Extending Lester
- Thread starter The Talented Allen Ripley
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I am normally against long, expensive contracts, but in the case of Lester, I think this is the ideal situation to make an exception. He should be productive throughout the length of a six-year deal. They have a need. And the payroll can handle it. Moreover, the alternatives are not that palatable. It gives the young guys time to work their way in. They will have enough prospects making their way up that they can afford it, and the fact is, he's been really, really good for Boston.
I think the post above is a good summary of how I feel about this. While you don't need a veteran pitcher for the next great Sox team it certainly helps and Lester is a bulldog. He's had a great track record of health other than what delayed the start of his career which had nothing to do with pitching.Snodgrass'Muff said:
Chances are this team barring some major trade/s or very rare rookie breakout/s is not going to seriously contend for two years. During this time, it would be great to have a pitcher on the staff that leads by example to show and lead what hopefully is at least two farmhands in the rotation. Most championship teams seem to have a nice blend of older veterans, prime of career players and rookies on the rise. So even though it's becoming more obvious by the day the Sox are rebuilding even if they won't admit it. I think that's a good thing if we'd like to contend year and year out as the Sox until recently have. I would like to keep at least 1 or 2 players around during the transition, as an example of what the farmhands should strive for, to play in one place for their careers. Is this overly ideal, sure, but to sell this ideal to even a couple of farmhands into signing a long term deal before they get to free agency will help the team be able to fill in team weaknesses through free agency and continue the cycle of contention like a relentless line-up.
I think the 5/120 mention in the article is just the floor that Lester and his people are willing to come to the table for. There is probably no chance he signs for that. It does give me hope for 5 years and a vesting option or five years with a team option and a buy out, though.
Get back to the table and don't dick around. Lock him up and turn your attention to the trade deadline and whatever your think is the best use of current resources for the future of the franchise.
Get back to the table and don't dick around. Lock him up and turn your attention to the trade deadline and whatever your think is the best use of current resources for the future of the franchise.
While I agree with the sentiment, you are overstating the $1M/player per year for former farmhands position. 3 to 4 years from now several players from this rookie class would be arbitration eligible and it's would likely to be very close to $2M/player per year for the average farmhand at that point. Your point still stands but don't overstate it.Plympton91 said:
If 5/120 is the invitation Lester needs to re-engage in discussions, why not send the invitation? At worst the Sox would discover they are light years apart and could plan accordingly, at best they reach a deal.
Unless they really have no interest in paying him $24 million/yr. in that case, at worst he would accept.bankshot1 said:
If having Lester at 5/120 is worst case for the Sox, they should probably pursue that path. However I imagine there are ways to sabotage talks if the Sox have no interest at those terms.Bob Montgomery's Helmet Hat said:
I'd agree, which is why they should open with a different, but comparable, offer. Something like 6/$132M. It drops the per year AAV by $2M a year but gives Lester an extra season. I think he'd take longevity over an extra year, meanwhile he's the kind of guy who is very likely to be worth $12M at age 36 in 2020 dollars. It would turn the tables a bit and stem the impression that the Sox aren't willing to commit to Lester retiring in Boston, while getting them a per year discount over a deal that they should be pretty ok with in the first place (the 5/$120M one).dcmissle said:
It seems the consensus here is it will take 6/150 to sign Lester. How much will Justin Masterson get this winter?
Lester is the better pitcher of the two, obviously, but by how wide a margin? If Masterson "only" gets 5/70, you could use the difference to fund a Jose Abreu-type contract for one of this year's crop of Cuban defectors.
Lester is the better pitcher of the two, obviously, but by how wide a margin? If Masterson "only" gets 5/70, you could use the difference to fund a Jose Abreu-type contract for one of this year's crop of Cuban defectors.
Bottom line...the Red Sox and his agent are the only ones who know about what it'll take. For all we know his agent said "We know we can get 7/160" back in the spring, and the Sox know they have to be close to that. Maybe the Red Sox have some idea what Lester will get as a FA, and have no desire to pay it.
Or perhaps Lester and his agents saw when CC went down that the Yankees will probably pay 8/200 for him.
Or perhaps Lester and his agents saw when CC went down that the Yankees will probably pay 8/200 for him.
Masterson unless something drastic happens is going to have to settle for a 1 year deal. He's been horrid. Would rather gamble on Webster or RDLR.maufman said:
I don't have it verbatim, but in ST this year when discussing the notion of a discount, Lester took pains to note he expected a discount as he wasn't a FA at that point and had a year to go on his contract. Obviously that appllies less and less as the season rolls on.
