Extending Lester

[Snodgrass'Muff]

 
I think it would be highly out of character for the front office to sign a 30+ year old starting pitcher to a 6+ year deal. And Lester probably has his agent whispering in his ear that he could make $175 million if he reaches free agency. Statistically, players don't return when they reach free agency. It would seem like a waste to give up the chance of acquiring a top 50 prospect and opening up a rotation spot for a minor league player to audition because there's something like a 5% chance that Lester would re-sign with us after reaching free agency.

 
Again, your guess at the odds is ridiculously low.  He's said he wants to stay.  This isn't the Ellsbury situation playing out again.  I'd say their odds of getting an extension done are probably at least 50% right now.  If they don't get it done before the season ends, that number drops, but not to 5%.

 

[Hoplite]

 
Again, your guess at the odds is ridiculously low.  He's said he wants to stay.  This isn't the Ellsbury situation playing out again.  I'd say their odds of getting an extension done are probably at least 50% right now.  If they don't get it done before the season ends, that number drops, but not to 5%.

 
Agree the disagree on the percentages I guess. In the scenario where Lester does re-sign, do you expect the Red Sox to double their original offer to $150+ million or do you expect Lester to take a significant discount from what he's likely being told that he could make in free agency? That's the part I have a hard time envisioning.
 
I can't find the article now, but does anyone remember an article from this year that gave the statistic on the amount of big name free agents who actually re-sign with their previous team once they reach free agency? I remember it being virtually non-existent.

 

[Snodgrass'Muff]

I'd guess a deal gets done in the 6/140 range.  Lester's camp floated 5/120 as a number that gets them back to the table.  So 6/140 or maybe 6/150 is a reasonable step up from that and if his desire to stay in Boston is genuine, it should get the job done.
 
My biggest problem with your position is that you are starting from the assumption that he's already a lock to hit free agency.  They have a half a season's worth of an exclusive negotiating window.  So how often players re-sign with their teams once they hit the market isn't all that relevant yet.

 

[Bob Montgomerys Helmet Hat]

 
There are so few $150Million dollar contracts for pitchers. Hernandez, Verlander, Sabathia, Kershaw, Tanaka, I think. Sabathia's obviously ended up too long after the opt-out. The others are probably too early to tell, but I'd be happy if the Red Sox had most of them.
 
But there are lots of great players who are 30+.  Are the Red Sox really never going to sign an elite player into their 30's?  Is all their cash going into Victorino-type contracts and Dempster-type contracts and Peavy pick-ups? Are those clearly better deals?

I guess I'm not stuck on the $150 million number for the comp.  I'm talking about long term contracts at the very high end for pitchers even approaching 30.  Zito, Santana.  Hampton, etc.  It's just a very risky proposition, based on history.
Maybe the Sox are going to focus more on Cuban players, but really,  I have no idea what their plan is.  But I'm confident they have a plan, and if it doesn't include signing very high end, long term contracts to pitchers heading into their 30's, I can live with that as a strategy.

 

[Hoplite]

I'd guess a deal gets done in the 6/140 range.  Lester's camp floated 5/120 as a number that gets them back to the table.  So 6/140 or maybe 6/150 is a reasonable step up from that and if his desire to stay in Boston is genuine, it should get the job done.
 
My biggest problem with your position is that you are starting from the assumption that he's already a lock to hit free agency.  They have a half a season's worth of an exclusive negotiating window.  So how often players re-sign with their teams once they hit the market isn't all that relevant yet.

 
I didn't start from the assumption that he was a lock to hit free agency, I was probably 75% sure the Red Sox and Lester would agree on an extension before the season began. But I also thought the Red Sox would be competitive this year and that Lester wouldn't be having the best year of his career at age 30. It hasn't been the front office's style to sign players when their value are at an all-time high and will likely only decrease. Cherington and Co. seem like a rather calculated and analytic group of people and I doubt half a good year will cause them to double their evaluations of what Lester is worth. Unless ownership steps in, which I'm not sure would be good, I don't think we re-sign Lester. And given how far apart the front office and Lester were last we knew, I don't think it's a matter of just needing two more months to find common ground.
 
Even if I thought there was a 50/50 chance that we re-sign Lester, I think I'd still be on the fence of re-signing Lester to a $150+ million contract for his age 31+ seasons versus acquiring a top 50 prospect for him.

