Extending Lester

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RedOctober3829

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While I see your point, this contract won't handcuff the Red Sox going forward. There's so much money coming off the books and cost controlled talent filling out the roster. If they sign Lester to a $25M AAV, it won't affect them as much as everybody thinks.
 

DeJesus Built My Hotrod

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RedOctober3829 said:
While I see your point, this contract won't handcuff the Red Sox going forward. There's so much money coming off the books and cost controlled talent filling out the roster. If they sign Lester to a $25M AAV, it won't affect them as much as everybody thinks.
 
To be clear, I agree that on the surface, it seems silly that the Sox would worry about the tail risk given Lester's amazing durability to date and his value as a staff ace.  However - and this is just a guess here - I suspect that a tail of $25mm per year tied up in a breaking down pitcher looks a lot more painful if they want to use to supplement the roster.   Its almost a certainty that, in order to compete, they will need to patch the holes that are inevitably going to be generated by some significant amount of that cost controlled talent not working out.
 

OCD SS

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ivanvamp said:
If they don't want to spend that kind of money for a 30+ year old pitcher, then it doesn't matter if his name is Lester or Hamels - they shouldn't want either.  
AFAICT the idea that the Sox will never give 6 years to a pitcher over 30 has never been explicitly stated by the Sox, it has only been brought up here as a reason why Lester has not been signed yet or may not be signed. But the truth is that the assumptions underlying these assumptions are just as unsubstantiated as the contract figures I through out:

Hammels represents cost certainty, and right now Lester doesn't; there is no evidence that 6/$130 or 6/$150 represent a deal Lester would sign now.

Right now the conventional assumption is that because he's been healthy for the past 7 years, Lester is likely to remain healthy for the next 6. It completely ignores that the Sox FO and medical staff might have better information.

Whatever you think of the initial, lowball offer, Lester responded with a contract year, 90th percentile performance. Based on simple aging curves and past specific examples, I understand being wary of high cost, long term contracts for players over 30, and pitchers specifically; I'm happy the FO is showing a bit of restraint and discipline after the way the last Yankee-esque spending spree worked out.
 

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RedOctober3829 said:
While I see your point, this contract won't handcuff the Red Sox going forward. There's so much money coming off the books and cost controlled talent filling out the roster. If they sign Lester to a $25M AAV, it won't affect them as much as everybody thinks.
 
Five or six years from now is exactly when all that talent will no longer be cost controlled if they're really good. There have been some pretty huge arb year contracts recently.
 

RedOctober3829

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Max Power said:
 
Five or six years from now is exactly when all that talent will no longer be cost controlled if they're really good. There have been some pretty huge arb year contracts recently.
Which is the exact time Lester will come off the books. It's such a no-brainer to sign Lester for these 5-6 years at around $25M.
 

wade boggs chicken dinner

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OCD SS said:
Right now the conventional assumption is that because he's been healthy for the past 7 years, Lester is likely to remain healthy for the next 6. It completely ignores that the Sox FO and medical staff might have better information.
 
 
We'll never know, but if the medical staff does have some information to which we're not privy or we're not really thinking about, it would make this thread pretty pointless.
 

Plympton91

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RedOctober3829 said:
Which is the exact time Lester will come off the books. It's such a no-brainer to sign Lester for these 5-6 years at around $25M.
And if they're as smart as they think they are they'll have another whole set of cost controlled talent coming online just as this set is getting expensive. Plus, they'll have kept some of the current crop at reasonable Napoli/Victorino AAV's by signing them to Pedroia like contracts.

There is no reasonable explanation for their refusal to sign Lester other than proprietary information they have about his health that flies in the face of every observable piece of evidence.
 

67WasBest

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soxhop411 said:
“@JMastrodonato: Jon Lester: "were all aware if what's coming next week." Said if he's traded, would still be open to re-signing with Red Sox”
https://twitter.com/JMastrodonato/status/492861549405831168

“@alexspeier: Lester said he'd be open to talking with Sox as free agent even if dealt. 'Why not? This is what I know. This is what I love.'”

https://twitter.com/alexspeier/status/492861576291295232
The best case scenario.  Add a prospect or two, then bring him back.  Always did make the most sense if they reached where they are in the standings.  IMO, If they were competing, the contract negotiations would be ongoing.
 

