Jon Lester contract poll

[bankshot1]

Given every fact, opinion or bias that you hold concerning Jon Lester, his pitching abilities, as well as his personality, and fit with the Sox, and your knowledge about the Sox, including the team's composition now and how you see it in the future, needs now and in the future, payroll commitments, the front office and track record for scouting  and developing players, the prospects currently in the minors, free-agent pitchers, or pitchers you may be able to trade for, the competitive landscape of both the AL East, and the AL, or any other factor you believe relevant, if Jon Lester's agent gave you a call and informed you Lester's bottom line, was a 6 year deal for $150 million, would you sign him to that contract, or would you inform the agent, tell Jon we're going to pass?  

 

[Bone Chips]

Nope. Not at that price. The Sox missed their opportunity to sign him to a deal that makes sense. Don't send good money after bad. Trade him and get the maximum value you can, which will also increase the odds of him not winding up on the Yankees.

 

[jimbobim]

I would rather have it be 140ish but having waited this long and seeing as Lester is in full contract year mode with no palatable alternative I think they have to get it done. Lester's potential trade return is significantly hurt by him being a complete rental. 

 

[Plympton91]

I'd counter with 7/$140 and see what he said. I'm more concerned about the AAV being too high than I am that the length will be too long.

 

[Dan to Theo to Ben]

$150 mil USD is pretty close to Lecter transfer fee, no? 
 
I'd rather would have had Ells, but I vote yes on Lester. 

 

[glennhoffmania]

That's definitely on the high end and doesn't reflect any hometown discount, but we're talking about possibly an extra $5m in AAV over the next 6 years when supposedly, and hopefully, a good portion of the roster will be comprised of low-cost players.  Given the alternatives, such as signing another pitcher to an even bigger deal or trading a bunch of prospects, I'd do it and cross my fingers.

 

[vadertime]

Not a chance.  After seeing the decline of Verlander & Sabathia I am not going beyond 3 years.  Overpay on a short term deal.  Offer something like 3 years and 90 million or 2 years 56 million.  Would he take that? Probably not, but it is what it is.  And if he gets that bigger deal from somewhere else more power to him. I hope he goes on to win 100 games and multiple Cy Youngs with that team.  I'm not overpaying for sentimental reasons and limiting future spending just to appease a fan-base.

 

[snowmanny]

Back in May I was one of the few posters who said I'd consider 6/144. I was expecting a signing a bit lower than that: 5/110 or something. 6/150 is pretty high but I'd probably do it given the totality of the circumstances.

There is salary cap room. The Red Sox seem to have stopped bidding, or at least bidding aggressively, on international major league level players. What's the alternative? Outbidding everyone else in money or prospects for some other comparable pitcher? Getting lucky on the next Bartolo Colon?

 

[Doc Zero]

Spend the money and build the rotation around him.

 

[bankshot1]

I tried to pick terms that would approximate what a top of the rotation FA starting pitcher would command  in this market. I do not think there's a perfect price, but one that either works or (doesn't work) for the player and team. I just want to get a sense of how a reasonably well informed population would shake out.

 

[ManhattanRedSox]

I'd counter with 7/$140 and see what he said. I'm more concerned about the AAV being too high than I am that the length will be too long.

I voted no as well.  Take face value, I think this contract is not going to be as great out in year 5-6.  That said, if there were performance benchmarks/escalators that would get to the 6/150, I'd change my vote to yes.  I just don't get a great feeling shelling out that kind of coin for a guy with a lot of innings and north of 30.  Iconic player or not.  Yes, it would suck if the NYY swoop in and throw a Brinks truck at him - but I don't see the tail end of that contract being all that great for the team - nor any indication of a home town discount that others have alluded to.

 

[glennhoffmania]

I'd be curious to see a poll with options like this:
 
1. 6/100
2. 6/110
3. 6/120
4. 6/130
5. 6/140
6. 6/150
7. None of the above
 
to see what people's cutoff is, and then read why they chose that cutoff.  But I'm not going to start a third Lester thread, and second Lester poll, on the main board.

 

[mfried]

Given every fact, opinion or bias that you hold concerning Jon Lester, his pitching abilities, as well as his personality, and fit with the Sox, and your knowledge about the Sox, including the team's composition now and how you see it in the future, needs now and in the future, payroll commitments, the front office and track record for scouting  and developing players, the prospects currently in the minors, free-agent pitchers, or pitchers you may be able to trade for, the competitive landscape of both the AL East, and the AL, or any other factor you believe relevant, if Jon Lester's agent gave you a call and informed you Lester's bottom line, was a 6 year deal for $150 million, would you sign him to that contract, or would you inform the agent, tell Jon we're going to pass?  