 

[Snodgrass'Muff]

 
I didn't start from the assumption that he was a lock to hit free agency, I was probably 75% sure the Red Sox and Lester would agree on an extension before the season began. But I also thought the Red Sox would be competitive this year and that Lester wouldn't be having the best year of his career at age 30. It hasn't been the front office's style to sign players when their value are at an all-time high and will likely only decrease. Cherington and Co. seem like a rather calculated and analytic group of people and I doubt half a good year will cause them to double their evaluations of what Lester is worth. Unless ownership steps in, which I'm not sure would be good, I don't think we re-sign Lester. And given how far apart the front office and Lester were last we knew, I don't think it's a matter of just needing two more months to find common ground.
 
Even if I thought there was a 50/50 chance that we re-sign Lester, I think I'd still be on the fence of re-signing Lester to a $150+ million contract for his age 31+ seasons versus acquiring a top 50 prospect for him.

 
PP covered part of this, the other part I'll address.  I said "are starting from" as in present tense, as in right now you are posting as though you believe he's now a lock to hit free agency.  He's a long way from that and throwing numbers around that ignore the fact that the team still has 4 months to try and come to an agreement isn't terribly productive.  Sure, he may hit free agency.  And sure, if he does, the chances of him coming back go way down.  He's not there yet, though and recent reports suggest the two sides are still talking and that Lester is hoping to be in Boston for his next contract.
 

Players, especially upper echelon ones, who hit free agency don't generally resign with their old teams (unless they're Yankees). In order for that to happen, the Sox have to value Lester higher than any other team, how likely is that to happen? If they are going to bring him back, they need a deal within the next week or two.

 
Why do they have to value him more highly than any other team?  If Lester's desire is to stay in Boston, isn't it the other teams that will have to value him higher to lure him away?  Hell, other teams will have to significantly overvalue him once you add the QO to the equation.  The deck is stacked in Cherington's favor.  That doesn't mean Lester is a lock to come back, but the defeatist attitude some posters have about this situation is kind of baffling.
 
I also don't see why they have to sign him in the next couple of weeks.  If they have the framework of a deal worked out by then, allowing talks to linger into the late summer would be just fine.  I still think the chances of him being dealt by the trade deadline are very slim.  The team would need to be really sure that they're not going to come to terms and that they'd rather have whatever the return is than the draft pick, slot value and what they'd be depriving the signing team of for luring him away.  None of that is anywhere near a given.

 

[dcmissle]

Let's ignore the numerous elephants in the room -- the Crawford contract, the AGon contract and others -- and assume that Ben and Co wiped the slate clean and are calling the shot here.

They can be as calculating and analytic as they please, but one approach does not fit all situations. There is no hard cap at work here, and the financial risk runs in both directions, and by that I mean the revenue side too.

The worst case is not Lester failing to live up to a fair market value contract. It's him living up to such a contract in NY, for example, while the Red Sox fail to fill the void here.

There are no guarantees either way, obviously, But the conservative play is to make the investment, unless the market for Lester gets entirely out if hand, in which case you will have done your best and everyone will know it.

 

[Hoplite]

 
We don't know what they offered or how far apart they were. We have rumors about 4/$70 with no substantiation. We have no word one way or another if that was an opening bid, if there was any counter offer from Lester's side or if the Sox followed up with something after that.
 
And even if we did, what they offered is not necessarily what they think he is worth. 

 
Lucchino himself acknowledged the 4/$70 million offer. There have since been conflicting reports about whether Lester would consider renegotiating, but there have been multiple reports stating that there has been no meaningful progress, and that extension talks are "all but over". Sentimentally, I love Lester. But realistically, it doesn't sound like an extension is likely, nor is it likely that we'd outbid 29 other teams for his services in free agency or that he'd take a significant pay cut to stay here once he does reach free agency.

 

[dcmissle]

Seems right, and what follows --

1. Don't expect a ton for him in a trade, barring somebody going down on a legit contender very soon, (Not a lot of Oakland As in the mix)

2. The value scenario of trade him and then sign him as a FA is a mirage. How often does THAT happen?

 

[BosRedSox5]

It's not defeatist, it's acknowledging historical precedent. When players become free agents, they entertain offers and usually sign with the highest bidder (such as how the Sox landed Crawford, Lackey, Manny, etc) and the existing team is usually not the high bidder (exception being the Yankees who are never outbid).

Do you have examples of players like Lester who resigned with their current team? It just doesn't happen.

It doesn't happen because if a player reaches free agency either their original team can't afford them or doesn't value them highly enough to lock them down at market rates before the season's over.

The way you put it is really player centric. It seems to me that their club is the biggest catalyst in the decision to test free agency.