SouthernBoSox

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Jon Lester is the largest deadline piece in 2014. By a decent margin.

It's time to cash in. Best case is you resign him, worst case you cashed on with a couple good prospects to add to an already impressive system that allows for multiple big moves.
 

Yaz4Ever

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SouthernBoSox said:
Jon Lester is the largest deadline piece in 2014. By a decent margin.

It's time to cash in. Best case is you resign him, worst case you cashed on with a couple good prospects to add to an already impressive system that allows for multiple big moves.
This
 

Snodgrass'Muff

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It would bee stupid for Lester's camp to eliminate the Red Sox as a destination publicly as it would be one less big market team to drive up the price and one less division rival to push the Yankees with. Even if he's not interested in coming back I'm guessing they will keep having conversations with Ben to keep up pretenses.

Even still, that's comforting to read and makes me feel better about trading him.
 

Stitch01

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Snodgrass'Muff said:
It would bee stupid for Lester's camp to eliminate the Red Sox as a destination publicly as it would be one less big market team to drive up the price and one less division rival to push the Yankees with. Even if he's not interested in coming back I'm guessing they will keep having conversations with Ben to keep up pretenses.
Even still, that's comforting to read and makes me feel better about trading him.
Me too, although I still think Lester being traded than returning would be the single most shocking outcome
 

Idabomb333

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Stitch01 said:
Me too, although I still think Lester being traded than returning would be the single most shocking outcome
Why?  I haven't seen any comments from Lester that would indicate the opposite of the recent quote.  Certainly it's reasonable to think in general a guy would be upset about being traded, but I think it's at least equally reasonable to think Lester would understand.  I'd even describe it as not totally insane to think Lester might want to finish 2014 with a contender, and to have his market improved (only very marginally for a guy like him) by not having draft compensation associated.
 
I personally won't be shocked if this happens.  Every step of it makes sense to me.  The whole thing in combination makes for an unusual story, but so what?  I think it makes sense for Lester and the Sox if Lester gets traded.  I think if I'm Ben and I have approval to pay Lester what it takes to extend him right now, I would also be willing to pay a few extra million to sign him as a FA.  Lester should be happy because he gets to come back to Boston and gets essentially full market value.  Ben gets a significant prospect package, an improved draft position next year, and a few extra months to make sure nothing tragic happens to Lester's career before this giant new contract becomes official.  Ben loses, say, a 2-3 million a year over the life of the new deal (Does anyone have a good way to estimate that extra price?) and the exceedingly small chance that Lester would be enough to change the 2014 Sox playoff standing.
 
The only piece about this whole situation that could have made it a terrible idea would be if Lester took the position that trading him is an insult.  I think we now have sufficient evidence that's not the case.
 

Rasputin

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Excuse me for stating the obvious but if the Sox trade Lester, they can't talk to him until after the world series. If they keep him, they can talk to him from the end of the regular season until he signs somewhere else.

I don't know if I can stand an extra month of Lester posts.
 

NDame616

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Rasputin said:
Excuse me for stating the obvious but if the Sox trade Lester, they can't talk to him until after the world series. If they keep him, they can talk to him from the end of the regular season until he signs somewhere else.

I don't know if I can stand an extra month of Lester posts.
 
A bajillion posts aside, I don't think the window matters. No matter where he is after the season ends, WS ends, etc...he's going to test what every team wants to pay for him.
 

Stitch01

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Idabomb333 said:
Why?  I haven't seen any comments from Lester that would indicate the opposite of the recent quote.  Certainly it's reasonable to think in general a guy would be upset about being traded, but I think it's at least equally reasonable to think Lester would understand.  I'd even describe it as not totally insane to think Lester might want to finish 2014 with a contender, and to have his market improved (only very marginally for a guy like him) by not having draft compensation associated.
 
