Extending Lester

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Harry Hooper

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Rasputin said:
Am I the only one that thinks a deal is done over the break?
 
Yes.
 
 
No, if Lucchino thinks a 4-year/$76 million offer at that point will close the deal.
 
 
Time to play the Blues.
 

ShaneTrot

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Did anyone listen to Olney and Law discuss this on the ESPN baseball today podcast? One of the things they said about Lester's situation is the Sox have young, cheap and good players all up and down the roster and not one of these guys is expensive yet. If they don't sign Lester (or his replacement) for big money, are they going to be become a 10-15 place team in payroll?
 
My intial rection to the Manny signing was that it was nuts. 2004 and 2007 made me re-think that deal. Obviously, the whole feeding the monster didn't work out in 2011 but I don't feel like watching the Sox go forward relying on all the kids being studs. Sometimes you need to spend money on a guy and take your chances. Is anyone regertting Lackey's deal after 2013?
 

Eddie Jurak

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ShaneTrot said:
Did anyone listen to Olney and Law discuss this on the ESPN baseball today podcast? One of the things they said about Lester's situation is the Sox have young, cheap and good players all up and down the roster and not one of these guys is expensive yet. If they don't sign Lester (or his replacement) for big money, are they going to be become a 10-15 place team in payroll?
 
They traded Adrian Gonzalez, Josh Beckett, and Carl Crawford for prospects and filler, did not sign any big ticket free agents, and kept their payroll well above 10-15.
 

Rasputin

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Eddie Jurak said:
They traded Adrian Gonzalez, Josh Beckett, and Carl Crawford for prospects and filler, did not sign any big ticket free agents, and kept their payroll well above 10-15.
Yeah, because they had to fill in half the roster with free agents. If they don't sign Lester or a FA replacement, they'll have players making chump change at third, short, center, catcher, two rotation spots, and probably at least one bullpen slot.

With right, first, DH,and three rotation spots already spoken for, you would have to spend a hell of a lot on left, the bullpen, and the bench.
 

Darnell's Son

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Rasputin said:
Am I the only one that thinks a deal is done over the break?
 
Absent a deal for Stanton or some other salary eater, I don't see how the team can allow Lester to sniff free agency.
 

Savin Hillbilly

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Darnell's Son said:
 
Absent a deal for Stanton or some other salary eater, I don't see how the team can allow Lester to sniff free agency.
 
I don't think it's really up to them at this point.
 
 
ShaneTrot said:
If they don't sign Lester (or his replacement) for big money, are they going to be become a 10-15 place team in payroll?
 
Maybe for a couple of years. Remember, if these kids pan out, we'll need to lock them up for decent money, and if they don't, we'll need to go get somebody who will.
 
I just hope to god Cherington isn't thinking the way some people around here clearly are, "OMG! We've only got $100M committed for next year! Quick, find somebody to spend some money on!" Money doesn't win championships. Good acquisitions win championships. Money broadens the range of possible good acquisitions, but you don't spend the money just to spend the money.
 

glennhoffmania

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snowmanny said:
 
 
Apologies if I misrepresented anyone's point of view.  There are a bunch in the under 15-19 Million camp, and a couple in the very high range (including me), but the general consensus seems to be that a signing at 5/100 or perhaps slightly above would make most of the board happy and is generally expected.
 
Sure, but is there a team that wouldn't sign Lester for 5/100?  Like it or not, we can't keep comparing the situation to the Weaver, Sanchez, and Wainwright deals.  The market has changed.  Kershaw just got 7/215, Verlander got 7/180, Tanaka got 7/155 before throwing a pitch, and Scherzer was offered 6/144.  Even if one thinks that all of those pitchers are better than Lester, why in the world would he settle for 5/100, or about 31% less than Scherzer's offer and about 35% less than Tanaka's deal?
 
I think that 6/120 is the starting point and 6/132 is Lester's realistic floor.
 

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Savin Hillbilly said:
 
I don't think it's really up to them at this point.
 
 
 
Maybe for a couple of years. Remember, if these kids pan out, we'll need to lock them up for decent money, and if they don't, we'll need to go get somebody who will.
 
I just hope to god Cherington isn't thinking the way some people around here clearly are, "OMG! We've only got $100M committed for next year! Quick, find somebody to spend some money on!" Money doesn't win championships. Good acquisitions win championships. Money broadens the range of possible good acquisitions, but you don't spend the money just to spend the money.
I agree to a certain extent but if the Sox are going to start to act like they are the Kansas City Royals and still be the most expensive ticket in the game, I will be pissed.You have to pay for the wins in some way, either by having exceptional cheap talent or good, expensive vets. Obviously, the best teams are a blending of both. I think the 2007 team was a perfect example, some high-priced talent and good young players like Pedroia, Ellsbury, and Papelbon.
 

Plympton91

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ShaneTrot said:
I agree to a certain extent but if the Sox are going to start to act like they are the Kansas City Royals and still be the most expensive ticket in the game, I will be pissed.You have to pay for the wins in some way, either by having exceptional cheap talent or good, expensive vets. Obviously, the best teams are a blending of both. I think the 2007 team was a perfect example, some high-priced talent and good young players like Pedroia, Ellsbury, and Papelbon.
 