 

[Snodgrass'Muff]

 
Lucchino himself acknowledged the 4/$70 million offer. There have since been conflicting reports about whether Lester would consider renegotiating, but there have been multiple reports stating that there has been no meaningful progress, and that extension talks are "all but over". Sentimentally, I love Lester. But realistically, it doesn't sound like an extension is likely, nor is it likely that we'd outbid 29 other teams for his services in free agency or that he'd take a significant pay cut to stay here once he does reach free agency.

 
And here's a post from 2 days later citing an article that says an extension in season is still a possibility and that Lester's camp would come back to the table if the Sox opened a new round of discussions at 5/120 or so.  This was less than a page ago and was referenced again a few posts ago.  The talks are not all but dead.  They will continue negotiating until they reach a deal or the season ends.
 

It's not defeatist, it's acknowledging historical precedent. When players become free agents, they entertain offers and usually sign with the highest bidder (such as how the Sox landed Crawford, Lackey, Manny, etc) and the existing team is usually not the high bidder (exception being the Yankees who are never outbid).

Do you have examples of players like Lester who resigned with their current team? It just doesn't happen.

 
Again, he's not a free agent yet.  That's why your position is defeatist.  You're looking ahead with the assumption that an extension won't happen.  It very well still might.

 

[Hoplite]

 
And here's a post from 2 days later citing an article that says an extension in season is still a possibility and that Lester's camp would come back to the table if the Sox opened a new round of discussions at 5/120 or so.  This was less than a page ago and was referenced again a few posts ago.  The talks are not all but dead.  They will continue negotiating until they reach a deal or the season ends.
 
 
Again, he's not a free agent yet.  That's why your position is defeatist.  You're looking ahead with the assumption that an extension won't happen.  It very well still might.

 
I assume you meant to link to this article - http://fullcount.weei.com/sports/boston/baseball/red-sox/2014/07/04/sources-jon-lester-would-listen-during-season-if-red-sox-offer-led-to-short-negotiations/
 

It is believed that an offer in the vicinity of five years, $120 million — which would be somewhat in line with what Philadelphia’s Cole Hamels signed for when inking his six-year, $144 million (with a $20 million club option for 2019) — would be in the neighborhood of what might lead Lester to giving the go-ahead for talks to resume.
 

 
That's all it said. There were no indications that the Red Sox would indeed make an offer like that, nor was it definitive that Lester would listen if they did.

 

[HriniakPosterChild]

Do you have examples of players like Lester who resigned with their current team? It just doesn't happen.

 
Bret Boone with the M's.
 
Man, that one ended badly.

 

[Snodgrass'Muff]

 
I assume you meant to link to this article - http://fullcount.weei.com/sports/boston/baseball/red-sox/2014/07/04/sources-jon-lester-would-listen-during-season-if-red-sox-offer-led-to-short-negotiations/
 
 
That's all it said. There were no indications that the Red Sox would indeed make an offer like that, nor was it definitive that Lester would listen if they did.

 
No, I meant to link to the post to show you how recently that was mentioned in this very thread.  If Lester is still interested in working out an extension, then why are you assuming he's going to hit the free agent market?  If the front office isn't interested, even at 5/120, what is the point of throwing out percentages for how likely you think it is that he'll end up re-signing?  If they don't want him back, the chances he re-signs are 0%.  If they are interested in working out a deal, the fact that Lester's camp said talks aren't dead and that a reasonable offer would get them headed toward a deal trumps your estimates.
 
Your position lacks evidence and consistency.  What we know is that Lester's camp wants to work out a deal and that they aren't starting from an unreasonable number.  We also know that the Red Sox are interested in extending Lester, though we don't know exactly what their limit is.
 
From that you are leaping to the conclusion that Lester is going to hit the free agent market and that he's essentially gone once that happens.  It's a bizarre position to take.

 

[Hoplite]

 
No, I meant to link to the post to show you how recently that was mentioned in this very thread.  If Lester is still interested in working out an extension, then why are you assuming he's going to hit the free agent market?  If the front office isn't interested, even at 5/120, what is the point of throwing out percentages for how likely you think it is that he'll end up re-signing?  If they don't want him back, the chances he re-signs are 0%.  If they are interested in working out a deal, the fact that Lester's camp said talks aren't dead and that a reasonable offer would get them headed toward a deal trumps your estimates.
 
Your position lacks evidence and consistency.  What we know is that Lester's camp wants to work out a deal and that they aren't starting from an unreasonable number.  We also know that the Red Sox are interested in extending Lester, though we don't know exactly what their limit is.
 
From that you are leaping to the conclusion that Lester is going to hit the free agent market and that he's essentially gone once that happens.  It's a bizarre position to take.

