Extending Lester

[DeJesus Built My Hotrod]

This idea of a hometown discount is a bit misleading.  
 
Lester is never going to accept something that the MLBPA will get upset about so why bother discussing it?  We are probably talking about the difference between six years and $150mm+ and six years and $135-140mm now.  
 
Note I am not talking about this spring when he was allegedly willing to sign for less.  That doesn't matter now and, if he was talking a deep enough discount (and mind you a discount for the Red Sox means years as well as - and maybe more than -  money) if there was a discount, it certainly wasn't enough to entice the Sox to get the deal done.

 

[tomdeplonty]

I asked the question trying get a sense whether the PA had real muscle in the negotiation, or whether this was more likely to be a face-saving excuse for no deal being made (an excuse that, as someone above pointed out, works nicely for both sides).

 

[DeJesus Built My Hotrod]

I asked the question trying get a sense whether the PA had real muscle in the negotiation, or whether this was more likely to be a face-saving excuse for no deal being made (an excuse that, as someone above pointed out, works nicely for both sides).

 
Oh I think you are on to something there as well.  The Sox can certainly leverage this as one of the reasons they failed to resign him.  
 
Based on the reports out there, it seems as if Lester would like to remain in Boston and would accept a decent discount versus what other teams would offer him, in order to do so.  Unfortunately, the delta between that number and what the Sox appear willing to pay seems to be pretty significant.   I would feel badly for him but he is likely to be paid so well this offseason that his grandchildren and perhaps great-grandkids will be set for life.

 

[Joshv02]

[QUOTE="Hriniak]
 
FA salaries set the benchmark for arbitration awards.
[/QUOTE]For third year arb players, but less significantly so for ayers below that. Then pre-fa contracts are given more weight.

 

[dcmissle]

No, it doesn't. And you can chalk much of A-Rod to Orza being a Yankee fan, which results in some awesome poetic justice.

 

[glennhoffmania]

They killed the Arod/Sox deal over a $12MM concession.
 
Gammons was just on WFAN and said he doesn't think the Sox will sign Lester, as Henry will not do a $140MM deal.

 
So does this mean if they trade for Stanton and he asks for an extension for 7/147 Henry will refuse?

 

[Bob Montgomerys Helmet Hat]

 
So does this mean if they trade for Stanton and he asks for an extension for 7/147 Henry will refuse?

Is Stanton a pitcher over 30?

 

[glennhoffmania]

I didn't hear the quote.  I was just going by what Bankshot posted.  It doesn't say anything about age or position.

 

[Bob Montgomerys Helmet Hat]

I didn't either.  So we don't know if it was a specific statement or a general statement.
 
So the answer to your question is that we have no idea.  And the answer to my question is no.

 

[glennhoffmania]

Well either way this is just stupid.  If they didn't sign Drew and AJP maybe he could afford to pay Lester what he's worth.

 

[bankshot1]

I didn't hear the quote.  I was just going by what Bankshot posted.  It doesn't say anything about age or position.

Gammons was speaking specifically of Lester.
 
But the question is interesting as in Henry's observation
“

To me,” Henry told 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. Yet teams continue to extravagantly overpay for players above the age of 30.”
 

 
he pegs the toxic  overpay age as 30, but does not address position.
 
If only Lester were a few months younger...

 

[DeJesus Built My Hotrod]

To be clear, I think John Henry et al would gladly pay Giancarlo Stanton a high dollar amount over seven years.  He is exactly the type of player they would indeed pay up for in both years and dollars.  He is not yet 25 and is just entering his prime.
 
The Henry quote is something that Posnanski and countless other observers of the sport have talked about.  Signing players over 30 to long-term contracts is a very risky proposition if the organization has to spend a significant portion of its annual budget servicing that one players contract.  
 
As a fan of a team that declines to play in this market, its frustrating because not only do you watch talented players go to teams willing to assume this risk but you are likely to lose quite a few homegrown stars too.  That said, there is something to be said for organizational discipline, especially if it gives you a chance to compete over the long haul rather than in small windows.  The Red Sox have been competitive for most of the time this ownership group has been in Boston and I will, at least, give them some benefit of the doubt even if it sucks to lose a guy like Lester.  And even if its to the free-spending rich kids to the south. 

 

[curly2]

 
This is where I am. In my experience, if your goal is to get a deal, the respose to 4/70 is 8/225. 