The problem is, if the Red Sox reduce face value ticket prices they're just sacrificing more revenue to the legal and illegal resale markets.
 
Maybe they make a run at Max Scherzer if they are spurned by Lester.  Scherzer is similar age but has a lot less mileage on his arm.
 

3_games_down

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ShaneTrot said:
Did anyone listen to Olney and Law discuss this on the ESPN baseball today podcast? One of the things they said about Lester's situation is the Sox have young, cheap and good players all up and down the roster and not one of these guys is expensive yet. If they don't sign Lester (or his replacement) for big money, are they going to be become a 10-15 place team in payroll?
 
Money is a motivating factor for young, cheap, and well performing players, of that I am sure. I'm less sure if I get this low ball approach to the Lester extension talks. Could these negotiations end up a pyrrhic victory? I'm of the opinion that the front office's approach to the Lester extension talks sends the wrong message to the rising stars in the organization and those they wish to court via the draft. Long term I think the Red Sox lose leverage in future extension talks.       
 

Rovin Romine

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Savin Hillbilly said:
 
 Remember, if these kids pan out, we'll need to lock them up for decent money, and if they don't, we'll need to go get somebody who will.
 
I just hope to god Cherington isn't thinking the way some people around here clearly are, "OMG! We've only got $100M committed for next year! Quick, find somebody to spend some money on!" Money doesn't win championships. Good acquisitions win championships. Money broadens the range of possible good acquisitions, but you don't spend the money just to spend the money.
 
Yep.   I'm surprised how quickly people forget (2012) the difference between an excellent player at a premium price and a merely good player at a premium price.  Assuming the free agent market stays competitive out there, one or two bloated contracts can really drag down a club, in terms of those player's performances, blocking more talented younger players, and hamstringing the club in terms of new FA signings.  This gets magnified if the club suffers injuries elsewhere on the diamond.
 
If the Sox are comfortable valuing Lester at well below what he'll get on the FA market, then I'm fine with him going elsewhere.  
 

Plympton91

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Rovin Romine said:
 
 the difference between an excellent player at a premium price and a merely good player at a premium price.  
 
Can you tell difference ex ante?
 
Can the Red Sox? 
 
Was the Lackey contract a good one or a bad one?  Do the Red Sox win the world series in 2013 without Lackey's 3-something ERA?  Or, without Lackey's 6-something ERA, do they win the world series in 2011 and the whole history of 2012 is different?  Maybe Lackey's piss-poor 2011 doesn't matter anyway if Buchholz stays healthy and Bard doesn't implode in September, those had absolutely nothing to do with the contracts given to Gonzalez, Crawford, or Lackey; may have had something to do with picking the cheaper Bobby Jenks over the more expensive Scott Downs or Juaquin Benoit though, if Bard's ineffectiveness was due to overwork--but given what we now know, that seems unlikely.
 
Likewise, a big problem for the Red Sox in 2011, which led to 2012, was that JD Drew was essentially finished as a ballplayer in 2010.  Does that mean they shouldn't have signed JD Drew?  Are you willling to risk 2007 on that conclusion?  But, was the flameout of Drew one year too soon really such an insurmountable problem?  Or was the coincident nearly catastrophic injury to Ryan Kalish, who would have been a fine piece of depth for RF, the problem?  Or, was the problem that the Red Sox stuck with a clearly offensively and defensively struggling Josh Reddick (.244 / .293 / .389) throughout August/September, rather than call up Daniel Nava, who hit .301 / .391 / .470 over the final 3 months of the Pawtucket season and then .275 / .388 / .427 in major leagues in the first half of 2012?
 
Does Matsuzaka's flame-out mean the Red Sox were absolutely correct to bow out early on Yu Darvish and Masuhiro Tanaka? (And Ryu).
 

soxhop411

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Mlbtraderumors explains
by MARK POLISHUK | MAY 5, 2014
The recent struggles of Yankees starters C.C. Sabathia (age 33) and Hiroki Kuroda (age 39) weigh on the minds of Red Sox management in regards to a possible Jon Lester extension, Peter Gammons tweets. While the Sox are surely interested in keeping Lester in the fold through 2018, anything beyond that could be problematic given the history of guaranteeing big money to aging pitchers. Lester would be 35 on Opening Day 2019, which could be why Boston’s most recent offer to the southpaw was a four-year extension.
 

Plympton91

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soxhop411 said:
Mlbtraderumors explains
by MARK POLISHUK | MAY 5, 2014
The recent struggles of Yankees starters C.C. Sabathia (age 33) and Hiroki Kuroda (age 39) weigh on the minds of Red Sox management in regards to a possible Jon Lester extension, Peter Gammons tweets. While the Sox are surely interested in keeping Lester in the fold through 2018, anything beyond that could be problematic given the history of guaranteeing big money to aging pitchers. Lester would be 35 on Opening Day 2019, which could be why Boston’s most recent offer to the southpaw was a four-year extension.
 
