 
That's not true. His first 9 starts he had an ERA of 2.72. The last two of those starts were a complete game shut out against TOR and a solid 7 innings against TAM where he only gave up 2 runs.
 
He then had a terrible stretch of 8 starts where his ERA was 6.99. That was from middle of May until the end of June, far from sucking for '4 months'.

From July until the end of the season, he pitched 106 innings and had an ERA of 2.89. That's three straight months of elite pitching. Then he had 5 more starts in the postseason with an ERA of 1.56. The guy had an ace-like year apart from one and a half months of sucking. How likely is it that he goes through that terrible stretch again?
 
If Farrell believes that the period of sucking was an anomaly - say a mechanical problem which is unlikely to resurface - then I'd be okay with something like 6/$110m. I could see the FO offering him 5/$90m, with a team option and buyout for the 6th year, guaranteeing him a further $5m. It'd be potentially 6/$110m, but 5/$95m in guaranteed terms. I don't think he's worth $20m/year. He's much older and worse than the other pitchers who are paid that were when they signed their deals, and he's also a year away from FA. If both parties are reasonable, the AAV should be below $20m.
 

LondonSox

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I rely think you guys are missing the developments in the market, and how much money is coming in for teams.
Contracts are exploding, I can think of only half a dozen that don't seem Hugh this offseason.
Pitchers who are good aren't hitting free agency without at least one major question. They just get locked up most of the time.

It's nice the sox get discounts. It's nice that the front office has a farm that allows them to focus on the right players and let aging expensive ones leave but let's not get carried away. Wages are rising, contract are getting bigger. What ever he signs is likely to look cheap in a year or two anyway imo.
Get a below market deal for a good pitcher who wants to be here. Move on.
 

joe dokes

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Apisith said:
 
He then had a terrible stretch of 8 starts where his ERA was 6.99. That was from middle of May until the end of June, far from sucking for '4 months'.
From July until the end of the season, he pitched 106 innings and had an ERA of 2.89. That's three straight months of elite pitching. Then he had 5 more starts in the postseason with an ERA of 1.56. The guy had an ace-like year apart from one and a half months of sucking. How likely is it that he goes through that terrible stretch again?
 
If Farrell believes that the period of sucking was an anomaly - say a mechanical problem which is unlikely to resurface - then I'd be okay with something like 6/$110m. I could see the FO offering him 5/$90m, with a team option and buyout for the 6th year, guaranteeing him a further $5m. It'd be potentially 6/$110m, but 5/$95m in guaranteed terms. I don't think he's worth $20m/year. He's much older and worse than the other pitchers who are paid that were when they signed their deals, and he's also a year away from FA. If both parties are reasonable, the AAV should be below $20m.
 
 
It's quite likely that he has a stretch like that. Just about *every* pitcher *every* year that ends up with what we could call a *good* year has a strecth where they aren't as good as they have been in other stretches. He's not Pedro 99-01; or mid-80s Clemens; or present day Kershaw.  Even if you can *guaranteee* that he'd have a stretch like that *every* year, he'd still be worth it.
 
"When they signed their deals" is a pretty big point. You cant compare what players get paid right now to what they got 1, 2 5, or 50 years ago. He's older than Sandy koufax was when *he* signed his last deal, he's worse than Koufax and Koufax made a lot less. Every year is a different market.
 

jimbobim

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As someone who often is frustrated when the Hyde version of Lester  sometimes shows up I have to say he's still worth 5 for 100 starting this year. That takes him to his age 35 season which is around where they felt comfortable with Lackey age wise. 
 
Also this kind of reminds me of the Ravens and the Flacco signing even though the two sports are completely different economically. Two inconsistent players who the teams were leery about reinvesting big money in with years left on their contracts who then had to go out for a season and prove themselves. Flacco got a no discount franchise qb type contract after a freakish Super Bowl run while Lester was basically the best you could have hoped for in carrying the team to a World Series. 
 
I dont think the Red Sox will give him much over 100 million, but I do think they'd rather go high on the AAV then long on the years. For example is 4 for 92 more appealing compared to 5 for 100 ? 
 