 
We don't know that Lester's camp is interested in an extension. It was suggested that a $120 million offer "might" bring him back to the table. Nor has there been any indication that the Red Sox would be interested in making the hypothetical offer that might bring him back to the negotiating table. Nor has the existing front office shown a willingness to sign these types of contracts. I'm not saying that they never will, but it's something to consider. Me giving a percentage likelihood that I think we'll retain Lester really isn't much different than you saying it's 50/50. I don't feel the need to tell you your percentage is wrong though or characterize it as "bizarre" just because I disagree with it. The truth is we don't truly know what Lester or the Sox are thinking and we're both speculating.

 

[Yelling At Clouds]

It's not defeatist, it's acknowledging historical precedent. When players become free agents, they entertain offers and usually sign with the highest bidder (such as how the Sox landed Crawford, Lackey, Manny, etc) and the existing team is usually not the high bidder (exception being the Yankees who are never outbid).

Do you have examples of players like Lester who resigned with their current team? It just doesn't happen.

 
Anibal Sanchez, Matt Holliday

 

[Hoplite]

The main reason big name free agents almost never re-sign with their previous team when they make it to free agency is probably because if they're willing to take a discount to stay somewhere, they almost always work out an extension. So Boone and Lee probably aren't good examples. I believe Lowell made it to free agency before re-signing with us at a discount during the 2007/2008 offseason. It might be a stretch to say he was a "big name" free agent though. I'm sure there have been more, but what he did was the exception to the rule.

 

[Snodgrass'Muff]

 
We don't know that Lester's camp is interested in an extension. It was suggested that a $120 million offer "might" bring him back to the table. Nor has there been any indication that the Red Sox would be interested in making the hypothetical offer that might bring him back to the negotiating table. Nor has the existing front office shown a willingness to sign these types of contracts. I'm not saying that they never will, but it's something to consider. Me giving a percentage likelihood that I think we'll retain Lester really isn't much different than you saying it's 50/50. I don't feel the need to tell you your percentage is wrong though or characterize it as "bizarre" just because I disagree with it. The truth is we don't truly know what Lester or the Sox are thinking and we're both speculating.

 
The difference between our positions is mine is based on what Lester's camp and the Red Sox have actually said.  Yours is based on the assumption that what they've said is not true and that either Lester's desire is to test the waters in free agency or that the Red Sox aren't willing to pay a reasonable rate to retain his services.
 
Both sides have said they want to get a deal done.  Neither side has said anything to support the belief that talks are all but dead or that they are too far apart for us to hope that they get an extension worked out.
 
If you can provide something from either camp (or preferably both) to support the claim that there is only a 10% chance he re-signs with Boston, I'd love to see it.  Until then, your position is baseless as far as I can tell.

 

[Plympton91]

 
We don't know what they offered or how far apart they were. We have rumors about 4/$70 with no substantiation. We have no word one way or another if that was an opening bid, if there was any counter offer from Lester's side or if the Sox followed up with something after that.
 
And even if we did, what they offered is not necessarily what they think he is worth. 

What exactly would you call "substantiation?" We have an uncorrected and unrefuted report of Peavy saying, "Maybe now they'll offer him $80 million." I'd call that pretty clear evidence that the 4 year $70 million offer is a legitimate report. They blew it. Maybe hindsight will prove them right, as nobody knows whether John Lester or Ruby De La Rosa or Henry Owens will be healthy next July, but ex ante, they blew it.

 

[MakMan44]

What exactly would you call "substantiation?" We have an uncorrected and unrefuted report of Peavy saying, "Maybe now they'll offer him $80 million." I'd call that pretty clear evidence that the 4 year $70 million offer is a legitimate report. 

What? You have no idea if that's true. That could also be Peavy making a joke about the reports. 

 

[Hoplite]

 
The difference between our positions is mine is based on what Lester's camp and the Red Sox have actually said.  Yours is based on the assumption that what they've said is not true and that either Lester's desire is to test the waters in free agency or that the Red Sox aren't willing to pay a reasonable rate to retain his services.
 
Both sides have said they want to get a deal done.  Neither side has said anything to support the belief that talks are all but dead or that they are too far apart for us to hope that they get an extension worked out.
 
If you can provide something from either camp (or preferably both) to support the claim that there is only a 10% chance he re-signs with Boston, I'd love to see it.  Until then, your position is baseless as far as I can tell.