No. I simply think that he could be had for a bit less: say, 5 years $125 mil.

 

[Eck'sSneakyCheese]

I said no, but I wouldn't be upset at either party if that's what happens. This is also coming from someone who thinks Kershaw is overpaid but understands that the landscape of salaries is changing drastically.

 

[P'tucket rhymes with...]

If I'm in an FO that wants to keep the contract as short as possible, I'd ask Mr. Agent if his client would be interested in 5/125 with two more team option years at $22 each.  I'd assume he'll want the guaranteed sixth year, although I don't think I'd go over $140 and would rather see it at $132 for six.

 

[TheYaz67]

I'd be curious to see a poll with options like this:
 
1. 6/100
2. 6/110
3. 6/120
4. 6/130
5. 6/140
6. 6/150
7. None of the above
 
to see what people's cutoff is, and then read why they chose that cutoff.  But I'm not going to start a third Lester thread, and second Lester poll, on the main board.

 
Well, I think my cut off for starters is 5 years max, and I strongly suspect that the team's is as well, so I would be none of the above for all those. 
 
No reason something like $110M-$120M/5 years is not doable, in that it pays him a bit extra for the lack of a sixth year - if he is serious about the "home town discount part"....

 

[jscola85]

I'd do either 5/$130 (shorter, high AAV) or 6/$140 (longer, slightly discounted AAV) but giving the extra year and $25M AAV is a bridge to far for me.

 

[glennhoffmania]

 
Well, I think my cut off for starters is 5 years max, and I strongly suspect that the team's is as well, so I would be none of the above for all those. 
 
No reason something like $110M-$120M/5 years is not doable, in that it pays him a bit extra for the lack of a sixth year - if he is serious about the "home town discount part"....

 
I first had some 5 year options but I think his comment about wanting to finish his career with Boston makes 6 years the minimum.

Also, if you'd do 5/120 why wouldn't you do 6/120?  Same amount of cash, lower AAV, and a chance he's worth at least something in year 6.

 

[mwonow]

One of the things that's always been great about the BB Pats was the "middle class" - guys who earned less than top pay at their position, but more than roster fillers. Though time, this has served the Pats better than the approach used by, say, the Colts, or even the Jets.
 
This, though, is a different situation. Given the paucity of FA talent, and the richness of the prospect pipeline, it looks as though the Sox will have quite a lot of cost-controlled talent, and a lot of budget room for a handful of high-priced pieces. Where do you want to spend? I'd like "power" and "starting pitching." Lester is a good fit with the latter - and at this stage, I'm more concerned with getting the best 25 players on the field than with adhering to the "set a value on the player and stick to it" approach that works in football, but might not apply as well here.

 

[brienc]

I voted yes. Of course, I'd rather see Lester sign for less, but it's not worth losing him over $10 million. I also think his contract will seem pretty reasonable in a few years, with the market for top FA pitchers being what it is.

 

[Snodgrass'Muff]

I wouldn't hesitate to sign him for 6/140 so if he's offering to end the process right now and allow me as the hypothetical GM to focus on what I'm going to do this deadline to prepare for 2015, then yes, I'll sign that deal.  The extra 10 million is worth the freedom to turn around and shop Lackey while he has an artificially inflated level of value, and to know I won't need to spend prospects on replacing Lester's production for the next few years which frees them up for filling holes or bringing back a middle of the order bat.  I probably wouldn't go much higher than 150, but given the timing of that offer, yes, I take it.

 

[IpswichSox]

The extra 10 million is worth the freedom to turn around and shop Lackey while he has an artificially inflated level of value, and to know I won't need to spend prospects on replacing Lester's production for the next few years which frees them up for filling holes or bringing back a middle of the order bat.  I probably wouldn't go much higher than 150, but given the timing of that offer, yes, I take it.

 
Really? There's no way on earth I would shop Lackey. If Lackey can sign an extension for relatively short years that discounts AAV somewhat as compensation for the $500k he's scheduled to earn next year, I think that's a solid ROI.  And I don't think the value in trading him would be higher than the value he has to our rotation as we integrate the kids. We still need deep depth next year, and a front three of Lester, Lackey and Buchholz with two kids sprinkled in makes me a lot more comfortable than a rotation with two veterans and three kids, which I don't think is sustainable (i.e., Middlebrooks, Bradley and Bogaerts).  