FanSinceBoggs

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If Lester is worth 5 years 100 million (I'm not convinced Lester is worth 20 million per year--a guy with an ERA+ of 109 is worth 20 million per year?) then a discount would be something like 5 years at 90 million, I suppose.  I'm generally skeptical when players say they will take a discount.  Usually that means they will overvalue their worth, and, in turn, estimate the "discount" at market value.
 
If Bailey has another strong season in 2014, I would rather give him the 5 year contract and lock him up from ages 29 to 33 and get the draft pick for Lester.  True, Lester and Bailey's ERA+ were nearly identical in 2013 (whereas Bailey had a major edge in 2012), but Bailey's K rate was better than Lester's and I'm buying two seasons of youth: Bailey at 32 and 33 versus Lester at 34 and 35.
 

DGreenwood

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That makes more sense now.  The "lock him up" phrase made me think he was talking about someone already with the team.
 

snowmanny

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But he said "get the draft pick for Lester."  Signing Bailey means losing a (higher) draft pick.  So it was confusing.
 
I'm not sure the age difference is worth the trade-off in handedness and health history.  I'd bet on Lester from 2015-19 over Bailey.
 

Hoplite

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snowmanny said:
But he said "get the draft pick for Lester."  Signing Bailey means losing a (higher) draft pick.  So it was confusing.
 
I'm not sure the age difference is worth the trade-off in handedness and health history.  I'd bet on Lester from 2015-19 over Bailey.
 
How is Lester's handedness a plus? 2/3rds of hitters are righthanded, and Fenway Park is more difficult for lefthanded pitchers to pitch in.
 

snowmanny

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It's a mystery why the Red Sox keep drafting left-handed  pitchers like Ball and Owens since they are going to face those disadvantages.
 
I do believe that left-handers have a better shot at longevity, but I'm open to other evidence.
I do think three DL stints for shoulder injuries << six straight years of 30+ starts.
 

TFisNEXT

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Hoplite said:
How is Lester's handedness a plus? 2/3rds of hitters are righthanded, and Fenway Park is more difficult for lefthanded pitchers to pitch in.
If they have the AL East competition in mind, then it makes more sense. Of the 4 opponents' parks in the East, 3 of them are much more HR-friendly to LHB than RHB. Only Toronto is not. Used a 3 year split from statcorner to reduce the noise.

Obviously the East isn't the only competition, but certainly the unbalanced schedule makes it more important. As for Fenway, it's a unique park in that while HRs are suppressed for LHB naturally, the park is more faovrable for non-HR extra base hits for LHP than RHP. Lefties get a lot more doubles and triples so it makes up a chunk of the gap. Something that is not true of the other visiting parks in the East.

In short, LHBs enjoy some good hitting conditions in the AL East which would make having a lefty starter more attractive despite the Fenway Factor on LHB HRs.


edit: grammar
 

Red(s)HawksFan

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Hoplite said:
 
How is Lester's handedness a plus? 2/3rds of hitters are righthanded, and Fenway Park is more difficult for lefthanded pitchers to pitch in.
 
In his career, he's made 103 starts at Fenway and 117 starts away from Fenway (regular season only).  ERA at Fenway = 3.78, ERA away from Fenway = 3.74.  So if it is more difficult for a typical left handed pitcher to succeed at Fenway, that would make a lefty who CAN succeed at Fenway more valuable, would it not?
 
The team plays half its games outside of Fenway Park, including in some LHH-friendly parks and against some lineups with strong LHH.  I'd say his handedness becomes a plus in those situations.
 

Hoplite

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No doubt there are certain situations where it helps to be lefthanded, and Lester deserves Kudos for being a lefthanded pitcher who can pitch well in Fenway. But there are more situations overall where it helps to be righthanded, so I'd be more concerned with the overall performance. 
 

Al Zarilla

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Hoplite said:
No doubt there are certain situations where it helps to be lefthanded, and Lester deserves Kudos for being a lefthanded pitcher who can pitch well in Fenway. But there are more situations overall where it helps to be righthanded, so I'd be more concerned with the overall performance. 
So, you'd have 100% right handed starting pitchers? Hurst in the 80s and Lester now show that having the ability to go RLR, or, simpler, having a lefty going into NY that can also pitch well in Fenway is a very good thing. Another thing, the Sox came close to sending a lot of young talent after another lefty, Johan Santana (one being Lester). Thankfully, that didn't happen. LH starting pitchers, if a team can get them, are important to have for any team, IMO. 
 