I don't see why C.C. Sabathia is a comp at all given his early-career reliance on elite velocity and his only recent attention to the damage to his longevity associated with his pre-weight-loss body type.  A 6-year extension would take him to age 37, an age at which Kuroda was fantastic for the Yankees. Andy Pettitte, who Lester is better than, showed almost no deterioration from age 31 to 37.
 
Sadly this strikes me as early round of damage control from a front office that knows its not going to resign a still-very-good pitcher.
 

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It's all coming from Gammons.  Why are we putting any stock in it at all?  I know he was great once upon a time, but he lost his fastball long ago.  Not to mention his inside man in the Sox FO has been in Chicago for the last three years.
 

wade boggs chicken dinner

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Plympton91 said:
 
Can you tell difference ex ante?
 
Of course no one can tell the difference, which is why - I presume the RS brass would say - you don't give seven year contracts to players in their 30s.
 
Which is also why Papelbon (different length but similar reasoning) and Ellsbury left; Lester will be leaving, and Buchholz probably will as well. 
 
If I can count correctly (no guarantees there), on a list of teams ranked by the salary of their highest-paid player, the Red Sox came in middle of the pack (somewhere around 15th, tied with the Rangers).  I think that is precisely where they would like to be, which will depend greatly on them being able to draft and develop exceptionally well.
 

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soxhop411 said:
“@pgammo: Bosox ownership sees Sabathia/Kuroda lose 4 on homestand(19.1 IP, 36 H, 18 ER) in Lester scope, but think 2015--18 w/out him...not good”


https://twitter.com/pgammo/status/463269411793936384
 
This is pretty idiotic on multiple levels.  Comparing 3 totally different pitchers, using a small sample, ignoring the value he could provide in the first 4 years, to name a few.
 

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glennhoffmania said:
 
This is pretty idiotic on multiple levels.  Comparing 3 totally different pitchers, using a small sample, ignoring the value he could provide in the first 4 years, to name a few.
 
I think the "2015-18 w/out him...not good" addresses the value he could provide in the first four years.
 

wade boggs chicken dinner

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Papelbon's Poutine said:
 
I disagree with most of this. 
 
Papelbon left because you don't invest that much in years or dollars in a reliever. Ellsbury left because they learned their lesson that that type of player isn't worth $23M per year over any term. Clay will leave because you don't commit to a SP that has never given you more than 189 IP. 
 
Where they rank on a list of highest paid player is irrelevant and I don't think they really care about it. They want value for their dollar and when the right player comes along, they will spend it. They can no longer rely on their financial advantage to help in the draft or international market. So if they are relying on drafting and developing better than every other team and content with that being their primary advantage, then they are either being extremely arrogant or extremely foolhardy. 
 
I'm not sure what you are disagreeing with.  They didn't pay Papelbon because they didn't want to give money/years to that type of player.  They didn't pay Ellsbury because they didn't want to give money/years to that type of player.  They aren't going to pay Lester because they don't want to give money/years to that type of player, and they are not going to pay Buchholz for the same reason.  While the specifics may vary slightly, the reasoning is still the same.
 
Which I believe I said originally.
 
Not having the highest paid player in the game is indicative of one thing - not being in the FA market and giving top $ contracts.  Which it sounds like the Red Sox are comfortable with.  For example, Xander will get paid, but they'll do it as they have in the past - buy out some arb years and a FA year or two to give him financial security.  But he won't be one of the top players in the game, at least for a while.
 
As for the rest, I also agree with you (as I've said in other posts but did not say in this one).  The one comment I'll make is that I think the FA market is even tougher to find value than the international/draft market, so if they think that they can better build a team by foregoing the FA market except for short deals at reasonable prices, and use the extra draft picks that they will get from losing Type A free agents to give them an advantage to team-building, well at least
I understand their thinking.  Hopefully they can pull it off.
 

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soxhop411 said:
“@pgammo: Bosox ownership sees Sabathia/Kuroda lose 4 on homestand(19.1 IP, 36 H, 18 ER) in Lester scope, but think 2015--18 w/out him...not good”


https://twitter.com/pgammo/status/463269411793936384
 
The only thing I take from that is the Yankees are going to need another starting pitcher next year. 
 
St. Louis was 11th in payroll last year. They have an organization that I assume most people on this board would be thrilled to replicate.
 

curly2

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One huge difference is the Cardinals have an ace in Wainwright tied up through 2018 and a possible young ace in Wacha. The Sox have a lot of good young pitching prospects but I don't think any has Wacha's ceiling.
 

ivanvamp

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curly2 said:
I think the "2015-18 w/out him...not good" addresses the value he could provide in the first four years.
I'm wondering if it's more this: they see the struggles of those guys and it makes them more certain that NY will go after Lester.
 

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kieckeredinthehead said:
 
The only thing I take from that is the Yankees are going to need another starting pitcher next year. 
 
St. Louis was 11th in payroll last year. They have an organization that I assume most people on this board would be thrilled to replicate.
The Cards are a very well-run franchise, but I would argue the bar is lower for St. Louis. Being 10th in MLB is usually the most spending in their division, or close. I mean, the Blue Jays spent more than they did last year.
 