 
I think not doing this was smart for Lester and his agents. This way Lester is clearly the good guy in the talks. If Lester's camp had countered with a huge offer, the Sox certainly could have found a "friendly" reporter to leak that offer and paint Lester as greedy.

 

[Plympton91]

To be clear, I think John Henry et al would gladly pay Giancarlo Stanton a high dollar amount over seven years.  He is exactly the type of player they would indeed pay up for in both years and dollars.  He is not yet 25 and is just entering his prime.
 

That's nice, but the bidding for Stanton probably starts at 10 years.

At some point, you have to look at a 6 year, $132 million contract and say you're paying $35 million a year for the first three and hoping to get some residual value in thew last 3. For a team with a strong farm system, that should be feasible without hamstringing yourself. This team has 7, SEVEN pitching prospects in AAA and AA. If only 3 of them pan out, and only pan out as back of the rotation options, they are going to have ridiculously cheap starting pitching and middle relief optionsfor the next half decade. They could blow $22 million a season on Lester in years 4-6 and it's possible they'd still have a stronger team than they did last year while winning the world series.

 

[joe dokes]

That's nice, but the bidding for Stanton probably starts at 10 years.

At some point, you have to look at a 6 year, $132 million contract and say you're paying $35 million a year for the first three and hoping to get some residual value in thew last 3. For a team with a strong farm system, that should be feasible without hamstringing yourself. This team has 7, SEVEN pitching prospects in AAA and AA. If only 3 of them pan out, and only pan out as back of the rotation options, they are going to have ridiculously cheap starting pitching and middle relief optionsfor the next half decade. They could blow $22 million a season on Lester in years 4-6 and it's possible they'd still have a stronger team than they did last year while winning the world series.

 
I think what you're saying is accurate.  So, assuming the Sox aren't going to become a "let's pocket the money" group, I suppose their response would be that the way they expect/intend that they will spend that "blown" $66 million will have a greater benefit to the team than those 3 years of good Lester. That *has* to be their thinking, and as DeJesus said above, while frustrating,  there is something to be said for organizational discipline, especially if it gives you a chance to compete over the long haul rather than in small windows. The Red Sox have been competitive for most of the time this ownership group has been in Boston and I will, at least, give them some benefit of the doubt even if it sucks to lose a guy like Lester. And even if its to the free-spending rich kids to the south.

 

[lexrageorge]

 
They don't have authority but they can exert pressure.  I've heard this multiple times.  How exactly they do this, I don't know.  I think they were pretty unhappy with Pedroia's deal.

Technically, there is nothing the Players Association can do if Lester decides to take a below market deal to stay with the Red Sox.  As long as the contract abides by the CBA, Lester is free to sign it.  The issue with the A-Rod deal was that the Sox attempted to renegotiate the contract, and their terms were in violation of the CBA.  So the MLBPA said "no".  
 
My guess is that if Lester were to accept such a deal, he would not be in the running for any leadership position in the union.  I'm not sure how much of a consideration that is; Tony Gwynn didn't care at the time, and I'm not sure how much Pedroia cares now.  How much influence the PA has over Lester is an unknown. 
 
To restate the the obvious:  there is no moral, legal, or ethical obligation to the MLBPA that prevents Lester from accepting a below market deal.  However, there is also no similar obligation to accept such a deal from the Red Sox or any other team. 

 

[bankshot1]

To be clear, I think John Henry et al would gladly pay Giancarlo Stanton a high dollar amount over seven years.  He is exactly the type of player they would indeed pay up for in both years and dollars.  He is not yet 25 and is just entering his prime.
 
The Henry quote is something that Posnanski and countless other observers of the sport have talked about.  Signing players over 30 to long-term contracts is a very risky proposition if the organization has to spend a significant portion of its annual budget servicing that one players contract.  
 
As a fan of a team that declines to play in this market, its frustrating because not only do you watch talented players go to teams willing to assume this risk but you are likely to lose quite a few homegrown stars too.  That said, there is something to be said for organizational discipline, especially if it gives you a chance to compete over the long haul rather than in small windows.  The Red Sox have been competitive for most of the time this ownership group has been in Boston and I will, at least, give them some benefit of the doubt even if it sucks to lose a guy like Lester.  And even if its to the free-spending rich kids to the south. 