 

[HillysLastWalk]

Not a chance.  After seeing the decline of Verlander & Sabathia I am not going beyond 3 years.  Overpay on a short term deal.  Offer something like 3 years and 90 million or 2 years 56 million.  Would he take that? Probably not, but it is what it is.  And if he gets that bigger deal from somewhere else more power to him. I hope he goes on to win 100 games and multiple Cy Youngs with that team.  I'm not overpaying for sentimental reasons and limiting future spending just to appease a fan-base.

 
Current Innings Pitched:
 
Lester - 1505.1
Verlander - 1901
Sabathia - 2821.1
 
I understand the concern, but Lester doesn't have the innings that the others do.  Plus, and I could be wrong, Verlander might be more reliant on a power fastball than Lester (cutter).  With Lester also being a lefty.  Lastly, Lester's body type would be more desirable than CC's.

 

[Savin Hillbilly]

I said no. If I'm Ben, I could go six years, or I could go $25M. I can't do both. My options would be:
 
4/108
5/120
6/135
 
Take one of those, or leave them all and good luck to you.

 

[normstalls]

These are probably arbitrary, but I have internal cutoffs right about:
 
5/115
or
6/126
 
If he is willing to cut a year off, I'm totally fine with 23 million per year.  At this point I 'm pretty sure he does not sign either one of those deals, but that's about where I would draw the line.  Long-term, expensive pitching is just so risky.  The obvious flip side is you need a couple studs to anchor a staff to win a WS.  The Sox front office is obviously in a very difficult position.

 

[Brianish]

Like many, I would offer 6/140, but the Sox have a better sense of how firm Lester's camp is on 6/150. If they feel that's really the only way to sign him, I would swallow it. He's got next to no injury history. For that reason, I'd give him a contract I wouldn't give others. 

 

[Snodgrass'Muff]

 
Really? There's no way on earth I would shop Lackey. If Lackey can sign an extension for relatively short years that discounts AAV somewhat as compensation for the $500k he's scheduled to earn next year, I think that's a solid ROI.  And I don't think the value in trading him would be higher than the value he has to our rotation as we integrate the kids. We still need deep depth next year, and a front three of Lester, Lackey and Buchholz with two kids sprinkled in makes me a lot more comfortable than a rotation with two veterans and three kids, which I don't think is sustainable (i.e., Middlebrooks, Bradley and Bogaerts).  

 
I'd rather cash in on his inflated value now than gamble on him not declining in his age 36-38 seasons.  I agree that Lester, Buchholz and the kids is a thin rotation and would require some good luck to pan out, even with Workman and RDLR looking pretty good this year, but they have the money to pursue a short term free agent who could replace Lackey for around what you'd end up paying him anyway, but at a younger age.  Gavin Floyd, Justin Masterson, Ervin Santana, and James Shields are all free agents and would fall in well below the Scherzer AAV range.  I wouldn't even hesitate to bet on any of them over Lackey at similar money for the next three years, with the possible exception of Masterson, though if you can get him cheaper than Lackey, he may be worth the risk.
 
It all depends on the return for Lackey, however.  I'm looking for a top 50 prospect.  Preferably a corner outfielder with some pop.  I mentioned this in another thread, but David Dahl or Jesse Winker are both enticing.  The Red are in contention and should be happy to upgrade their rotation with Lackey.  The Rockies seem to think they can crawl back into it, and Lackey would be a huge help in that.  You could also look at the two bats most of us wanted in last year's draft, Clint Frazier and Austin Meadows.  Neither the Indians nor the Pirates are likely to be looking to move them, but both have reasons for their clubs to be a little down on them Frazier hasn't been great in his first year and Meadows is hurt.  Chances are both clubs aren't interested in a swap for Lackey, but it's worth a phone call.  Both could use some help in the rotation and both are hoping to go to the playoffs.
 
If there isn't a good return out there for Lackey, you don't trade him.  Given the somewhat unique circumstances regarding his contract for next year, however, and given the return for Samardzija, I think you should absolutely shop Lackey if you've got Lester locked up already.