Last year St Louis won 97 games; they were excellent. But the years before that: 88, 90, 86, 91, 86, 78, 83. They got 4 playoff appearances out of those last 7 years but if you adjust for tougher competition that looks like a lot of just missing in the AL. With the new playoff system are we happy with a coin flip and then hoping to go on a run or do we want to win the division?
 

Eddie Jurak

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soxhop411 said:
“@pgammo: Bosox ownership sees Sabathia/Kuroda lose 4 on homestand(19.1 IP, 36 H, 18 ER) in Lester scope, but think 2015--18 w/out him...not good”


https://twitter.com/pgammo/status/463269411793936384
e.e. gammings:
 
  • John Lackey, infected forehead, who used to, throw a tomatosmooth-plum curveball, and break sixfivefour batsjustlikethat, go. He was a humble man, and what i want to know is, how do you like this determination now, Boston.
 

wade boggs chicken dinner

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Papelbon's Poutine said:
 
 
I disagree with you making a blanket statement like "you don't give 7 year contracts to players in their 30s".
 
* * * *
 
You very well may be right, but it's nothing but conjecture to assume they have made an organizational mandate to avoid said deals.   
 
While I admit it's speculation on my part, surmising that there might be an organizational philosophy not to give 7-year contracts to players in their 30s is more than sheer conjecture.  There are two quotes from this article - http://www.businessweek.com/printer/articles/196587-john-henry-and-the-making-of-a-red-sox-baseball-dynasty (BTW, this was discussed in another thread too) - that suggests the Sox may have this philosophy in place.
 
First:  "The Collapse left Red Sox Nation sullen and traumatized. Henry was repentant. “We had a certain discipline for the first five or six years that really paid big dividends, and we got away from that,” he says. “We learned a lesson in ever-growing, long-term contracts with free agents."
 
Second:  "In “Can’t Buy Much Love: Why Money Is Not Baseball’s Most Valuable Currency,” Martin Kleinbard arrives at a conclusion that mirrors Henry’s own thoughts about where the true value lies in baseball today. Kleinbard finds a weak correlation between payroll disparity and winning, arguing instead that “youth dominance”—a team’s reliance on younger, cheaper players not yet eligible for free agency—has become a much stronger predictor of success. “To me, the most important thing this study shows is that virtually all of the underpaid players are under 30 and virtually all the overpaid players are over 30,” says Henry. “Yet teams continue to extravagantly overpay for players above the age of 30.”"
 
So while yes, I'm sure that if the Sox were offered the right player at the right price (probably a discount), they would shell out a 7-year contract.  But they aren't going to be winning any bidding wars any time soon, and because of that, I think it's rather easy to read the tea leaves w.r.t. Lester and Buchholz when he gets to the market as well.
 

Rovin Romine

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Plympton91 said:
Can you tell difference ex ante?
 
Can the Red Sox? 
 
I think they can. How many in-house FA's have the Sox real reason to regret passing on? Damon? Lowe?

How many FA's we're let go in a timely manner? (The vast majority.)

Now how many were wrongly retained? Lowell? Schilling?

No club is perfect on FA spending. But the Sox have done OK with their in house FA's.
 

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Toe Nash said:
The Cards are a very well-run franchise, but I would argue the bar is lower for St. Louis. Being 10th in MLB is usually the most spending in their division, or close. I mean, the Blue Jays spent more than they did last year.
 
Last year St Louis won 97 games; they were excellent. But the years before that: 88, 90, 86, 91, 86, 78, 83. They got 4 playoff appearances out of those last 7 years but if you adjust for tougher competition that looks like a lot of just missing in the AL. With the new playoff system are we happy with a coin flip and then hoping to go on a run or do we want to win the division?
 
You're right, the Blue Jays did spend more than the Cardinals last year. I'd rather be a Cardinals fan.
 
Over the time span you quote (2006-2013), the Cardinals averaged 87 wins per year. The Red Sox averaged 89. The Cardinals made the playoffs five times, winning the WS twice. The Red Sox made the playoffs four times, winning the WS twice. 
 
There are three models for success over the past decade. Oakland and Tampa have excellent farm systems, and are able to trade high ceiling guys for solid veterans. They sign bargain bin free agents and then trade them to re-stock their farm. They rarely, if ever, retain their own players past arbitration. The St. Louis Cardinals and Boston Red Sox have relied on a combination of a strong farm system, team-friendly deals for younger stars, and supplementing each year with mid-level free agents to either make-good, one year contracts or the ever-present 3/13. And the final strategy is to be the New York Yankees. The Red Sox can't be the New York Yankees. 
 
R^2 value between payroll and winning percentage is about .24.
 

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Debate about whether the Red Sox are going about the Lester negotiations is all well and good. But can't we at least reject the idea that they this is part of a nefarious plan to cut payroll? It seems like I have been reading about this for 12 years, and they have had a top 3 payroll basically every year.

I believe the Red Sox front office is trying to figure how to spend their money, not whether to spend it.
 