This is generally where I am. Sox ownership is smart, can assess risk, have been successful, deserve the benefit of the doubt, but they are not infallible.I think they've swapped one risk for another.
 
The over/under 30 line in the sand they' don't want to cross, while real, aging and injuries and performance are correlated, I hope the line in the sand is not carved in stone.
 
The question that I was really referring to,was not the signability of a 25 YO Stanton to a 7-year deal, but more whats the signability of a 29 YO pitcher to a 6 year deal vs a 30 YO pitcher to a 5 year deal etc. Do the Sox view the risks the same?  If the organizational philosophy is such that they abandon this end (high-end 30+) of the FA market, as already posted, the pressure to be smarter/luckier than everyone else in drafting and developing Stars/Aces grows to IMO unrealistic and sustainable levels. Sometimes you gotta say WTF, and take a risk. If ever the Sox were positioned to take a long-term financial risk, this seems to be the time.
 
And while I'm not xenophobic, (whatever) I would hate handing the MFY a Get out of jail free card. They appear to not have the prospects to trade for an Ace, but they have the money to bid for one. IMO losing Lester, a LHSP-Ace, critical to MFY success for as long as I can remember, is a 2X loss for the Sox.  And they would have to face him probably 4-5 times a year. But it is what it is.
 
I'm probably being unrealistic in my hopes that the Sox offer a realistic market-based deal to Lester, but to me it makes the most sense.
and it not my money.   

 

[rundugrun]

 
Lester said in an interview last week that there were multiple discussions after the 4/$70 offer was put on the table - 'moving the money and years around' but both sides being unable to come to an agreement at the time.

That's true, but here is the quote in the Globe article:

"Lester said that he never received another offer from the Red Sox beyond the reported initial offer of four years, seventy million..."

I'm sure there were talks and negotiations, but clearly the FO did not formally present an improved offer.

 

[Apisith]

The more that comes out, the more it looks like the FO monumentally fucked up. I mean, the consensus on SoSH, if I remember correctly, was 5/$100m. I thought that was expensive, and used the Beckett/Lackey contracts as a floor so went with 6/$110m. The way Lester is pitching this season, the first offer he gets in free agency will beat that.

If we don't sign him, we better have our eyes on someone else or the FO really have to believe that the young guys can step up.

 

[DeJesus Built My Hotrod]

The more that comes out, the more it looks like the FO monumentally fucked up. I mean, the consensus on SoSH, if I remember correctly, was 5/$100m. I thought that was expensive, and used the Beckett/Lackey contracts as a floor so went with 6/$110m. The way Lester is pitching this season, the first offer he gets in free agency will beat that.

If we don't sign him, we better have our eyes on someone else or the FO really have to believe that the young guys can step up.

No. The more that comes out, the more it looks like the FO was prepared to let Lester go. Six years, which seems to be his target contract length, is simply too long for the Sox.

Re: players over 30, the Sox aren't against signing them or paying market value as long as its not to a long term contract (> three or four years).

 

[Super Nomario]

No. The more that comes out, the more it looks like the FO was prepared to let Lester go. Six years, which seems to be his target contract length, is simply too long for the Sox.

Re: players over 30, the Sox aren't against signing them or paying market value as long as its not to a long term contract (> three or four years).

The length of the contract is part of compensation, though. If it's not a long-term contract, it's not market value. When was the last time a Lester-type signed a three- or four- year deal?

 

[glennhoffmania]

The length of the contract is part of compensation, though. If it's not a long-term contract, it's not market value. When was the last time a Lester-type signed a three- or four- year deal?

 
Lee took 5, even though I think he had 6 and 7 year offers from NY on the table at slightly lower AAVs.  But he was also older than Lester.  3 or 4 years?  Yeah I can't think of one.

 

[dcmissle]

A lot of things are debatable.

Not debatable is the fact that the RS cannot bend the market to their wishes. If they are out of the long term contract business for players at 30, they are out of the elite player business for players at that age -- unless they are blowing away AAV at a clip that would make no sense, which I doubt.

This is why the issue is bigger than Lester.

 

[bosockboy]

A lot of things are debatable.

Not debatable is the fact that the RS cannot bend the market to their wishes. If they are out of the long term contract business for players at 30, they are out of the elite player business for players at that age -- unless they are blowing away AAV at a clip that would make no sense, which I doubt.

This is why the issue is bigger than Lester.