 

[Stitch01]

I voted no, but I don't feel great about it given the alternatives will all be overpays too

 

[IpswichSox]

 
Gavin Floyd, Justin Masterson, Ervin Santana, and James Shields are all free agents and would fall in well below the Scherzer AAV range.  I wouldn't even hesitate to bet on any of them over Lackey at similar money for the next three years, with the possible exception of Masterson, though if you can get him cheaper than Lackey, he may be worth the risk.

 
Maybe I'm underestimating what Lackey could be signed for. But I would think something like 2/$25M or 3/$30M? The Red Sox do hold significant leverage -- he can retire or he can pitch for $500k next year. Or behind door No. 3 is a multiyear deal, which has to reflect the discount of the $500k salary. Masterson, Shields et al are all going to get three and four times the amount I'm proposing in a multiyear deal for Lackey.  

 

[Snodgrass'Muff]

 
Maybe I'm underestimating what Lackey could be signed for. But I would think something like 2/$25M or 3/$30M? The Red Sox do hold significant leverage -- he can retire or he can pitch for $500k next year. Or behind door No. 3 is a multiyear deal, which has to reflect the discount of the $500k salary. Masterson, Shields et al are all going to get three and four times the amount I'm proposing in a multiyear deal for Lackey.  

 
It will take a higher AAV and more years, but on guys who are a little younger I'm okay with that.  Essentially, I'd rather have a prospect like Winker or Dahl and someone like Floyd at 13 or 14 AAV on a 4 year deal than Lackey on 2/25 or 3/36 or so.  It's all hinging on the return, though, and this is ancillary to the Lester contract talk, so I'll just leave it at that.

 

[MakMan44]

I wouldn't hesitate to sign him for 6/140 so if he's offering to end the process right now and allow me as the hypothetical GM to focus on what I'm going to do this deadline to prepare for 2015, then yes, I'll sign that deal.  The extra 10 million is worth the freedom to turn around and shop Lackey while he has an artificially inflated level of value, and to know I won't need to spend prospects on replacing Lester's production for the next few years which frees them up for filling holes or bringing back a middle of the order bat.  I probably wouldn't go much higher than 150, but given the timing of that offer, yes, I take it.

This is pretty much where I'm at as well. 
 
Furthermore, I'm not incredibly interested in extending these contract discussions past the post WS exclusivity window. If you have to pay a bit of a premium now to avoid that, I'd do it in a heartbeat.  

 

[rembrat]

It's interesting that people are essentially haggling over an extra $10-15MM which is nothing to this franchise. I voted YES.

 

[snowmanny]

Was talking about all their $$$ and then capitalizing "yes" done by purpose?

 

[P'tucket rhymes with...]

It's interesting that people are essentially haggling over an extra $10-15MM which is nothing to this franchise. I voted YES.

Everyone has to draw their own line someplace.  If there's such a thing as collective wisdom around here, the relatively even split in the poll right now suggests that the contract is going to end up right in that $140-150 neighborhood we're haggling about.

 

[jacklamabe65]

4 for $120,000,000
 
Philosophically, that would make the point about the declining numbers of a pitcher in his thirties but overpaying him for those years in which he could still be an ace.

 

[Rasputin]

I have qualms about the deal but I think the next three years and the need for someone to anchor the rotation while the kids make the transition are important enough that I'm willing to take the risk.

 

[HurstSoGood]

5 years @ $20-$21M ($100-$105M) with a team option for the 6th season. Kershaw's $30M annual contract has skewed the scale, but Clayton is also younger and is pitching like he's the best.
 
I worry that Lester is outperforming his averages this year, but will regress to being consistently "Above Average."  Do we feel he is one of the Top 5-10 pitchers in the Majors? How about just the American League? I say "no" and that $20M a year is an appropriate hometown discount. Anything more is pissing away money.
 
So, in a nutshell: 
I would not pay him 6/150.
The Red Sox might.
Some other team would almost certainly do it. 

 

[Riggs]

If I'm in an FO that wants to keep the contract as short as possible, I'd ask Mr. Agent if his client would be interested in 5/125 with two more team option years at $22 each.  I'd assume he'll want the guaranteed sixth year, although I don't think I'd go over $140 and would rather see it at $132 for six.

This is where my head is too in terms of the option. 5 yr, player option for 6, club option for 7.

Unfortunately Mr. Market has moved. If we don't lock him down before the end of the break I fear it will make it to the market after the season and the numbers that will be thrown around will be utterly stupid.