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Agreed, Lahoud.  They extended Pedey with then-record-setting money for a 2d baseman.  Reupped with Nap even though it cost more than their original deal.  Have spent a little extra on vets to develop their deep depth (Gomes, Uehara, Ross) rather than simply going with youth or the cheapest options.  So simply realizing that huge long term deals for guys well into their 30s is a clearly bad risk overall doesn't mean they won't still spend.  They'll just try to spend more wisely.  With 3 recent titles in the books, I'm fine with that.  (Although I do still think there's time and room for them to find a middle ground with Lester on a Wainwright-sized deal...)
 

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snowmanny said:
Here are the suggested offers that I found in this thread: 15M/year(FanSinceBoggs); 5/100 "is the floor" (bombdiggz); 16.5Mx5-6 yrs (Papi's Fan); 5/100-110 but that's probably not enough (Ed Hillel); 6/100 (Maufman); 6/120 (jimbobim); FO will offer 16-18Mx4-5 yrs (C4CRVT, who seems to have been correct); "his market starts at 6/120-130"; 5-6 years @20-25M (bankshot); 4/80 "is a good starting point" (Stanley Steamer); under 6/120 (Toe Nash); 5/100 (Beantownldah); 6/120 (ivanvamp); 5/110 (Morgan's Magic Snowplow); 5/90, later amended to "between 5/100 and 6/150" (koufax37); 5/100-6/120 (keninten); 6/111 (Drek717); "Near Scherzer's"rejected offer of 6/144 (me, in a fit of generosity with other people's money); 5/90 (radsoxfan); 5/90 or 6/105 or 6/112 (Plympton91);5/90 in one post,  would "consider" 5/120 in another (The Boomer); 6/125 (FredCDobbs) 5/90-100 (Savin Hillbilly); 5/100 (Minneapolis Millers); 17-18AAV (Yaz$Ever); 5/100 (DennyDoyle'sBall; 5/100 (JoshV02); 5/80 (Hoplite); worth 5/100, maybe takes 5/80 (Sampo Gida); 5/100 (donut ogre); 6/110 (Apisth); 5/110 (pdub) 16-17AAV (benhogan); 5/85 is homedownt discount and 5/110 is FA value (gammoseditor); 5/100 pokey_reese; 5/100 (nvalvo); 6 years, seems to suggest 6/120 (glenhoffmania); 5/110 (Doctor G); 5/100 (Rudy Pemberton).
 
Apologies if I misrepresented anyone's point of view.  There are a bunch in the under 15-19 Million camp, and a couple in the very high range (including me), but the general consensus seems to be that a signing at 5/100 or perhaps slightly above would make most of the board happy and is generally expected.
 
Thanks for the summary.  I think the window of him signing for anything considered a value contract have passed.  I still see him in the 5/100 to 6/150 range, but definitely see him drifting up that range.  He has shown a remarkable upswing to both his command and his dedication to his craft (which a year ago as one of his detractors I didn't expect), and those factors give every indication that he will be an excellent pitcher over the next multiple seasons in addition to being durable.  Add in exceptional performance last October and 15K/1H performance stuff this spring, and in his mind and at least one other club he will be worth a lot.
 
I know he has indicated he wants to stay, but if negotiations are really tabled until after the season and 4/75 was really a place the front office felt as a Spring Training top offer, we are definitely entering into a Robinson Cano situation (wanted to stay with the Yankees who despite deep pockets didn't come close to years/dollars of another offer).  I still think he should be a priority, but as he peaks in perceived performance just as we get to him on the open market, I think he will likely end up with a Winner's Curse level offer that we won't meet, and we probably will regret not making a 5/115 or 6/135 offer this spring that might have gotten it done.
 

Plympton91

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I'm still thinking about this comparison of Lester to Sabathia and Kuroda.
 
Why aren't Glavine and Jamie Moyer comps?  Would they feel more inclined to extend Lester if he was successful by living on the edge of the zone with offspeed pitches?  Isn't Andy Pettitte universally considered a very close comp for Lester?  He showed almost no deterioration through his mid-30s; although, perhaps the Red Sox think he had more consistent "help" than he copped too?  Kenny Rogers, after escaping his disaster in pinstripes at age 31-32, was successful and durable from age 33 through his age 41 season except for a single season blip at age 36.   David Wells showed nothing more than typical variation in his performance from age 30 to 42.
 
I'm sure they've got Sabermetricians doing comprehensive studies, and PECOTA projections are probably the best purely statistical tool for an unbiased though imperfect assessment, but to focus on Sabathia and Kuroda seems absurd. That's just someone in the front office putting out an excuse to Gammons.
 

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Plympton91 said:
I'm still thinking about this comparison of Lester to Sabathia and Kuroda.
 
Why aren't Glavine and Jamie Moyer comps?  Would they feel more inclined to extend Lester if he was successful by living on the edge of the zone with offspeed pitches?  Isn't Andy Pettitte universally considered a very close comp for Lester?  He showed almost no deterioration through his mid-30s; although, perhaps the Red Sox think he had more consistent "help" than he copped too?  Kenny Rogers, after escaping his disaster in pinstripes at age 31-32, was successful and durable from age 33 through his age 41 season except for a single season blip at age 36.   David Wells showed nothing more than typical variation in his performance from age 30 to 42.
 