Agreed.  While its not always advisable, it is sometimes necessary to remain competitive.  If they took this as a hard and fast rule they would almost solely be relying on the farm system and mid tier free agents to win.  They threaded the needle last year, but everything has to break perfectly.

 

[DeJesus Built My Hotrod]

The length of the contract is part of compensation, though. If it's not a long-term contract, it's not market value. When was the last time a Lester-type signed a three- or four- year deal?

Fair enough. To rephrase, it seems as if the Sox are willing to pay market value for the sub - premium over 30 FAs. That said, they don't seem inclined to play in the premium tier due to the length of contracts that market. I am sure there are exceptions but they are likely rare.

 

[bankshot1]

A lot of things are debatable.

Not debatable is the fact that the RS cannot bend the market to their wishes. If they are out of the long term contract business for players at 30, they are out of the elite player business for players at that age -- unless they are blowing away AAV at a clip that would make no sense, which I doubt.

This is why the issue is bigger than Lester.

Yes. That's the interesting question with long-term competitive ramifications. IMO the "never" rule on the high-end 30+ FA market creates some other risks.

 

[glennhoffmania]

I'd really like to know how they plan to fill out a ~$170m payroll with no elite players over 30.  I guess they can sign a bunch of Napoli/Dempster-type deals.  I keep saying that these guys are smarter than me so I have to defer to their judgment, but they ain't making it easy lately.

 

[mauf]

Agreed.  While its not always advisable, it is sometimes necessary to remain competitive.  If they took this as a hard and fast rule they would almost solely be relying on the farm system and mid tier free agents to win.  They threaded the needle last year, but everything has to break perfectly.

A big part of the value associated with club control of homegrown players is the ability, in many cases, to buy additional years of control at a discounted rate. So even if you took Henry's statement as a statement of unbending club policy on free-agent signings (and I don't think you should), the Sox could still have quality players signed well into their 30s.

 

[alwyn96]

That's true, but here is the quote in the Globe article:

"Lester said that he never received another offer from the Red Sox beyond the reported initial offer of four years, seventy million..."

I'm sure there were talks and negotiations, but clearly the FO did not formally present an improved offer.

 
It makes me really curious what counts as a 'formal offer' and what contract negotiations actually look like. If you can talk about moving years and money around, that sounds like negotiating to me. Is a 'formal' offer just a big stapled together stack of papers that's been notarized? I wonder if it costs a ton of money in fancy lawyerin' fees to put one together. It would seem like there isn't much point in putting a 'formal' offer out there if there wasn't some established verbal agreement beforehand. 
 
If Lester and the Red Sox are actually negotiating about years and money, then it seems like the 'no new formal offers' thing is kind of a red herring. 

 

[The Gray Eagle]

We'll all get the last laugh when Lester has a bad season for the Yankees in 2020. Ellsbury might be bad then too! They will have to pay luxury tax, and their payroll will be really high. I bet they will be sorry then. And we'll have several years of breaking in rookie pitchers before we get to celebrate that moment, and that always goes well in Boston. 
 
Lester's career, starting with his first full season:
2008: 210 IP, 144 ERA+
2009: 203 IP, 136 ERA+
2010: 208 IP, 134 ERA+
2011: 191 IP, 124 ERA+
2012: 205 IP, 87 ERA+
2013: 213 IP, 109 ERA+
2014: 137 IP, 155 ERA+ (on pace for about 220 IP)
 
He's averaged over 32 starts per season and in his career he has been on the DL for 2 weeks since he came back from cancer. His postseason record speaks for itself. 
 
I'm sure a rookie or two will step right in and replace that. Or maybe we can trade prospects for old Cliff Lee so we can pay him huge money for his age 36 and 37 seasons so we don't have to pay Lester for his age 35 and 36 seasons. Or maybe we can trade prospects for Cole Hamels, who hopefully can come over from the NL and do as well here, and then we can pay him till he's 35 so we don't have to pay Lester till he's 36. 
 
Sure, lowball Lester with an offer that he is guaranteed not to sign, and then never make him another offer. What could possibly go wrong? 

 

[StuckOnYouk]

Looking at all those IP makes me nervous.
Offer the man 3/100. You pay through the nose to get his 3 best years left and if he's confident in himself and wants to stay for the near term he can still land one more deal as a FA.
I mean if 3/90 would work that's better I'm just interested in what it would take to keep him for only next three years before he falls apart.