A lot has changed in the past decade -- there will be several teams willing to wager that Masterson's .339 BABIP and 66% strand rate are a fluke (not to mention, both those marks are likely to regress toward the mean during the second half). His 3.96 SIERA this season is roughly in line with his 3.84 career mark, and isn't dramatically worse than Lester's 2011-13 numbers.Tyrone Biggums said:
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Eddie Jurak said:
I just want to go back to this and say how much I appreciate an unusual, creative idea that makes rational sense for all sides. The MLBPA would go berserk, but if the FO entertained such an offer, I'd want to see them argue that this isn't in the interests of the player in question.
...And on the third hand, this scenario basically puts the price of our risk on the order of $17M/year, if we assume that his AAV on the upside (of $23M) would be the fair price for a Lester that was performing well in 2015. It's costing us $17M to delay making a decision on whether we believe in his longer-term prospects by one year. I wonder if that's a fair price for the "option" we're buying. If only we had some experts on financial options around here who could opine...
The 4/70 deal was made with the following hopes (looking toward 2015):
It's no longer a buyer's market for Lester. I was totally on board for the 4/70 offer. I've changed my tune completely. I think the FO should offer 6/135 with mutual options for a 7th year (player 5/ team 22.5). Lester is one of our guys and that means something to me.
- Lester said he would take a Pedroia like discount
- Buchholz was potentially going to come back in and pitch lights out for a whole season and nail down the role of staff Ace.
- Lackey- solid #2
- Doubront- solid #3
- RDLR/Workman/Ranaudo/Barnes/Webster all poised to potentially step in.
It's no longer a buyer's market for Lester. I was totally on board for the 4/70 offer. I've changed my tune completely. I think the FO should offer 6/135 with mutual options for a 7th year (player 5/ team 22.5). Lester is one of our guys and that means something to me.
A pitcher with knee issues causing declining velocity is not what we would need to replace Lester.MakMan44 said:
C4CRVT said:
The team shouldn't let that influence their decision. Of course, you can make a very compelling argument for signing Lester without any need for sentiment or fan attachments, and I don't think you were arguing that the team should care what you feel about Lester while negotiating with him. But it bears mentioning that how you feel about Lester in a Sox uniform doesn't really help us pin down what his value is to the Sox or another team.
No one is saying Masterson would "replace" Lester, in the sense of replicating his 2014 production, or even his projected 2015-20 production. I just suggested that maybe, just maybe, the difference in quality between the two is worth less than the difference in price is likely to be.lexrageorge said:
I don't think his value is really in question at this point. The floor is 5/110 +/- and I think that in order to avoid the PR hit and negative vibes (with the team) that come with coming off as cheap-skates, they should offer enough to make it clear to Lester that they want him to retire in red socks. The argument has already been made here for his durability and his value in the FA market IMO.
As a fan, I'm allowed to want to root for more than the laundry (or payroll efficacy). We've all followed his career for the past 12 years. He's a cancer survivor and by all accounts a great young man. I'm not arguing that this means he should be paid more than he would be on the FA market. I am arguing that it would mean something to me as a fan of the team (and most likely to him and to his teammates) for the FO to step up, see the writing on the wall and get out their checkbooks. Does anyone here seriously think he'll get less than 5 years?
It's all part of wanting to belong to something great. We all get to go to our graves saying that we were part of the teams with Pedroia, Ortiz and Lester on them. Three guys who's names should be forever part of my team's history. I don't want to share Lester with the Yankees or any other team. That's worth something to me over and above his WAR.
After this year, the fact that it would be good business (IMO) is turning out to be more and more a coincidence.
As a fan, I'm allowed to want to root for more than the laundry (or payroll efficacy). We've all followed his career for the past 12 years. He's a cancer survivor and by all accounts a great young man. I'm not arguing that this means he should be paid more than he would be on the FA market. I am arguing that it would mean something to me as a fan of the team (and most likely to him and to his teammates) for the FO to step up, see the writing on the wall and get out their checkbooks. Does anyone here seriously think he'll get less than 5 years?
It's all part of wanting to belong to something great. We all get to go to our graves saying that we were part of the teams with Pedroia, Ortiz and Lester on them. Three guys who's names should be forever part of my team's history. I don't want to share Lester with the Yankees or any other team. That's worth something to me over and above his WAR.
After this year, the fact that it would be good business (IMO) is turning out to be more and more a coincidence.
Sure, and I get all that. I even agree with a lot of it. If I had a say, I'd make sure Lester spent the rest of his career pitching for the Red Sox because I've grown attached to him as a player. I'm just not sure how that's terribly relevant in a discussion about whether the Sox should or should not extend his contract or re-sign him in the off season. There's nothing wrong with expressing a sentimental desire to see him stick around, but a number of posters have worked that into their overall points and the line has been blurred a bit, so I figured it was worth pointing out.