 
No, that's factually untrue. Your position is based off what Rob Bradford said "industry sources" suggested "might" bring Lester back to the table. What Lester's camp has actually said recently is:
 
July 4th - http://www.cbssports.com/mlb/writer/jon-heyman/24607797/ace-lefty-lester-tells-red-sox-to-halt-contract-talks-until-after-season
 
 

Red Sox ace Jon Lester has told the team he would prefer to concentrate on his pitching and the season, so both parties are now operating on the assumption there's a good chance that contract talks are off until season's end.
 

 
June 30th - http://fullcount.weei.com/sports/boston/baseball/red-sox/2014/06/30/jon-lester-contract-talks-a-distraction-we-dont-need/
 

 
 
NEW YORK — Red Sox left-handerJon Lester said that reports that contract talks between him and the team have resumed are off the mark. The 30-year-old, who will be eligible for free agency after the season, said that he is not talking with the team about contract terms, and further said that he does not plan to do so during the season.

 
You can't provide anything definitive that says chances are 50/50 just like I can't provide anything definitive that chances are 10%. That doesn't make your opinion baseless or bizarre or whatever else. It just means we disagree about how to interpret what's been reported.

 

[Snodgrass'Muff]

 
No, that's factually untrue. Your position is based off what Rob Bradford said "industry sources" suggested "might" bring Lester back to the table. What Lester's camp has actually said recently is:
 
July 4th - http://www.cbssports.com/mlb/writer/jon-heyman/24607797/ace-lefty-lester-tells-red-sox-to-halt-contract-talks-until-after-season
 
 
 
June 30th - http://fullcount.weei.com/sports/boston/baseball/red-sox/2014/06/30/jon-lester-contract-talks-a-distraction-we-dont-need/
 
 
You can't provide anything definitive that says chances are 50/50 just like I can't provide anything definitive that chances are 10%. That doesn't make your opinion baseless or bizarre or whatever else. It just means we disagree about how to interpret what's been reported.

 
The July 4th article you are citing as evidence that Lester is 90% likely to be gone also says...
 

One person close to Lester said he believes Lester has a desire to continue with the Red Sox, though of course as a free agent, there will be plenty of suitors. That person said he'd still be "surprised" if Lester didn't end up back in Boston.

 
The June 30th article says...
 

That said, Lester said that his preference to hold off on talks until after the season in no way should be interpreted as a diminished desire to remain with the Sox.

 
Sounds like a guy who wants to stay in Boston and not someone who is 90% likely to leave.  Even the articles you cite as evidence disagree with your take.  But whatever.  If you want to sweat this situation unnecessarily, it's no skin off my back.

 

[Yelling At Clouds]

Sanchez and Holliday are fair examples, but also players who had been with their teams for just a year prior to resigning. Holliday's AAV didn't even increase when he resigned.
 

 
Paul Konerko, then.

 

[HriniakPosterChild]

Sounds like a guy who wants to stay in Boston and not someone who is 90% likely to leave.  Even the articles you cite as evidence disagree with your take.  But whatever.  If you want to sweat this situation unnecessarily, it's no skin off my back.

 
Or it could be a nice thing to say that has the side-effect of driving up the NY/Cubs/Whoevers offers after he hits free agency.

 

[Hoplite]

 
The July 4th article you are citing as evidence that Lester is 90% likely to be gone also says...
 
 
 
 
The June 30th article says...
 
 
 
 
Sounds like a guy who wants to stay in Boston and not someone who is 90% likely to leave.  Even the articles you cite as evidence disagree with your take.  But whatever.  If you want to sweat this situation unnecessarily, it's no skin off my back.

 
Of course Lester's going to stay he wants to stay here, that's what impending free agents always say. I wouldn't be surprised if he was being genuine, but he's still going to want to get paid. Lester himself goes on at length in the June 30th article about why he doesn't want to re-open negotiations during the season. I'm not sure how he could have been much more clear...
 

 
“I think it’s an added distraction that we don’t need right now,” said Lester. “We need to focus on playing good baseball and getting back to the top of the East and going from there, hopefully getting to the playoffs. We don’t need to be worried about my contract stuff. That’s the last thing I want these guys to have to answer questions about. I mean, kind of like tonight — we got a big win, took a series from the Yankees, playing good baseball and we’re sitting here talking about this. This is the last thing we need to be talking about right now.
“I don’t think they’ve started anything,” Lester added of the idea that he was engaged in renewed contract talks. “I know the conversation has been there throughout the season, different topics. Like I said from the beginning of the season, everything is amicable. Conversations continue. But nothing as far as contract or numbers or anything like that.”
Asked if the Red Sox had reached out to his representatives about in-season talks, Lester responded, “No, not that I’m aware of.”