Red(s)HawksFan

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All batters vs RHP in 2013: .254/.318/.398
All batters vs LHP in 2013: .252/.317/.393
 
RHP vs RHH in 2013: .249/.307/.384
LHP vs LHH in 2013: .235/.295/.350
 
RHP vs LHH in 2013: .259/.329/.412
LHP vs RHH in 2013: .260/.326/.412
 
Seems to me that it's most inconsequential whether the pitcher is right or left handed.  The batting numbers against are practically identical.  But left handed pitchers suppressed left handed hitters to a greater degree than right handed pitchers suppressed right handed hitters.
 
Given that LHP are a rarer commodity than RHP (roughly two righties for every lefty), I think that gives them a bit more value overall.
 

Homar

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I confess that I'm having a hard time overcoming the emotional hurdle of $20M annually.  Since the first A-Rod contract with Texas, $20M+ contracts have been the province of the truly exceptional, the once in a generation player.  Now, however, with the huge infusions of new TV money, we're going to see more and more high quality players shoot past this threshold.  The teams have the money, they're competitive, and they are willing to pay for the upgrade in wins.  Increasingly it appears rational to pay for a larger pool of players what used to be thought of as exceptional money.  When I'm in my rational mind, I have no problem with Jon Lester being worth $20-22M AAV.  I think the performance justifies it.  I can still hear the little voices in my head that say Lester?  Lester?  $22M for Lester?  But they've not adjusted to the new market.
 
Is anyone hearing discussion about raising the $189M luxury tax line?  As more teams get silly TV money, it won't belong before the teams bumping up against that limit are in double digits, and it'll be harder to restrain themselves, especially as they try to compete.  I know the small market teams would object; but the players are not going to want to hang onto a system which has rich clubs paying in taxes to the poor ones salaries that could be going to players.  Will this be a part of the next CBA negotiations?
 

Al Zarilla

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Red(s)HawksFan said:
All batters vs RHP in 2013: .254/.318/.398
All batters vs LHP in 2013: .252/.317/.393
 
RHP vs RHH in 2013: .249/.307/.384
LHP vs LHH in 2013: .235/.295/.350
 
RHP vs LHH in 2013: .259/.329/.412
LHP vs RHH in 2013: .260/.326/.412
 
Seems to me that it's most inconsequential whether the pitcher is right or left handed.  The batting numbers against are practically identical.  But left handed pitchers suppressed left handed hitters to a greater degree than right handed pitchers suppressed right handed hitters.
 
Given that LHP are a rarer commodity than RHP (roughly two righties for every lefty), I think that gives them a bit more value overall.
Thanks for digging up those numbers. My post was mostly just a statement that lefties were somewhere between a nice to have and a must have for any baseball team. The numbers back it up.
 

Hoplite

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Al Zarilla said:
So, you'd have 100% right handed starting pitchers? Hurst in the 80s and Lester now show that having the ability to go RLR, or, simpler, having a lefty going into NY that can also pitch well in Fenway is a very good thing. Another thing, the Sox came close to sending a lot of young talent after another lefty, Johan Santana (one being Lester). Thankfully, that didn't happen. LH starting pitchers, if a team can get them, are important to have for any team, IMO. 
 
No, I don't believe I suggested that. I just don't think I'd give the lefthanded thing all that much weight. It's a nice bonus to have, but I don't think it should be a deciding factor in whether we extend Lester or attempt to sign a better overall pitcher like Homer Bailey.
 

Red(s)HawksFan

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Hoplite said:
 
No, I don't believe I suggested that. I just don't think I'd give the lefthanded thing all that much weight. It's a nice bonus to have, but I don't think it should be a deciding factor in whether we extend Lester or attempt to sign a better overall pitcher like Homer Bailey.
 
How exactly is Homer Bailey the "better overall pitcher"?  Other than being two years younger, I'm not seeing him as a decidedly better option regardless of handedness.
 