Sentimentality may not be the point but if we understand that baseball is entertainment and that Lester is entertaining to watch that should play a role in the business decision. His pitching shows variety, he ks people, he doesn't walk them and slow the game to a crawl. I want him on my team.Snodgrass'Muff said:
Sentimentality may well be useful in getting Lester extended here. Not as the pivotal factor, but certainly well in the mix.
It's going to be a long cold winter, competitively and marketing wise, if they lose him.
Masterson likely won't cut it.
It's going to be a long cold winter, competitively and marketing wise, if they lose him.
Masterson likely won't cut it.
The argument's been made in the "without Lester" thread that if the Red Sox don't extend or sign him, they're not going for Scherzer, either. That seems right.
The more I think about it with that in mind, the more I want to see them sign Lester because letting him go is pretty risky. If Clay had been able to be good, consistent, and healthy, it would be different. Given his actual performance, and Doubront's awfulness: if you give up Lester as the anchor, you're betting on a lot of good performances from pitchers without much of a track record, or a really variable one. (Outside of Lackey, if we have him.) After what happened with the hitting this season, that's uncomfortable.
EDIT: Lackey
The more I think about it with that in mind, the more I want to see them sign Lester because letting him go is pretty risky. If Clay had been able to be good, consistent, and healthy, it would be different. Given his actual performance, and Doubront's awfulness: if you give up Lester as the anchor, you're betting on a lot of good performances from pitchers without much of a track record, or a really variable one. (Outside of Lackey, if we have him.) After what happened with the hitting this season, that's uncomfortable.
EDIT: Lackey
Even if you believe the Sox must start 2015 with a "front line" starter, their options aren't limited to Lester and Scherzer. There's an excellent chance that David Price, Cole Hamels and Cliff Lee will all be available between now and next spring (though one or more of them might move in the next few weeks, particularly with the MFYs having an acute need).tomdeplonty said:
The FO might prefer to trade prospects and/or accept injury risk in exchange for making a shorter commitment than the six years that most of us think Lester will demand (or in the case of Price, having greater certainty that the guy they're paying like an ace will actually pitch like one). The Peavy deal a year ago is a lower-stakes version of what a trade for Hamels or Lee might look like.
I can't see Price because he would cost a huge haul in prospects to a division rival and probably wouldn't sign for anything less than 8/$200M.
It will really piss me off if the Sox lose Lester (especially to the Yankees) and wind up signing James Shields for more than they could have had Lester for in the spring.
It will really piss me off if the Sox lose Lester (especially to the Yankees) and wind up signing James Shields for more than they could have had Lester for in the spring.
dcmissle said:
I would say there's more sentimental attachment to Lester than Ellsbury. Perhaps it was him overcoming cancer, his general durability, his personality, or just pure randomness, but Lester seems to have a closer bond with the fans than Ells ever did. Couple that with the fact that the Sox are highly unlikely to win a WS this year and there will be a lot more hand-wringing about letting Lester go than Ellsbury.
Price is much more likely to be worth 8/200 than Lester is to be worth 6/150, but I agree that the cost in prospects is likely to be unacceptable -- if the Rays were willing to trade Price for a prospect of X's caliber, he'd probably be pitching in Oakland now.curly2 said:
If the options are (1) sign Lester, (2) sign Shields or Scherzer, (3) trade for someone like Hamels or Lee to avoid a 6-year commitment, (4) sign a lesser SP and spend the difference on hitting, and (5) trade for Price, I think a Price trade is by far the least likely to happen.
I think this is right. This is the guy who was almost traded for ARod, and instead overcame cancer and won two world series and threw a no-hitter and made Francona cry. This is the guy who wasn't supposed to be mentioned in the same sentence as Buchholz, Hughes, Chamberlain and Papelbon and has eclipsed them all. He's been up and down, a little, but has made all his starts and has been a horse at the most important times.jscola85 said:
Maybe his numbers can be replaced. Maybe not. But you know there is some additional intrinsic value, at least to me, in watching this particular guy pitch for this particular franchise.
snowmanny said:
Totally agree. Say the Red Sox signed someone to "replace" Lester and over the next 5 years this guy was able to match Lester's on the field production exactly. I think you'd still be losing out.
Jon Lester has been remarkably consistent throughout his career and you might actually say there's some evidence that he's improving. He's walking fewer guys that ever. His WHIP, BB/9, and K/BB numbers are at their all-time bests. He's still got the skill, but more than that keeping homegrown prospects who still have a lot to contribute at a reasonable market rate is something the club should invest in. When you have someone like him in the organization for 9+ years they become a de facto face of the team. If they're a good guy, like Lester then that's a really good thing for your club. You have someone who represents the team, and who players look to for on the field leadership.