 

 
“Like I’ve kind of been pretty consistent with, you’re just asking for trouble when you do something like [talk about a contract in-season],” he said. “For me, our focus, my focus right now is getting this team back to where it needs to be. With that being said, the last thing I want is these guys having to answer questions about me. Like I’ve said, per Red Sox protocol, we’ll just put it off to the end and talk then when it’s more appropriate, hopefully after another World Series. I just think right now is not too good of a time.
“My focus has been [pitching],” he said. “It’s not just a distraction for me. It’s a distraction for everybody. … Coming in, take two out of three, and we’ve got to answer questions about this. We’re not talking about the right things. I just feel like the less guys can talk about that sort of thing, the better. We’ll figure stuff out as we go.”

 
And that might not be a bad thing. I'm not sweating Lester not re-signing because I'm not convinced re-signing him on the contract he'd probably want would be worth it.

 

[Hoplite]

 
 
Or it could be a nice thing to say that has the side-effect of driving up the NY/Cubs/Whoevers offers after he hits free agency.
 

 
Exactly. Out of curiosity, when was the last time a big name free agent said that they did not want to re-sign with their current big market team?

 

[Bob Montgomerys Helmet Hat]

 
Exactly. Out of curiosity, when was the last time a big name free agent said that they did not want to re-sign with their current big market team?

Papelbon?  Ellsbury?

 

[Hoplite]

Papelbon?  Ellsbury?

 
Really, as free agents they explicitly said that they did not want to re-sign with Boston?

 

[Bob Montgomerys Helmet Hat]

 
Really, as free agents they explicitly said that they did not want to re-sign with Boston?

Of course not.  Not even the stupidest(Papelbon) would do that.
 
EDIT--I don't, however, remember Papelbon ever saying that he did want to re-sign with Boston, but that's not the same thing.  All he kept talking about was testing the market.

 

[Hoplite]

Of course not.  Not even the stupidest(Papelbon) would do that.
 
EDIT--I don't, however, remember Papelbon ever saying that he did want to re-sign with Boston, but that's not the same thing.  All he kept talking about was testing the market.

 
Hence the question, when was the last time a big name free agent stated that they did not want to re-sign with a big market team they left as a free agent? I'm sure someone was dumb and angry enough to do it at some point.

 

[Rasputin]

I'd say there's about a 10% chance that we re-sign Lester at this point and maybe a 5% chance that we sign someone more expensive like Scherzer. Unless this team turns things around within the next two weeks, I imagine we'll trade Lester and call up Webster, Ranaudo and De La Rosa in the hopes that one of them performs well enough to earn a rotation spot in 2015.

 
Stuff like this drives me nuts. You're basing your ten percent on what, that a deal hasn't happened yet?
 
We know Lester wants to stay here. We know the Red Sox want him to stay here. That's got to add up to more than ten percent.

 

[Hoplite]

 
Stuff like this drives me nuts. You're basing your ten percent on what, that a deal hasn't happened yet?
 
We know Lester wants to stay here. We know the Red Sox want him to stay here. That's got to add up to more than ten percent.

 
It drives me nuts when someone tells me that under no circumstances will the Red Sox re-sign Drew because they've been watching baseball for a long time and they truly understand the front office. To each their own.

 

[MuzzyField]

I'm in the camp of getting something done over the break only because there's no reason not to. The value of Lester is greater than the Sox reported opening offer. How high does the team want to go? How low is Lester winning to go? Figure it out and move on with an extension or a trade. The benefits of sucking are few, but one is being able to move forward. The moves made can be better executed knowing if the best pitcher on the team is going to be there or not. The Red Sox have the money to pay reasonable market value, not Ellsbury money. If reasonable market value is enough or not, let's check off the Lester box yes or no and move forward and tackle a pretty extensive to-do list for 2015.

 

[Rasputin]

It drives me nuts when someone tells me that under no circumstances will the Red Sox re-sign Drew because they've been watching baseball for a long time and they truly understand the front office. To each their own.

You're neglecting the fact that I was right. Despite the poor defensive play by Bogaerts, Drew want signed until a long term injury to Middlebrooks changed the equation.

 

[Hoplite]

You're neglecting the fact that I was right. Despite the poor defensive play by Bogaerts, Drew want signed until a long term injury to Middlebrooks changed the equation.

 
Hahaha, classic.

 

[HriniakPosterChild]

 
Hence the question, when was the last time a big name free agent stated that they did not want to re-sign with a big market team they left as a free agent? I'm sure someone was dumb and angry enough to do it at some point.

Ken Griffey Jr. forced a trade from Seattle to the Reds by saying exactly that.

 

[Rasputin]

Hahaha, classic.