I personally won't be shocked if this happens.  Every step of it makes sense to me.  The whole thing in combination makes for an unusual story, but so what?  I think it makes sense for Lester and the Sox if Lester gets traded.  I think if I'm Ben and I have approval to pay Lester what it takes to extend him right now, I would also be willing to pay a few extra million to sign him as a FA.  Lester should be happy because he gets to come back to Boston and gets essentially full market value.  Ben gets a significant prospect package, an improved draft position next year, and a few extra months to make sure nothing tragic happens to Lester's career before this giant new contract becomes official.  Ben loses, say, a 2-3 million a year over the life of the new deal (Does anyone have a good way to estimate that extra price?) and the exceedingly small chance that Lester would be enough to change the 2014 Sox playoff standing.
 
The only piece about this whole situation that could have made it a terrible idea would be if Lester took the position that trading him is an insult.  I think we now have sufficient evidence that's not the case.
Has this ever happened with a top free agent? I can't think of a single example. I also struggle to see the Sox paying him full market value, don't think Lester gives any discount to the Red Sox, and think a team that's willing to give up the best prospect package is likely to be a team that wants Lester after 2014.

I'd give 15-1 odds for a jimmy fund bet against him signing as a FA here if he's traded.
 

ivanvamp

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Goodness, could Lester be playing this any more perfectly?  He has stated all along he wants to stay here.  He's adamant.  Hometown discount and all.  Then it gets leaked (by whom?  haha) that he was offered just 4/70, but he makes no public statement about it at all.  No sign of bitterness.  No sign of insult.  Just reiterates that he wants to be here.  His camp expresses that he'd have taken Homer Bailey money.  Which, as the market unfolds, IS a heck of a hometown discount.  He stays the course.  Pitches his rear end off, having the best season of his career.  Trade rumors swirl.  Sox don't offer another deal.  Larry says no negotiations until the season is over.  Hamels is mentioned.  Lee is mentioned.  Lester then says, yeah, if I'm traded, I'd love to come back to Boston, and I understand that the Sox need to do what's best.  
 
I mean, good grief.  He's handling this as well as any player I've ever seen.  It would be amazing to trade him and get back a top prospect (Pederson, etc.) and then re-sign him, even at big money, in the offseason.  I don't think that happens, but there is NO FREAKING WAY he can be vilified on the way out, can he?  No way.  Not the way he's been pitching, his stellar postseason record, his overcoming cancer, and the way he's handled all this.  No way.
 

dcmissle

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Snodgrass'Muff said:
It would bee stupid for Lester's camp to eliminate the Red Sox as a destination publicly as it would be one less big market team to drive up the price and one less division rival to push the Yankees with. Even if he's not interested in coming back I'm guessing they will keep having conversations with Ben to keep up pretenses.

Even still, that's comforting to read and makes me feel better about trading him.
Yes. Something else that would be stupid -- the RS not making a full offer for Lester, unless they don't want him plain and simple.

I don't think there will a lack of suitors, but there is one thing worse than Lester in pinstripes. It's Lester in pinstripes at a price that leads you to shake you head and say, that's fair to both sides; not an overpay at all
 

ivanvamp

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It is still possible that Lester would take a hometown discount of sorts to play for Boston.  So if NY offered 6/160 and Boston offered 6/145, it's possible that 6/145 gets it done for Boston.  But NY probably would just push the cost out of the stratosphere.  They have a desperate need, and they have the resources.  Usually when that happens, they get what they want.
 

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bosockboy said:
If he is traded and gets to FA, zero chance we outbid the Yankees. They'd outbid us just for sport.
I agree.

Cashman presumably could have cut out the Tigers and traded Ian Kennedy for Scherzer a few years ago. Perhaps I'm reading too much into his decision to do a 3-way deal, but if you assume Cashman was as surprised as anyone by Granderson's terrific performance after the trade, I don't see how he doesn't take Scherzer instead unless he shared Arizona's concerns about his durability. Maybe those concerns are less pronounced now, but having formed that opinion at one time, I would be surprised if Cashman fell over himself to guarantee $150mm or more to Scherzer when an alternate target of Lester's quality is available (and would allow him to tweak the Red Sox, for whatever that's worth).
 