That may seem like "Captain Intangibles" type fluff, but I'm not so sure it is. Listen to practically any prospect or rookie interview and the thing all of them mention is who's made an impact on them. They gravitate towards guys and follow their lead. They care about the opinions of the veterans they respect and that keeps them in line.
If you have a long term position player like that, like Pedroia, and a long term pitcher like that, like Lester it seems like an ideal set up. Not only are the fans going to be getting more value out of watching one guy play all or most of his career with one franchise, but I think the franchise benefits in other ways from their leadership.
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.
At this point it would be nice if Lester just came out with a number to the Sox that he would take to stay, say $135MM for 6 years. Take it or leave it! Give the ownership the All Star weekend to figure out if that works. If they balk, he should just roll the dice in free agency, which means he is going to the highest bidder (probably not the Sox).
At least we'd know where to go with our pitchforks and torches when he signs with the Yanks for $150MM.
At least we'd know where to go with our pitchforks and torches when he signs with the Yanks for $150MM.
Hoplite said:
I think your estimate on their chances for re-signing him is insanely low and trading him probably isn't even the best way to maximize his value should they not come to terms. Lester has expressed a desire to remain in Boston, and reiterated it recently. If the team treats him fairly, they can work out a deal either now, or between now and next spring. The longer it takes, the more expensive it's going to get, but the deal is there to be made. So the extra time to work out that deal has value. Even if we look past that, however, the return on a Lester trade might not even be worth as much as the pick they'll get for a QO made over the winter. The pick itself and the slot money it adds are far more valuable than a pick was in the previous CBA. Keep in mind it also removes draft assets from the team that signs him. For a half a season of Lester, the best they can hope for is a top 50 prospect and even that is going to be tempered by the constraint of having to deal only with contending teams.
The best course of action is to work out a deal, assuming he's not demanding 30 million a year for 7 or 8 years or something else equally as preposterous. If he's looking for 22-25 million a year for 6 years, you have to come to terms. The only way trading him makes much sense is if the front office doesn't really want him back at any price and all the negotiation leaks are just for show. If that's the case, however, someone in the front office has lost their mind.
I fully expect the Sox to eventually sign Lester. They're just going to pay a bit more than they wanted to. It will still be less than Scherzer gets. They need pitching, have the available payroll space, and he's a homegrown guy and fan favorite.
Wait, if the front office doesn't want to commit $150 million to a pitcher over 30, then they've lost their minds?Snodgrass'Muff said:
I love Jon Lester, and I want him to pitch his whole career for the Sox. But I can understand how the economics might not work for the team. How many such contracts can we deem successful?
Bob Montgomery's Helmet Hat said:
That's not what I said. I said if they don't want him at any price they've lost their minds. It was an ancillary thought about what might drive them to want to trade him before the deadline.
snowmanny said:
Not at all, but I think it's hard for a lot of people to take that leap on Lester staying healthy. He's always been healthy, he's got good mechanics, he sees like a good candidate to stay healthy for 5-6 years but people will invariably bring up examples of pitchers who broke down during their 30's.
I say, so what. If you want elite talent in this league, if you want to keep a star around for his whole career then you need to pay them. We're not the A's or the Rays. We have the wherewithal to make a mistake. Look at Lester, he seems like a good bet to stay healthy so let's get it done. What are we going to do if we don't sign him? Get Masterson? Sign Scherzer? Go after James Shields? No, all of those options are inferior.
If this front office lets Lester go then yes, they've completely dropped the ball.
Snodgrass'Muff said:
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.
But I didn't ask who would have been worth it. I asked who did get such a contract and then earned it. I'm curious as much as anything.snowmanny said:
Lester, Shields, Sherzer, Price in a year, Samardzjia in a year all approaching 30 with their next contract taking them through at least 34 or 35
All pitchers of at the very least a decent track record that can demand between 100- 150 on the open market for being an "ace". We can quibble about the price tag ,definition, and applicability but as long as owners don't let players hit free agency untill they are 28-30 usually the return on investment might for year be useless for a pitcher if they have to get TJ. Example John Lackey
I think it ends up being 6 for 140 with some type of club option.
All pitchers of at the very least a decent track record that can demand between 100- 150 on the open market for being an "ace". We can quibble about the price tag ,definition, and applicability but as long as owners don't let players hit free agency untill they are 28-30 usually the return on investment might for year be useless for a pitcher if they have to get TJ. Example John Lackey
I think it ends up being 6 for 140 with some type of club option.
snowmanny said:
And they gave a 30 year old Carl Crawford a 7 year deal, a 29 year old Adrian Gonzalez a 7 year deal, and an 8 year deal to a 29 year old Pedroia. It wouldn't be out of character at all to make a long term commitment to a player who meets their criteria.
Bob Montgomery's Helmet Hat said:
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?
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