Al Zarilla

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Hoplite said:
 
No, I don't believe I suggested that. I just don't think I'd give the lefthanded thing all that much weight. It's a nice bonus to have, but I don't think it should be a deciding factor in whether we extend Lester or attempt to sign a better overall pitcher like Homer Bailey.
"But there are more situations overall where it helps to be righthanded, so I'd be more concerned with the overall performance."
 
That's the sentence I was keying on that made it sound like you're always better off with RH pitchers. As for Homer Bailey, he has pitched only two full seasons in the majors. I couldn't begin to compare him to a horse like Lester. 
 

Hoplite

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Red(s)HawksFan said:
 
How exactly is Homer Bailey the "better overall pitcher"?  Other than being two years younger, I'm not seeing him as a decidedly better option regardless of handedness.
 
Last season:
Bailey: 209 IP, 92 ERA-, 87 FIP-, 89 xFIP-, 3.30 SIERA
Lester: 213.1 IP, 90 ERA-, 87 FIP-, 98 xFIP-, 3.97 SIERA
 
Last two seasons:
Bailey: 417 IP, 92 ERA-, 93 FIP-, 95 xFIP-, 3.62 SIERA
Lester: 418 IP, 102 ERA-, 91 FIP-, 95 xFIP-, 3.96 SIERA
 
You could make a case that Lester's been a good pitcher for longer, but I explained earlier in the thread why I didn't consider Lester's numbers from more than three years ago to be representitive of the pitcher that he is now. And I'd rather have the younger pitcher who's trending towards pitching better than the older pitcher who is trending towards performing worse.
 

Minneapolis Millers

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Hoplite said:
 
No, I don't believe I suggested that. I just don't think I'd give the lefthanded thing all that much weight. It's a nice bonus to have, but I don't think it should be a deciding factor in whether we extend Lester or attempt to sign a better overall pitcher like Homer Bailey.
I find this sort of argument frustrating.  Ok, let's assume Bailey is slightly better than Lester. He's younger. Great.  Where has he indicated an intense desire to play for Boston, and to do so at a discount?
 
If good SPs were readily available every year, then I'd appreciate your point more.  But they're not.  We'll have Dempser, Peavy and Lackey money to spend next year.  Will there be a FA starter we like more than Lester?  And will he be available be for what we might sign Lester for now??
 
No one's advocating throwing stupid money at Lester.  But 5/100 is a manageable deal for this team, and could be the best available such investment over the next year.  If they can get him for 10m less, great.  
 

Hoplite

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Minneapolis Millers said:
I find this sort of argument frustrating.  Ok, let's assume Bailey is slightly better than Lester. He's younger. Great.  Where has he indicated an intense desire to play for Boston, and to do so at a discount?
 
If good SPs were readily available every year, then I'd appreciate your point more.  But they're not.  We'll have Dempser, Peavy and Lackey money to spend next year.  Will there be a FA starter we like more than Lester?  And will he be available be for what we might sign Lester for now??
 
No one's advocating throwing stupid money at Lester.  But 5/100 is a manageable deal for this team, and could be the best available such investment over the next year.  If they can get him for 10m less, great.  
 
I didn't say that I didn't want to extend Lester, I said that I didn't want to extend Lester right now on a contract approaching $100 million. He will be in his age 30 season next year and whether or not people believe the second half 2013 Lester or the September 2011-June 2013 Lester is more representative of the actual pitcher that he is, I don't think there's any denying that his production has declined over the last 2-3 years. And as much as I'd love to think that Lester's talking extension now because he loves the Red Sox, he probably also knows that his value is higher right now than it has been in years. The point isn't so much that I'm in love with Homer Bailey. It's that if we can't get Lester to sign an extension on our terms, that we should feel comfortable letting next year play out, seeing what kind of a pitcher he looks like, seeing how our prospects develop and if necessary offering him a qualifying offer and allowing him to become a free agent. If he then ultimately walks, I don't think it would be the end of the world. I threw Homer Bailey's name out there because I thought he was one of the more likely targets. But it's also possible that Max Scherzer becomes a free agent. Justin Masterson may also become a free agent and I don't consider Lester significantly better than him.
 