With the extra added value of being true.

 

[Hoplite]

With the extra added value of being true.

 
Greatest baseball mind of our generation.

 

[Rasputin]

Greatest baseball mind of our generation.

Yeah, Branch Rickey has nothing on me.

 

[JimBoSox9]

I find it hard to believe that so many are dissecting the fairly boilerplate messages coming out of Lester's camp as affecting the probabilities of what happens. FA loves the city and team and wants to say, doesn't want to negotiate while playing, all the while leaking numbers that could make the latter not so.

You're looking for truth in kabuki, and it wouldn't hold water for a moment if people didn't have strong feelings for JOHN F'ING LESTER. There's too big a gap between what we know about the Sox offers and Lester's asking price, and too short of a time before FA, for this to get resolved.

$50 to the Jimmy Fund against anyone who thinks Lester will sign before FA.
 
Edit: clarity

 

[Rovin Romine]

Let's not forget that Lester had that quote about Pedroia being the highest paid second baseman when Pedroia signed and thus he didn't depress the market for second basemen (or some such.)
 
I wouldn't be surprised if Lester thinks a home town discount is something like "FA Maximum Offer" - 10%.  If that's the case he's gone.  Lester's going to be grossly overpaid by someone in FA.  I can't imagine the Sox would want to only massively overpay him.   Especially if 2015 is a "maybe" season, should the Sox decide to go with mostly rookie players.  

 

[glennhoffmania]

I don't understand why Lester's representatives and the FO having further discussions right now would distract Lester or the team.  It's not like Lester would be called into daily meetings to discuss the details instead of getting his work in.  It's not like Ben is calling Lester late at night to float another idea by him.  Lester could simply tell his agent what his floor is and to let him know if/when the Sox ever offer something close.  And if neither the agent nor Ben leak anything to the press there are no questions for other players to answer.  In other words, I don't buy the excuse that talks are being put on hold to avoid any distractions. 

 

[BosRedSox5]

I don't understand why Lester's representatives and the FO having further discussions right now would distract Lester or the team.  It's not like Lester would be called into daily meetings to discuss the details instead of getting his work in.  It's not like Ben is calling Lester late at night to float another idea by him.  Lester could simply tell his agent what his floor is and to let him know if/when the Sox ever offer something close.  And if neither the agent nor Ben leak anything to the press there are no questions for other players to answer.  In other words, I don't buy the excuse that talks are being put on hold to avoid any distractions. 

 
I think it was Ken Rosenthal who said that one of the dangers was the possibility of a leak. I know this club traditionally runs a tight ship, but you never know. It's possible that the team could offer Lester something that the fan base thinks is fair (there's a lot of idiots out there commenting on NESN and WEEI articles who think 3/30 is fair) and if he rejects it, fans might turn on him. I would think most SOSHers would understand if he turned down 120/5 and pushed for 6 or 7 years but there's a lot of people who have unrealistic expectations. 

Maybe you're on to something with Lester and his agents. I remember back when Mike Mussina was a free agent, he allegedly told his agent that he wanted to sign with the Yankees and to just make it happen. Obviously Arn Tellem did really well for him, but I think there's precedent for something like that. 

 

[dcmissle]

Club traditionally runs a tight ship? The place has been leaking machine with a history of PR disclosures that extends as far back as Burleson, Fisk and Lynn in circumstances like this.

I hope that this has changed under Ben, and also people above him who have a recent history if this kind of stuff exploding in their faces. I also hope that nobody in any position of influence is moronic enough to believe that public fencing with Lester is going to do anyone any good. But Lester has a right to be wary. I certainly would be.

 

[Drek717]

I don't understand why Lester's representatives and the FO having further discussions right now would distract Lester or the team.  It's not like Lester would be called into daily meetings to discuss the details instead of getting his work in.  It's not like Ben is calling Lester late at night to float another idea by him.  Lester could simply tell his agent what his floor is and to let him know if/when the Sox ever offer something close.  And if neither the agent nor Ben leak anything to the press there are no questions for other players to answer.  In other words, I don't buy the excuse that talks are being put on hold to avoid any distractions. 

Until it gets into the media, which is example Lester has used recently for why it can be a problem.
 
I still do not think that the AAV is the sticking point as much as the years.  Lester said he'd take a discount for the same kind of security as what Pedroia got.  Well, Pedroia got enough years added on to his existing deal to carry him into his late 30's.  The Sox are likely thinking 4-5 years while Lester wants at least six, preferably 7.
 