 

[Riggs]

We'll all get the last laugh when Lester has a bad season for the Yankees in 2020. Ellsbury might be bad then too! They will have to pay luxury tax, and their payroll will be really high. I bet they will be sorry then. And we'll have several years of breaking in rookie pitchers before we get to celebrate that moment, and that always goes well in Boston. 
 
Lester's career, starting with his first full season:
2008: 210 IP, 144 ERA+
2009: 203 IP, 136 ERA+
2010: 208 IP, 134 ERA+
2011: 191 IP, 124 ERA+
2012: 205 IP, 87 ERA+
2013: 213 IP, 109 ERA+
2014: 137 IP, 155 ERA+ (on pace for about 220 IP)
 
He's averaged over 32 starts per season and in his career he has been on the DL for 2 weeks since he came back from cancer. His postseason record speaks for itself. 
 
I'm sure a rookie or two will step right in and replace that. Or maybe we can trade prospects for old Cliff Lee so we can pay him huge money for his age 36 and 37 seasons so we don't have to pay Lester for his age 35 and 36 seasons. Or maybe we can trade prospects for Cole Hamels, who hopefully can come over from the NL and do as well here, and then we can pay him till he's 35 so we don't have to pay Lester till he's 36. 
 
Sure, lowball Lester with an offer that he is guaranteed not to sign, and then never make him another offer. What could possibly go wrong? 

This is perfect

 

[dcmissle]

This is perfect

Pretty much. I might have added Masterson in the Jose Offerman role, masquerading as the new ace.

 

[Doctor G]

If we really  have developed a great player development system, why should we allow the successful products of the system to leave when they  hit free agency.
 
The Red Sox  can't be the  best farm system the Yankees have. We get them to the majors go through the ups and downs of their early careers, and then let the Yankees sign them once they have proven themselves. 
 
ind of reminds me of the Kansas City  Athletics of the Fifties.
 
It is no victory to make the Yankees overspend. 

 

[gammoseditor]

We'll all get the last laugh when Lester has a bad season for the Yankees in 2020. Ellsbury might be bad then too! They will have to pay luxury tax, and their payroll will be really high. I bet they will be sorry then. And we'll have several years of breaking in rookie pitchers before we get to celebrate that moment, and that always goes well in Boston. 
 
Lester's career, starting with his first full season:
2008: 210 IP, 144 ERA+
2009: 203 IP, 136 ERA+
2010: 208 IP, 134 ERA+
2011: 191 IP, 124 ERA+
2012: 205 IP, 87 ERA+
2013: 213 IP, 109 ERA+
2014: 137 IP, 155 ERA+ (on pace for about 220 IP)
 
He's averaged over 32 starts per season and in his career he has been on the DL for 2 weeks since he came back from cancer. His postseason record speaks for itself. 
 
I'm sure a rookie or two will step right in and replace that. Or maybe we can trade prospects for old Cliff Lee so we can pay him huge money for his age 36 and 37 seasons so we don't have to pay Lester for his age 35 and 36 seasons. Or maybe we can trade prospects for Cole Hamels, who hopefully can come over from the NL and do as well here, and then we can pay him till he's 35 so we don't have to pay Lester till he's 36. 
 
Sure, lowball Lester with an offer that he is guaranteed not to sign, and then never make him another offer. What could possibly go wrong? 

 
I want Lester back, but it's pretty amazing to me that you can look at the data above and not understand why the Red Sox would be concerned prior to the start of the year (deleting the 155 ERA+ so far this year) giving Lester one of the largest contracts ever for a pitcher his age.  From 2012-2013 he was essentially league average, and stepped it up in the post-season.  Projections generally look at the 3 most recent years, weighing the most recent more.

 

[alwyn96]

We'll all get the last laugh when Lester has a bad season for the Yankees in 2020. Ellsbury might be bad then too! They will have to pay luxury tax, and their payroll will be really high. I bet they will be sorry then. And we'll have several years of breaking in rookie pitchers before we get to celebrate that moment, and that always goes well in Boston. 
 
Lester's career, starting with his first full season:
2008: 210 IP, 144 ERA+
2009: 203 IP, 136 ERA+
2010: 208 IP, 134 ERA+
2011: 191 IP, 124 ERA+
2012: 205 IP, 87 ERA+
2013: 213 IP, 109 ERA+
2014: 137 IP, 155 ERA+ (on pace for about 220 IP)
 
He's averaged over 32 starts per season and in his career he has been on the DL for 2 weeks since he came back from cancer. His postseason record speaks for itself. 
 