I'm sure they've got Sabermetricians doing comprehensive studies, and PECOTA projections are probably the best purely statistical tool for an unbiased though imperfect assessment, but to focus on Sabathia and Kuroda seems absurd. That's just someone in the front office putting out an excuse to Gammons.
 
I agree that Sabathia and Kuroda make zero sense as comps.  But I also would question all of the other guys you mentioned.  Pettitte clearly was cheating for at least a portion of his career.  Glavine and Moyer were different types of pitchers.  And in general I'm never sure how useful looking at other players is.  Every pitcher and every situation are different.  The PED environment is certainly different, the economics of the game have changed, and I don't think any of these guys are all that similar to Lester in terms of pitching style. 
 
The bottom line is if they think Lester can/will be worth between three and five wins for the next four years or so I'm stumped why they haven't wrapped this up yet. 
 
Looking at his stats for this year a couple of things jump out at me.  His LOB% is currently the lowest of his career at 65%.  His BABIP is the highest of his career at .328.  But his BB rate, K rate and HR rate are currently career best marks, which explains why his FIP is only a little above 2.  His GB% is also the lowest of his career at 40%.
 
What do all of these numbers mean in the aggregate?  Did he improve his control and learn how to suppress homers?  Is he even better than he's looked because of the low strand rate and high BABIP?  What explains his K rate jumping by about 3 compared to the last 2 years?
 

Apisith

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Going by his best comparisons on baseball reference, assuming a 6 year deal covering ages 31-36 seasons:
 
Millwood: 9.5bWAR, 97 ERA+
Pettitte: 18.5bWAR, 115 ERA+
Beckett: 6.5bWAR with the rest of this season and next season to go, 107 ERA+
Mulder: finished by 28
Lackey: 3.5bWAR with the rest of this season and next season to go, 93 ERA+
 
It just doesn't look good for Lester. The best case scenario is Halladay and even he was done by his age 35 season, and by done I mean he was completely finished, and that was pitching in the NL, too.
 
The Pettitte scenario makes Lester deserving of around $18m/year for 6 years (assuming $5.5m/win with 5% inflation) but that's assuming he doesn't get injured at all. The more you look at it, the more it's obvious why we're focused on not going more than 5 years. I initially posted that I'd be happy with 6/$110m - which is the Pettitte scenario - but I don't think I'd be willing to go more than 5/$92m now. If he reaches free agency, will someone give him more than that? Almost assuredly, but that doesn't mean that we should.
 
He's already shown how bad he is when he 'loses it' and that was in his age 28 season. He's not worth the risk of a long term deal. We got his best years. Let someone else get the worst years.
 
There'll be older SPs out there who we can try the Napoli/Victorino route, guys like Shields and even Peavy if he has a good season with us. It's not Lester or kids or scrubs. There'll be options out there.
 
In 2016, there'll be other pitchers available, guys like Cueto, Chen, Gallardo, Kazmir, Latos, Porcello, Samardzija and whoever breaks out this year and next.
 

yecul

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Besides, we are talking about a pending free agent, not a departed one. If they wind up passing on Lester, then I think there are questions about their general willingness to sign 30+ pitchers to longer deals and/or their opinion of Lester himself.  Right now we know that they extended a long-ish (but low-ish) offer, which was rejected. Unnamed random quotes need to be taken with a grain of salt.
 

Plympton91

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Apisith said:
Going by his best comparisons on baseball reference, assuming a 6 year deal covering ages 31-36 seasons:
 
Millwood: 9.5bWAR, 97 ERA+
Pettitte: 18.5bWAR, 115 ERA+
Beckett: 6.5bWAR with the rest of this season and next season to go, 107 ERA+
Mulder: finished by 28
Lackey: 3.5bWAR with the rest of this season and next season to go, 93 ERA+
 
It just doesn't look good for Lester. The best case scenario is Halladay and even he was done by his age 35 season, and by done I mean he was completely finished, and that was pitching in the NL, too.
 
The Pettitte scenario makes Lester deserving of around $18m/year for 6 years (assuming $5.5m/win with 5% inflation) but that's assuming he doesn't get injured at all. The more you look at it, the more it's obvious why we're focused on not going more than 5 years. I initially posted that I'd be happy with 6/$110m - which is the Pettitte scenario - but I don't think I'd be willing to go more than 5/$92m now. If he reaches free agency, will someone give him more than that? Almost assuredly, but that doesn't mean that we should.
 
He's already shown how bad he is when he 'loses it' and that was in his age 28 season. He's not worth the risk of a long term deal. We got his best years. Let someone else get the worst years.
 
There'll be older SPs out there who we can try the Napoli/Victorino route, guys like Shields and even Peavy if he has a good season with us. It's not Lester or kids or scrubs. There'll be options out there.
 
In 2016, there'll be other pitchers available, guys like Cueto, Chen, Gallardo, Kazmir, Latos, Porcello, Samardzija and whoever breaks out this year and next.
 