KillerBs

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I hope they sign Lester, and would not be especially troubled by something in the 5/100 range for his 31-35 years, but the track record on lefty starters sustaining success over this length of time certainly gives one pause.
 
I counted a total of 36 lefty starters in the last 50 years who had at least 4 "good years" before turning 30 years old.I defined a "good year" as 25 starts with an ERA+ of 105 or greater, ie more or less arbitrarily, but at a level where you would pretty surely not want to pay 20 million for anything less.Lester has had 5 such years already at the age of 29. This in itself is very rare accomplishment.
 
Of these 36 consistently good young left handed starters, no more than 10 sustained any success into their mid 30s: Pettitte, Tanana, Kaat, Buehrle, Guidry, Carlton, Glavine, John and very charitably Blue and Valenzuela.   5 few more (Osteen, Danny Jackson, Langston, Floyd Bannister, VIola) had their last "good season" at 32-33. The jury is still out on Sabathia, Kershaw, Hamels and Price. That leaves 17, almost 1/2, who were of little or no value on and after the age of 30. Here is a list of these elite young lefties and their age in their last "good year."
 
Zito 31
Chris Short 29
McNally  30
Neagle 31
Doug Rau 29
Fritz Peterson 29
Swindell 27
Santana 31
Candalaria 30
Matlack 30
Holtzman 29
Mulder 27
Hampton 30
Grimsley 28
MacDowell 28
Sid Fernandez 29
Alvarez 29
 
On the other hand, this is Jon F'in Lester, we are talking about...
 

Hairps

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Speier, as usual, does a great job looking at a potential Lester extension:
 
http://www.weei.com/sports/boston/baseball/red-sox/alex-speier/2014/01/27/life-after-30-what-will-jon-lester-be-worth-du
 
Seems to me that folks are too easily choosing to ignore or explain away the downside risk here. Some of the years and AAVs being mentioned, even if considered to be a “discount”, make me nervous.
 
Consider the work Brian MacPherson did to sketch out what a Lester extension might look like given the FanGraphs worldview of the current market -- not necessarily the world of Ruben Amaro signings, but the one where contracts are considered based on expected value:
 
Plugging Lester into the formula, the Red Sox could come to terms with Lester on a four-year deal worth $83.3 million or a five-year deal worth $97.8 million.
 
Again, consider that the above should be viewed as a market-rate contract for a pitcher in free agency, not one who is under contract for another year and who has expressed an interest (willingness? desire?) to take a discount in order to stay in in Boston.
 
So, let’s consider what a discounted deal might look like (baseline assumes $6MM/win, a .5 win decline each season, 5% salary inflation). A simple 3-2-1 weighting of the last three years' WAR produced the same 3.8 WAR projection for next year that ZIPS came up with to use as a baseline moving forward, so that's what you see here (rather than the rounded up 4.0 WAR MacPherson started with in his piece)...
 
  [tablegrid= Lester ]YEAR WAR AAV 2014 3.8  $22.8   2015 3.3  $20.8   2016 2.8  $18.5   2017 2.3  $16.0   2018 1.8  $13.1 [/tablegrid]
 
Consider that, then, to be the "market" for wins, as projected over the next five years and applied to Lester's expectations. Six years seems just crazy to me, so let's focus on four and five year deals, and see what we've got:
 
4/$78.1
5/$91.3
 
Again, using the assumptions laid out above, that's what we could expect a Lester deal could be worth assuming free agent market prices. Alas, Lester has said he's not interested in holding out for that type of contract -- "I understand you're going to take a discount to stay. Do I want to do that? Absolutely."
 
So, about that discount, what could we reasonably hope for and/or expect?
 
Just a quick look at a few different scenarios, applying a range of different discounts to the "market rate" baseline above:
 
[tablegrid= Possible Lester Discounts? ]4 years 5% discount  $74.2   5 years 5% discount  $86.7         4 years 10% discount  $70.3   5 years 10% discount  $82.1         4 years 15% discount  $66.4   5 years 15% discount  $77.6         4 years 20% discount  $62.5   5 years 20% discount  $73.0         4 years 25% discount  $58.6   5 years 25% discount  $68.4 [/tablegrid]
 
But wait...there's more! What type of discount have other pitchers who had expressed a desire to take a hometown discount actually signed for when they carried through on their stated desire?
 