I'm sure a rookie or two will step right in and replace that. Or maybe we can trade prospects for old Cliff Lee so we can pay him huge money for his age 36 and 37 seasons so we don't have to pay Lester for his age 35 and 36 seasons. Or maybe we can trade prospects for Cole Hamels, who hopefully can come over from the NL and do as well here, and then we can pay him till he's 35 so we don't have to pay Lester till he's 36. 
 
Sure, lowball Lester with an offer that he is guaranteed not to sign, and then never make him another offer. What could possibly go wrong? 

 
Healthy pitchers get injured all the time. It's great that Lester has been durable, but I think there's an argument that past health for a pitcher isn't very predictive of future health, particularly as a pitcher gets older and older. 
 
I mean, I think obviously the concern is something like this:
 
age 23, 108 IP, 150ERA+
age 24,158 IP, 148ERA+
age 25, 228 IP, 182ERA+
age 26, 231 IP, 155ERA+
age 27, 233 IP, 162ERA+
age 28, 219 IP, 129ERA+
age 29, 234 IP, 166ERA+ (signed 6 year, $137M contract)
age 30, 166 IP, 130ERA+
age 31, 199 IP, 131ERA+
age 32, injured, did not play
age 33, 117 IP, 79 ERA+
age 34, injured, did not play
age 35, injured, did not play
 
I'm not saying that's what will happen, but better pitchers than Lester have fallen apart after 30, and I don't think one should just hand wave away the risk of that happening or get carried away with Lester's career year. Just as we shouldn't pretend that pitching prospects are sure things, we shouldn't pretend that the odds of a >30 year old pitcher living up to a mega-deal are very good. 
 
It would be harder to build a strong team without Lester, no doubt. I don't know where those wins would come from. But signing Lester is no guarantee of anything other than not having that money in the future.

 

[glennhoffmania]

 
I want Lester back, but it's pretty amazing to me that you can look at the data above and not understand why the Red Sox would be concerned prior to the start of the year (deleting the 155 ERA+ so far this year) giving Lester one of the largest contracts ever for a pitcher his age.  From 2012-2013 he was essentially league average, and stepped it up in the post-season.  Projections generally look at the 3 most recent years, weighing the most recent more.

 
First off, players are allowed to have a down year.  Looking at that list, which number sticks out at you?  2013 wasn't spectacular but it was pretty solid, and after a decent May and an awful June he was fantastic for the rest of the year.
 
Second, a dollar more than Bailey's deal wouldn't be one of the largest contracts ever for a pitcher his age.

 

[The Gray Eagle]

 
Healthy pitchers get injured all the time. It's great that Lester has been durable, but I think there's an argument that past health for a pitcher isn't very predictive of future health, particularly as a pitcher gets older and older. 
 
I mean, I think obviously the concern is something like this:
 
age 23, 108 IP, 150ERA+
age 24,158 IP, 148ERA+
age 25, 228 IP, 182ERA+
age 26, 231 IP, 155ERA+
age 27, 233 IP, 162ERA+
age 28, 219 IP, 129ERA+
age 29, 234 IP, 166ERA+ (signed 6 year, $137M contract)
age 30, 166 IP, 130ERA+
age 31, 199 IP, 131ERA+
age 32, injured, did not play
age 33, 117 IP, 79 ERA+
age 34, injured, did not play
age 35, injured, did not play
 
I'm not saying that's what will happen, but better pitchers than Lester have fallen apart after 30, and I don't think one should just hand wave away the risk of that happening. 

So we're going to sign a different pitcher who won't be risky and won't get hurt and won't decline? Who is less of a risk than Jon Lester and how do we get him? 
 
The Red Sox will have a veteran starting pitcher at the top of their rotation who will be relied on for 200+ innings every year. Maybe Lackey does that next year, if he doesn't hold out. Then who? How much will they have to pay that guy and how much risk will he have and how much talent will they have to give up to acquire him? Keep in mind this new pitcher will be stepping into the notorious Boston environment and have Fenway Park as his home park and the AL East as his primary opponents. 

 

[bankshot1]

I'm blaming Lester's 2012 on Valentine.
 