I've never really understood the BRef comparisons.  They make for nice conversation, but I don't understand how a righthanded pitcher who spent the early part of his career in the National League can be the number 1 comp for a lefthanded pitcher who spent his whole career in the American League. Lester is also better by pretty much any metric you use:  Through age 30, Millwood had 3 seasons with an ERA+ above 104; whereas, Lester has been above 110 five times by age 30 and seems on pace for a 6th this year. Doing some kind of FIP or SIERRA must also favor Lester:  Lester K/9 of 8.2 vs. Millwood 6.9 despite lots of pitchers in his lineups.  Millwood HR/9 of 1.0 vs. Lester 0.8; GB/FB Millwood .71 to Leser .92 (though it's declined precipitously over the past 3 years); and BB/9 Millwood 2.8 vs. Lester 3.2 
 
And if Millwood is Lester's number 1 comp, why isn't it vice-versa?   Javier Vazquez is Millwood's #1 comp, which actually seems more believable.  Looking at Millwood's comps, you see Frank Viola, who is a much better comp for Lester by any common sense baseball knowledge, yet Frankie doesn't show up at all in Lester's list.  He's also a cautionary tale, being very good and durable until age 33, and then blowing out his arm.
 
I'd ask again, why aren't Tom Glavine and Jamie Moyer considered comps?  David Wells?  Kenny Rogers?  If you look through their lists you see other cautionary tales, like Mike Hampton and Tom Browning, though I think Hampton's problem was basically Coloradoitis.  I'm not looking to cherry pick just the pitchers with long careers, but I think any "similarity score" that doesn't heavily weight what arm the pitcher threw with and what league they spent the majority of their career in is deeply flawed.
 

DennyDoyle'sBoil

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There's a bit of a round peg in a square hole element here.  The Red Sox really need a starter of Lester's quality in the next couple of years, and have plenty of money to pay for it.  Not counting Lester, we have 2.5 starters penciled in, in Lackey, Doubront, and Buccholz.  Webster and Workman look like the next two up, but that rotation plainly needs another top of the rotation guy.  There is plenty of money to pay for pitching next year, given the confluence of cost-controlled younger players and the salary minimum option for Lackey. The Red Sox have minuscule commitments for 2016.  I haven't looked at every team, but it could very well be lowest in the league.  It's a third of that of the Rays.  It's even less than the Royals.
 
If it were the right guy, unless there is a Stanton-like acquisition being considered, I wouldn't have any problem with the Red Sox spending $30 million in each of the next two years for a top of the rotation starter.   They have it to spend in the next two years, can do so without luxury tax implications, and it's definitely a need unless we're all comfortable watching rookies and Doubront sixty percent of time, or more if Clay can't go every five days.  But starting pitching isn't like position players.  For position players, you can go out and get a value guy for 2 years that projects as a 2.0 WAR who you think has a 3.5 upside.  It doesn't work like that with pitching and certainly not left-handed pitching.  If you want to do something for two years or so, then just to get a middle of the rotation guy, you're looking at a guy well into his 30s and upwards of $15 to $20 million a year like Dempster.  And even then, you may have to give up a significant piece to get him, like we did with Peavy.
 
Plus, it goes without saying with respect to all this talk about "30+" guys, but by definition any free agent likely is going to be 30+.   
 
So, let's say the market for Lester is something like 6/132.  Might the Red Sox be in a unique position to front-load a contract like that without serious implications for the next couple of years and without mortgaging the future?  Like 30/30/15/15/15/15?  Yes, $30 million for the next two years for Lester is an overpay.  But it's money that doesn't appear needed elsewhere at the moment and they have it.  And, in years 3 and 4, he likely will be underpaid.  All I'm really getting at is there is a fairly unique spending opportunity here for the Red Sox given the unusual confluence of Lackey's contract and so much cost control at key, expensive positions.  I really can't think of anything better to do with it than on known, proven, top of the rotation starting pitching.
 

glennhoffmania

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DennyDoyle'sBoil said:
So, let's say the market for Lester is something like 6/132.  Might the Red Sox be in a unique position to front-load a contract like that without serious implications for the next couple of years and without mortgaging the future?  Like 30/30/15/15/15/15?  Yes, $30 million for the next two years for Lester is an overpay.  But it's money that doesn't appear needed elsewhere at the moment and they have it.  And, in years 3 and 4, he likely will be underpaid.  All I'm really getting at is there is a fairly unique spending opportunity here for the Red Sox given the unusual confluence of Lackey's contract and so much cost control at key, expensive positions.  I really can't think of anything better to do with it than on known, proven, top of the rotation starting pitching.
 
Front loading a deal doesn't make sense for a team.  The AAV doesn't change so the luxury tax implications don't change.  Economically it makes no sense.  If it'll take 6/120 to sign him there's no advantage in paying him 30m in the first two years.  The only caveat would be if he's willing to take less money on a present value basis to have it front loaded, but that wouldn't make sense for him either and I'm sure his advisors understand that.
 