A few years ago, Jered Weaver signed 5 year/$85M extension with LAA over the objections of his agent, Scott Boras. What type of discount did he take?
 
Using the same method outlined in the first table, let's look at what the market for Weaver contract could have reasonably looked like using his projections at the time (in this case, however, give that it was a few years ago I marked the value of a win at $5M, rather than $6M)...
 
[tablegrid= Jered Weaver ]JW WAR JW AAV 5.4  $27.0   4.9  $25.7   4.4  $24.2   3.9  $22.6   3.4  $20.7 [/tablegrid]
 
So...
 
4/$99.6
5/$120M
 
Instead he signed a deal worth 5/$85M -- a thirty percent discount on what he reasonably could have expected to achieve via free agency.
 
So, what would a Lester contract look like if he gives the Sox the same hometown discount that Weaver gave the Angels?
 
[tablegrid= Lester Weaver Discount ]4 years Weaver discount  $55.2   5 years Weaver discount  $64.5 [/tablegrid]
 
The different tables and projection took a little tinkering, but I think my math carried through for each. In any event, I tried to show my work, so tweak as you see fit.
 

Hoplite

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Oct 26, 2013
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Hairps said:
Speier, as usual, does a great job looking at a potential Lester extension:
 
http://www.weei.com/sports/boston/baseball/red-sox/alex-speier/2014/01/27/life-after-30-what-will-jon-lester-be-worth-du
 
Seems to me that folks are too easily choosing to ignore or explain away the downside risk here. Some of the years and AAVs being mentioned, even if considered to be a “discount”, make me nervous.
 
Consider the work Brian MacPherson did to sketch out what a Lester extension might look like given the FanGraphs worldview of the current market -- not necessarily the world of Ruben Amaro signings, but the one where contracts are considered based on expected value:
 
 
Again, consider that the above should be viewed as a market-rate contract for a pitcher in free agency, not one who is under contract for another year and who has expressed an interest (willingness? desire?) to take a discount in order to stay in in Boston.
 
So, let’s consider what a discounted deal might look like (baseline assumes $6MM/win, a .5 win decline each season, 5% salary inflation). A simple 3-2-1 weighting of the last three years' WAR produced the same 3.8 WAR projection for next year that ZIPS came up with to use as a baseline moving forward, so that's what you see here (rather than the rounded up 4.0 WAR MacPherson started with in his piece)...
 
  [tablegrid= Lester ]YEAR WAR AAV 2014 3.8  $22.8   2015 3.3  $20.8   2016 2.8  $18.5   2017 2.3  $16.0   2018 1.8  $13.1 [/tablegrid]
 
Consider that, then, to be the "market" for wins, as projected over the next five years and applied to Lester's expectations. Six years seems just crazy to me, so let's focus on four and five year deals, and see what we've got:
 
4/$78.1
5/$91.3
 
Again, using the assumptions laid out above, that's what we could expect a Lester deal could be worth assuming free agent market prices. Alas, Lester has said he's not interested in holding out for that type of contract -- "I understand you're going to take a discount to stay. Do I want to do that? Absolutely."
 
So, about that discount, what could we reasonably hope for and/or expect?
 
Just a quick look at a few different scenarios, applying a range of different discounts to the "market rate" baseline above:
 
[tablegrid= Possible Lester Discounts? ]4 years 5% discount  $74.2   5 years 5% discount  $86.7         4 years 10% discount  $70.3   5 years 10% discount  $82.1         4 years 15% discount  $66.4   5 years 15% discount  $77.6         4 years 20% discount  $62.5   5 years 20% discount  $73.0         4 years 25% discount  $58.6   5 years 25% discount  $68.4 [/tablegrid]
 
But wait...there's more! What type of discount have other pitchers who had expressed a desire to take a hometown discount actually signed for when they carried through on their stated desire?
 