SOB
 
Its not like Lester is ancient or shopworn. He's 30 the same age of Hamels who the Sox are rumored to have scouted the past couple of weeks.
 
I wonder how much wishcasting the FO is doing that Henry Owens makes Sox fans forget Lester in '16.

 

[yecul]

The Sox made the mistake of making an opening offer bad enough to cease negotiations, but they did not know the Bailey comp going on. I understand their negotiation stance despite disagreeing with the approach. If you had told them back then that Bailey+$1 gets it done, then I imagine we would not be discussing this matter. Lester must not have told them that for some unknown reason.
 
This assumes we take that at face value, which seems dubious. I don't believe him.
 
In evaluating a pitcher I think track record and history obviously count for a lot, but you can't look at him in isolation. There is a lot of data to support the counter argument. That, despite his track record of quality and durability, he's a known quantity going forward. Pitchers fail all the time. The best data point to give hope in this thread was the overall workload compared to some of his peers (e.g. Sabathia has many more miles). His medicals are a major contributing factor to any projection going forward and we do not have those. 
 
As I've said before I do expect them to eventually sign him. If he sucks and/or is injured for 80% of the contract it wouldn't exactly be shocking. He's a pitcher. These things happen.

 

[tims4wins]

Looking at all those IP makes me nervous.
Offer the man 3/100. You pay through the nose to get his 3 best years left and if he's confident in himself and wants to stay for the near term he can still land one more deal as a FA.
I mean if 3/90 would work that's better I'm just interested in what it would take to keep him for only next three years before he falls apart.

 
Let's assume that Lester is going to receive 6/$150M from some team on the open market. If that is the case, then I'm not sure that 3 years and $100 is even enough. At 3/$100, Lester would then need to receive a 3/$50 deal at age 33 on the open market to equal the 6/$150. If he is healthy for the next 3 years, that seems like a reasonable deal. But if he happens to get hurt in the next 3 years, then that extra $50M is gone. Whereas if he signs a 6/$150 deal right now, he gets it all.
 
I think they'd have to pay even more of a premium for the first 3 years. I think I'd actually offer 4 years and $120M and see what he says.

 

[MuzzyField]

The time to re-extend Lester was following the 2012 season and lock him up until he's 34. This should be the plan to keep premium home grown talent. That didn't happen because Larry hired Bobby, Lester regressed, and the rest is history. Bobby V, the gift that keeps on giving.

I don't view Lester and Ellsbury as comparable. The Yanks are paying for the 2011 Dreamboat. A ship that has sailed and isn't coming back. Lester has produced at a pitching equivalent of Ellsbury 2011 with more frequency and has the obvious advantage of not having missed time due to injury.

I agree with the teams philosophy regarding players in their 30's. However, without access to the plan, I have concerns the Sox can both replace Lester, and add a premium bat while still having the prospects left to successfully supplement their own roster needs.

If Lester really wants to stay, he realistically is looking at a higher AAV offer for 4 years maybe 5. Stay healthy and he can enjoy the Papi treatment and retire with the Sox, if not, the team isn't on the hook for an extended performance/injury risk they view as likely to occur.

 

[alwyn96]

So we're going to sign a different pitcher who won't be risky and won't get hurt and won't decline? Who is less of a risk than Jon Lester and how do we get him? 
 
The Red Sox will have a veteran starting pitcher at the top of their rotation who will be relied on for 200+ innings every year. Maybe Lackey does that next year, if he doesn't hold out. Then who? How much will they have to pay that guy and how much risk will he have and how much talent will they have to give up to acquire him? Keep in mind this new pitcher will be stepping into the notorious Boston environment and have Fenway Park as his home park and the AL East as his primary opponents. 

 
I don't know who is going to be the #1 starter in 2016. Even if the Red Sox resign him, it may not be Lester, anyway. Maybe they sign Shields or something or make a deal for a guy. I'm sure they'll figure something out. They have some time on that one. 
 
I'm not saying I'm against resigning Lester, but I'm not going to pretend that over 30 pitchers are anything like sure things. Signing guys at any cost can really come back to bite you. Just looking at a pitcher's stats and assuming they're going to be the same going forward is a recipe for heartbreak. 