To that end, I'd really like to see the Sox put out a 7/$140M offer.  If he hits FA he'll probably get at least 6/$140M from some team willing to overpay.  The Sox could probably settle all this now and effectively get a "free" age 37 season over his free market value if they'd just commit to what the guy has said he wants - to retire a Red Sox.

 

[TheoShmeo]

Even if there were leaks, so what?  Lester has pitched on the biggest stage under the most pressure imaginable.  He's been a starter for two WS champs.  A media report here or there on contract negotiations seems like small potatoes compared to that kind of pressure.  And it's not as if a distraction is going to make much of a difference.  The Red Sox are on the verge of being hopelessly out of the race and are playing as listlessly as they have in a long time.  A few distractions from the present boring and painful reality might do them all good!
 
To me, Lester shutting down negotiations right now sounds like code for "these guys had their chance to get something done early on, they had the balls to start the negotiations off with a ridiculous offer, they diddled around thereafter for months, I'm pitching lights out right now and I may as well check the market after this year ends."  And the internal narrative could reasonably be worse; he could be annoyed at their approach and have determined to go elsewhere.

 

[glennhoffmania]

Until it gets into the media, which is example Lester has used recently for why it can be a problem.
 
I still do not think that the AAV is the sticking point as much as the years.  Lester said he'd take a discount for the same kind of security as what Pedroia got.  Well, Pedroia got enough years added on to his existing deal to carry him into his late 30's.  The Sox are likely thinking 4-5 years while Lester wants at least six, preferably 7.
 
To that end, I'd really like to see the Sox put out a 7/$140M offer.  If he hits FA he'll probably get at least 6/$140M from some team willing to overpay.  The Sox could probably settle all this now and effectively get a "free" age 37 season over his free market value if they'd just commit to what the guy has said he wants - to retire a Red Sox.

 
Yeah I still don't see that as enough of a reason to end talks due to distractions.  The media will talk about this and invent stories whether they're actually negotiating or not.  Lester isn't sitting at the table or having conference calls.  Reporters, or alternatively someone like Cafardo, will continue asking him questions and it can't be avoided.  So I think one of two things is going on here: 1)they are in fact talking but Lester doesn't want to make that fact public; or 2)they aren't talking because Lester's pissed and he's using the distraction angle as an excuse.

 

[jimbobim]

Can't access twitter from my computer from work but this tweet 20 mins ago from Gammo scares the shit out of me 
 
"While many of us believe Red Sox should sign Lester 5/120 what happened to Sabathia after 32 and Halladay after 33 are cautionary tales"  
 
Sabathia and Halladay have a lot more in common then breaking down on the other side of 30. They were both traded when teams didn't want to/ didn't have the resources to pay them and field a competitive team. 
 
If the Red Sox are that skittish about ponying about big money for a pitcher about to be in his 30's I get it. I really do . It's very rational but it makes life exponentially harder for them. If they don't want to pay him then it does them and him no good for him to continue being an ace for a team that can't hit its way out of a paper bag.
 
Lester on the market is the definition of a rental and with the A's cashing in their chips for Shark, Price is the next top flight option option available for a contender . He also has a year left which as both Beane and Cherington have publicly acknowledged is a huge consideration when parting with top 5 or 10 prospects. A team trading for Lester probably would want some idea of what he's going to demand to try and resign him so the prospect price isn't only for a year of returns. 
 
Unfortunately the most pitching needy team is the Yankees which is a non option. Maybe the Angels , Mariners, and Dodgers could be enticed into a bidding war to add Lester but again the return would have to be huge and primarily focused on offensive talent that is ready to contribute for at least next year which is the hottest commodity in the game. Additionally, those teams also know how much pressure the Sox would be under to get something.
 
Trading aces is almost as much of a crapshoot in terms of what you get as the ROI on the big contract they end up signing. Pitching unpredictability and attrition is part of the game and unavoidable if you ask me.  
 
Also you can pretty much book it he'll be in pinstripes next year if he hits FA. Cashman has no farm system to speak of and CC Nova and Pineda as massive question marks.    

 

[glennhoffmania]

Sabathia's been throwing 200+ innings in the majors since age 21.  Lester didn't come close until he was 24.  Comparing Sabathia and Lester only based on age is almost totally useless.

 

[Smiling Joe Hesketh]

Halladay had 2046 innings on his arm when he went to Philly and had about 2500 on it when he started breaking down. Sabathia had 2550 innings on his arm when he started having his bad seasons (2013-2014).
 
Lester currently has 1500. Say he's up to 1600 by the end of the year. Another 5 year deal at roughly 200 innings a year gets him to around 2500-2600. So I don't think the comparison holds at all. Lester's arm is a bit fresher.