A few years ago, Jered Weaver signed 5 year/$85M extension with LAA over the objections of his agent, Scott Boras. What type of discount did he take?
 
Using the same method outlined in the first table, let's look at what the market for Weaver contract could have reasonably looked like using his projections at the time (in this case, however, give that it was a few years ago I marked the value of a win at $5M, rather than $6M)...
 
[tablegrid= Jered Weaver ]JW WAR JW AAV 5.4  $27.0   4.9  $25.7   4.4  $24.2   3.9  $22.6   3.4  $20.7 [/tablegrid]
 
So...
 
4/$99.6
5/$120M
 
Instead he signed a deal worth 5/$85M -- a thirty percent discount on what he reasonably could have expected to achieve via free agency.
 
So, what would a Lester contract look like if he gives the Sox the same hometown discount that Weaver gave the Angels?
 
[tablegrid= Lester Weaver Discount ]4 years Weaver discount  $55.2   5 years Weaver discount  $64.5 [/tablegrid]
 
The different tables and projection took a little tinkering, but I think my math carried through for each. In any event, I tried to show my work, so tweak as you see fit.
 
Tremendous work by you and Speier. All kinds of interesting stuff. The Lester/Weaver comparison was eye opening as far as how below market Weaver signed, I'd be happy with a 5-10% discount based on how we can reasonably expect to him to perform in the future.
 

Mike F

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Does the 20% maximum reduction rule apply here?
 

Niastri

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Homar said:
I confess that I'm having a hard time overcoming the emotional hurdle of $20M annually.  Since the first A-Rod contract with Texas, $20M+ contracts have been the province of the truly exceptional, the once in a generation player.  Now, however, with the huge infusions of new TV money, we're going to see more and more high quality players shoot past this threshold.  The teams have the money, they're competitive, and they are willing to pay for the upgrade in wins.  Increasingly it appears rational to pay for a larger pool of players what used to be thought of as exceptional money.  When I'm in my rational mind, I have no problem with Jon Lester being worth $20-22M AAV.  I think the performance justifies it.  I can still hear the little voices in my head that say Lester?  Lester?  $22M for Lester?  But they've not adjusted to the new market.
 
Is anyone hearing discussion about raising the $189M luxury tax line?  As more teams get silly TV money, it won't belong before the teams bumping up against that limit are in double digits, and it'll be harder to restrain themselves, especially as they try to compete.  I know the small market teams would object; but the players are not going to want to hang onto a system which has rich clubs paying in taxes to the poor ones salaries that could be going to players.  Will this be a part of the next CBA negotiations?
 
 
This is the exact purpose of the current salary cap.  They couldn't reduce the overall salaries of the players, but they could put a (at the time) very high cap on salaries that wouldn't affect many of the teams.  Everybody agrees to it because only the Yankees get hurt... Then inflation sits in and all of a sudden, the salary cap is affecting some larger number of teams, and the average salaries of the teams is much closer to the cap than ever before. 
 
The salary inflation is going to continue to increase at a faster rate than the cap, until such time it is a true cap.
 

ehaz

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Sep 30, 2007
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Homer Bailey is reportedly on the verge of a 6/$100 extension with the Reds.  Also in his walk year, perhaps he provides a template for contract talks?  Bailey's slightly younger, and doesn't have the extended track record of success that Lester has but his last two years have been pretty solid as he's actually out pitched Lester (sans post-season).  Thoughts?
 

The Boomer

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ehaz said:
Homer Bailey is reportedly on the verge of a 6/$100 extension with the Reds.  Also in his walk year, perhaps he provides a template for contract talks?  Bailey's slightly younger, and doesn't have the extended track record of success that Lester has but his last two years have been pretty solid as he's actually out pitched Lester (sans post-season).  Thoughts?
Hometown discount?  How about 3 years at $20 million followed by 2 years at $15 million? That's the kind of contract that anticipates some decline with age and frees up some money to bolster the pay of one or two of those pitching prospects who turn out to be in their long term plans in 3 more seasons.
 

terrisus

formerly: imgran
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The Boomer said:
Hometown discount?  How about 3 years at $20 million followed by 2 years at $15 million? That's the kind of contract that anticipates some decline with age and frees up some money to bolster the pay of one or two of those pitching prospects who turn out to be in their long term plans in 3 more seasons.
Unless it's done as two separate contacts, the AAV for luxury tax purposes would be the same for each year regardless of the yearly salary.
 

jimbobim

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We don't know exactly how much Bailey's new deal will break the 100 mill mark but its supposedly 6 for 100 plus. I assume it will take something similar  to get Lester on the dotted line and I would be perfectly content with that level of commitment.  
 