 

[glennhoffmania]

 
Let's assume that Lester is going to receive 6/$150M from some team on the open market. If that is the case, then I'm not sure that 3 years and $100 is even enough. At 3/$100, Lester would then need to receive a 3/$50 deal at age 33 on the open market to equal the 6/$150. If he is healthy for the next 3 years, that seems like a reasonable deal. But if he happens to get hurt in the next 3 years, then that extra $50M is gone. Whereas if he signs a 6/$150 deal right now, he gets it all.
 
I think they'd have to pay even more of a premium for the first 3 years. I think I'd actually offer 4 years and $120M and see what he says.

 
If you could get him for 6/140, that makes way more sense then 4/120.  The odds of him not being worth 20m in years 5 and 6 are slim.  Plus you reduce the AAV from 30 to 23.

 

[maxotaur]

Looking at all those IP makes me nervous.
Offer the man 3/100. You pay through the nose to get his 3 best years left and if he's confident in himself and wants to stay for the near term he can still land one more deal as a FA.
I mean if 3/90 would work that's better I'm just interested in what it would take to keep him for only next three years before he falls apart.

Or you could look at that list and think "Hey, he's a durable pitcher".

Ex's - Clemens, Pedro, Schilling, Ryan, Petite, Lackey, Seaver, Arroyo, Hernandez,Scott, Hunter, Palmer, Blue, Verlander, Guidry, Maddox, Smoltz, Johnson, Carlton, Glavine, Carlton, Gibson, Carpenter, Mussina, Hershiser, Blyleven, Sutton, Perry, Koosman, Tanana,
Feller, Morris, Rodgers, Tiant, Cone, Burnett, Haren, Leiter, Guidry, Cain, Park, Hamels, Shields, Greinke, Lincecum, Weaver...

That's just to name a few. Lester's been on the DL 2 weeks in his career. What makes you think that would change?

 

[tims4wins]

 
If you could get him for 6/140, that makes way more sense then 4/120.  The odds of him not being worth 20m in years 5 and 6 are slim.  Plus you reduce the AAV from 30 to 23.

 
Isn't everyone concerned that the opposite is true - that there is little chance he will be worth $20M at ages 35-36?

 

[glennhoffmania]

 
Isn't everyone concerned that the opposite is true - that there is little chance he will be worth $20M at ages 35-36?

 
If he has a career ending or altering injury, sure.  If he's able to pitch I think it's reasonable to assume that he'll be worth $10m per year in 5 years.  Plus there's the benefit of a lower AAV.

 

[judyb]

Isn't everyone concerned that the opposite is true - that there is little chance he will be worth $20M at ages 35-36?

If you're already betting on him being worth $30M a year for the first 4 years, you might as well bet on him being worth $10M a year for the next 2. There's obviously a point where paying more per year for fewer years goes from being avoiding too long a commitment to just paying more to get less, and that might be it.

 

[uncannymanny]

The time to re-extend Lester was following the 2012 season and lock him up until he's 34. This should be the plan to keep premium home grown talent. That didn't happen because Larry hired Bobby, Lester regressed, and the rest is history. Bobby V, the gift that keeps on giving.

I don't view Lester and Ellsbury as comparable. The Yanks are paying for the 2011 Dreamboat. A ship that has sailed and isn't coming back. Lester has produced at a pitching equivalent of Ellsbury 2011 with more frequency and has the obvious advantage of not having missed time due to injury.

I agree with the teams philosophy regarding players in their 30's. However, without access to the plan, I have concerns the Sox can both replace Lester, and add a premium bat while still having the prospects left to successfully supplement their own roster needs.

If Lester really wants to stay, he realistically is looking at a higher AAV offer for 4 years maybe 5. Stay healthy and he can enjoy the Papi treatment and retire with the Sox, if not, the team isn't on the hook for an extended performance/injury risk they view as likely to occur.

 
What would compel Jon Lester to sign such a deal?

 

[bankshot1]

 
Isn't everyone concerned that the opposite is true - that there is little chance he will be worth $20M at ages 35-36?

That should be the expectation.With free-agency you may have to buy 6 to get 4.
 
I think going in, the assumption is you get may get 4 years of top of the rotation years (1-2) then 2 years of middle/end (3-4-5) of rotation years.
 
And as Lester moves through the pitcher's life-cycle, RDLR, Owens, Workman or the ProspectTBNL  mature and move-up in the rotation. But these guys are pitching on rookie pre-arb salaries. 
 
Or maybe Lester flames out next year.
 
or wins the CY
 
There are no guarantees.