Apisith

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ERA+ is park and league adjusted so it's the best metric to judge a pitcher, for me. Lester's ERA+ has been trending down for six years with only last year being a minor bump. He's clearly an ace when he's on but he's had long, long periods of inconsistency - a whole season, in fact - and who knows what the FO know about the health of his arm and shoulder. They may see something there that warrants extra caution. Or they may just look at all the comps - including Viola, Vasquez and guys who aren't typical comps like Kuroda and Sabathia - and have decided that Lester is too old to sign to a long-term deal.
 

WenZink

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DennyDoyle'sBoil said:
 
 I wouldn't have any problem with the Red Sox spending $30 million in each of the next two years for a top of the rotation starter.   They have it to spend in the next two years, can do so without luxury tax implications, and it's definitely a need unless we're all comfortable watching rookies and Doubront sixty percent of time, or more if Clay can't go every five days. ...
 
 
How about Cliff Lee?  He's due $25 mil in 2015, and has a $27.5 mil vesting option in 2016 (200 IP in 2015 or 400 IP in 2014-15).  The Phillies aren't going to give him away, but the more salary the Sox are willing to take on, the less they'll have to offer in trade.  Lee is old, in pitcher years, but in 2015, he'd still be a year younger than Schilling in his first year with the Sox.
 
If he starts succumbing to injuries in 2015, then the Sox can cut-and-run.
 

Apisith

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We would have to give prospects for Lee. He's earning his dough, a 5+ win pitcher year-in year-out isn't going to be given away for just cash, even if Amaro ends up deciding to want to cut payroll; there'll be other teams who can afford his contract and are willing to throw in prospects.
 

DennyDoyle'sBoil

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glennhoffmania said:
 
The AAV doesn't change so the luxury tax implications don't change. 
 
Ah, right.  This is the part I was forgetting.  Makes sense.
 

WenZink

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Apisith said:
We would have to give prospects for Lee. He's earning his dough, a 5+ win pitcher year-in year-out isn't going to be given away for just cash, even if Amaro ends up deciding to want to cut payroll; there'll be other teams who can afford his contract and are willing to throw in prospects.
 
I never suggested that Lee could be had for just cash.  But there are a limited number of teams that can take on Lee's salary, and the Sox appear to have the most payroll flexibility of any of the big revenue teams.  By mid-summer, the Sox might have a better idea about their Pawtucket rotation with Workman-De La Rosa-Webster-Ranaudo.  If the Sox opt to trade for Lee and let Lester walk, there's a comp pick in next year's draft, as well.
 

smastroyin

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It's interesting you guys mention Lee as an alternative to paying Lester.
 
The big thing about Cliff Lee is that he has steadily dropped his BB rate while maintaining his K rate which makes him look that much better when it comes to FIP and therefore WAR.
 
A single person does not predict the other, but couldn't Lee be added to the list as an example on the pro side of keeping Lester?  These careers are not quite as similar as they may look, so I don't really want to delve into the details completely, but look at the trending.
 
From Fangraphs.
 

 
 

WenZink

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smastroyin said:
It's interesting you guys mention Lee as an alternative to paying Lester.
....
 
I don't think it's "guys,"  I've just been running it up the flagpole every 5 days or so to see if anyone salutes.  I'm just trying to figure out what the Sox are going to spend their money on if they don't want to give our long-term contracts to a 30+ FA.  Cliff Lee for one year, with a vesting option for a 2nd seems to fit their thinking.  Then again, a 2015 rotation that has two 36 year olds(Lee/Lackey) at the top, could be asking for trouble.
 

The Gray Eagle

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So we're scared of paying Lester $20 million for his age 36 and 37 seasons, so to avoid that we're going to give up valuable prospects to pay Lee $27 million for his age 36 and 37 seasons? Or failing that, we'll probably have to sign some other veteran pitcher to a long term, big money deal. Who will probably be new to Boston and new to the AL East.
 
Giving Lester 6 years would be an "overpay" for a couple of years for sure, but it's extremely unlikely that you will be able to acquire a top of the rotation starter without overpaying. You have to assume that acquiring a vet pitcher with that kind of ability is going to involve overpaying in money, years, prospects-- or all of the above.
 
Some pitcher is probably going to be overpaid by the Red Sox soon. I'd rather we overpay players who have been a big part of multiple world championships with the Red Sox, who have shown they can excel in this environment, with Fenway as their home park, playing in the loaded AL East. Anyone who hasn't shown they can do that is going to have some additional risk beyond the standard age/injury/decline risks. And rewarding the players who have won titles for you sends a good message to the players in your system and also to potential free agents: the Red Sox value winning championships, and put their money where their mouth is. It's not just talk with them, if you bring home titles for them you will get rewarded. 
 
There are positions on the roster where you can try for value signings (LF, 1B, DH, closer, etc.) but I don't think top of the rotation starter is where you should look to go for value over quantity. If you want that kind of ability you're probably going to have to pay a ton to acquire it.
 
You should always be trying to develop those kind of pitchers, and we are, but that's always a crapshoot and we have no one like that ready to step in next year, which means if Lester walks then we will likely be trying to acquire someone like that. That is very expensive and risky. So it's not like letting Lester leave avoids risk and overpayment at all. It actually invites more of it, IMO.
 
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