Is he inconsistent during the regular season ? Yes 
Does he seem to have a comfort level with Farrell that could help with the consistency issues ? I would say Yes. 
Are you comfortable rolling out a rotation of Clay, Lackey, Doubront and two of the prospects next year ? No. 
Can this team afford Lester regressing to an average or below average pitcher on the backend of the deal in exchange for an elite playoff quality SP number 2 or 1 for the first 3 years of the deal ? Yes 
 
Get it done. 
 

koufax32

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Red(s)HawksFan said:
Opening Day.
I read somewhere that no discussions have taken place. That's obviously not to be taken as fact but it would put a small hole in the conspiracy theorist approach. On my phone so can't link but I believe this was in the globe.
 

pdub

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5yr/$110M - does this get it done? Gets a bit more than Bailey received, can still land one more short-term deal after this one expires if he's still durable. 
 

benhogan

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pdub said:
5yr/$110M - does this get it done? Gets a bit more than Bailey received, can still land one more short-term deal after this one expires if he's still durable. 
No thanks. Thats way too much for Lester..
 
Really like the work Hairps did upthread, please check that out.  Think that runs along the lines of how Sox mgmt would approach Lester.
 
Would also like to see, using Spier/Hairps methodology, what kind of discount Pedroia took?  Probably not as much as Weaver. Lester's extension would be shorter then Pedroias', so I'd expect his discount to be less.
 

jimbobim

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I think its unreasonable to think Lester will take a discount all the way down to the 55-65 million range. He's clearly more valuable than Ubaldo who just got 50 mill over 4 years at 30. 
 

benhogan

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jimbobim said:
I think its unreasonable to think Lester will take a discount all the way down to the 55-65 million range. He's clearly more valuable than Ubaldo who just got 50 mill over 4 years at 30. 
I don't think anyone here suggested Lester would be offered or accept a' Weaver type' discount/deal (esp since wins costed less then).
 
I agree with Hoplite that a 5-10% discount (16-17MM/yr) would be a reasonable amount for both sides.
 

LondonSox

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You guys may prove to be right but I think you are massively underestimating the trend in player contracts. Any deal done now with a mild discount to free agency will look hilarious in a couple of years.
If you want him sign him, if you don't so be it. Waiting is just going to make it look worse because every contract for good players locked up is going to be higher.
 
Look at that contract Ubaldo just signed! He's going to sign for 1 million and change more/ year than him coming off a world series win and wonderful postseason? 
 

gammoseditor

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I can't tell if some of the numbers thrown around in this thread include throwing out 2014 or adding it on. If you think 5/100 is the right number does that mean 2014-2018 at 20 per year, or 2014 at his current rate, 13 million, then 2015-2019 at 20 per year? Both seem very high to me. If you mean 2014-2018 you're actually extending him for 4 years at 93 million, or 23.25 per year. 2015-2019 is giving signing him through his age 35 season and a total contract of 6/113.
 
Ubaldo just signed for 12.5/year and is the exact same age as Lester.  Lester has clearly been better.  According to fangraphs he's been just under 1 win per year better the last 6 years.  Let's round up to 1 win and say that win costs 6.5 million on the open market.  That puts him at 19 million compared to Ubaldo's 12.5.  He's also a year away from FA.  Players take less when they are 1 year away from FA in exchange for the risk in underperforming or getting hurt before becoming a FA. 
 
I think a "hometown discount" is 18/year for 2015-2018, so including 2014 his new deal would be 5/85.  As a free agent I could see him getting 5/110 if he has an average Jon Lester year, but he's not a free agent right now and can't negotiate as if he is one.  He has a $13 million salary for 2014. 
 
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