 

[wade boggs chicken dinner]

If it were me, I'd do it but that's because I love Lester and it's not my money. 
 
However, I doubt the Red Sox are going to go six years for him.  It would be great if they did, but opening with 4 years makes six hard to fathom.
 
If Lester hits FA, he's going to get seven years easy. 

 

[BosRedSox5]

Jon Lester is invaluable to the Red Sox. If we replaced him with someone of similar age and ability we'd still be taking a huge step down IMO. 

 

[Lynchie]

I'd do 4 / 100 with an apology for the low ball offer. The years would be the discount and then he could be a free agent again at only 34.

 

[NDame616]

I'd do 4 / 100 with an apology for the low ball offer. The years would be the discount and then he could be a free agent again at only 34.

 
I'm sorry, but at this point I think $100M is a low-ball offer. I don't think there's anyway he doesn't get $125M+, and I wouldn't be surprised if the Yankees give him close to $200M. 
 
Lester is setting this up PERFECTLY to save face and leave by taking the highest offer. "Read what I said the whole season. I said I was upset at the first offer and if the Red Sox really wanted me they would have to give me my fair price. I went out to FA and found out what my fair price was and I gave the Red Sox every opportunity to match or come close to the numerous offers I was given (in the $130-160M range) and they wouldn't. It's a real shame they just didn't want to sign me."

 

[Lynchie]

No need to be sorry for an opinion.

 

[Harry Hooper]

A 4-year offer with a fat AAV and a sweetener for the 2014 season's salary might have had a chance back in ST, but I doubt it. It would have been a platform for getting to a 5-year extension, however. Now, anything less than a 6-year contract would be a surprise.

 

[Leather]

Jon Lester is invaluable to the Red Sox. If we replaced him with someone of similar age and ability we'd still be taking a huge step down IMO. 

 
Why?

 

[ookami7m]

I have qualms about the deal but I think the next three years and the need for someone to anchor the rotation while the kids make the transition are important enough that I'm willing to take the risk.

 
This is where I am as well. I'd go 5/120 but the 6th year seems like a bad idea if it's guaranteed.

 

[NDame616]

A 4-year offer with a fat AAV and a sweetener for the 2014 season's salary might have had a chance back in ST, but I doubt it. It would have been a platform for getting to a 5-year extension, however. Now, anything less than a 6-year contract would be a surprise.

 
I still think the conversations start at 6/128M or so, and escalate from there. The Yankees, Cubs, Tigers, Mets etc could all be in on Lester, which usually equates to contracts getting very bloated, very quickly.

 

[Rasputin]

 
I still think the conversations start at 6/128M or so, and escalate from there. The Yankees, Cubs, Tigers, Mets etc could all be in on Lester, which usually equates to contracts getting very bloated, very quickly.

Or Lester could want back as much as he says and is willing to take the first six year offer in that neighborhood that he gets.

Pretending that we know what will happen is silly.

 

[LondonSox]

Personally I think either screwed up, and underestimated the increaing price of contracts due to the lack of premier free agents and the revenue increases. In which case they screwed up, and MAYBE the own up to that and pay up, but I wou;d be surprised.
 
Or, they don't want to pay aging guys big contracts and never intended to sign Lester unless it was on their terms, in which case they clearly won't match what some others will be willing to pay.
 
I personally would overpay to keep it short, I don't want an old broken down Lester at 35/36 as the team gets expensive and contracts need to be redone.
 
The team will almost certainly be very cheap the next few years, I'd be far happier significantly overpaying the next 3-4 years, than going longer. We know that there are a string of cheap rookies coming through. And a lot of cheap but uncertain performance. Having a stud NOW that wants to be in Boston is great. Having him decline and be expensive as you start to need to extend X etc not so great.
 
I very much doubt Boston will go this high, for this long (nor would I). And we may never know if they screwed up, or have a policy on this kind of free agent (unless they sign a similar player to a similar deal, then it suggests they just screwed up the negotiations).

 

[Remagellan]

Jon Lester is our Adam Wainwright--the ace who takes the pressure off all the young guns coming up.  The Cards gave Wainwright a 5 year deal worth 97.5 million and he's two years older and has missed a year with an arm injury.   I have no problem with the Sox going 5 or 6 years on Lester in 20-25 million dollar range.  This team has money, and if our team is going to be replete with more and more cheap, young players, we can splurge on quality guys who want to be here.