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Cashman may be down his lefty ace (forever) and Tanaka next year, Kuroda is a FA, and who knows about Pineda,  so depending on what the budget is, they may have an appetite for both Lester and Scherzer. If I were to prioritze I'd think Lester as he's a LH and pitches well in the Urinal.
 
dcmissle said:
Yes. Something else that would be stupid -- the RS not making a full offer for Lester, unless they don't want him plain and simple.

I don't think there will a lack of suitors, but there is one thing worse than Lester in pinstripes. It's Lester in pinstripes at a price that leads you to shake you head and say, that's fair to both sides; not an overpay at all
 Re the bolded, IMO if (probably when) Lester signs a FA contract it will be a huge but defendable market-based contract, but this soap opera could have been avoided if certain 30+ beliefs had not became dogma, and somebody felt they had to "win" the negotiation, by trying to leverage Lester's loyalty.
 

Granite Sox

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Idabomb333 said:
The only piece about this whole situation that could have made it a terrible idea would be if Lester took the position that trading him is an insult.  I think we now have sufficient evidence that's not the case.
 
Trading him may, in fact, be a very big insult.  These quotes are for public consumption and are part of a carefully scripted message designed to maximize Lester's value.  He's performed very well this year, and his public comments have been pitch-perfect (pun intended) for the Boston market.
 
While true that Boston/The Red Sox are all he's ever known, trading him provides him the opportunity to acclimate to what a change in franchises would be like for him and his family.  But he may also view a trade as the final nail in his Boston coffin.  We don't really know (and may never until the FOSC*).
 
The optimal outcome would be to trade him, and then re-sign him at the end of the season.  I don't think the FO is willing to make that open-market financial commitment even if it received a couple of prospects in return.  The worst possible outcome is the path this appears to be heading down... August and September as the Lester Farewell Tour, then a decampment to New York for big bucks, with no substantive return for the Sox.
 
I'm resigned to the fact he won't be re-signed... trade him and maximize the return.
 
 
 
*FOSC = Front Office Smear Campaign
 

bosockboy

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Steering him towards the Dodgers who would have a higher likelihood of resigning him is the best case scenario. Try and control his long term destination.
 

dcmissle

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ivanvamp said:
Goodness, could Lester be playing this any more perfectly?  He has stated all along he wants to stay here.  He's adamant.  Hometown discount and all.  Then it gets leaked (by whom?  haha) that he was offered just 4/70, but he makes no public statement about it at all.  No sign of bitterness.  No sign of insult.  Just reiterates that he wants to be here.  His camp expresses that he'd have taken Homer Bailey money.  Which, as the market unfolds, IS a heck of a hometown discount.  He stays the course.  Pitches his rear end off, having the best season of his career.  Trade rumors swirl.  Sox don't offer another deal.  Larry says no negotiations until the season is over.  Hamels is mentioned.  Lee is mentioned.  Lester then says, yeah, if I'm traded, I'd love to come back to Boston, and I understand that the Sox need to do what's best.  
 
I mean, good grief.  He's handling this as well as any player I've ever seen.  It would be amazing to trade him and get back a top prospect (Pederson, etc.) and then re-sign him, even at big money, in the offseason.  I don't think that happens, but there is NO FREAKING WAY he can be vilified on the way out, can he?  No way.  Not the way he's been pitching, his stellar postseason record, his overcoming cancer, and the way he's handled all this.  No way.
Lester has been a maestro.

He has just announced to the world that the RS can make the team stronger, and not compromise re-signing him.

Whether this proves true or not, this IS a concession. Being dealt at the deadline is a pain-in-the-ass. The criticisms of players who don't welcome it -- "oh, he is not a competitor and so forth" -- most often voiced by talking heads who have never played, are fanboy bullshit. Particularly when you're talking about a guy who already has two rings.

The road the next week is not rocket science. The RS should identify teams (a) for which Lester would be a difference makes and (b) that have prospects we want. Then you call those teams and tell them that Lester is available at the right price (not any price), and if there is more than one that's interested, you play them off against each other.

It is that simple, and you can bet that our FO has at its disposal teams that fit categories a and b above.

If they fail to improve the club, it's on them or ridiculous trading partners, not on Lester.

The move now -- and it has been the obvious move for at least a week -- is for the RS to make the max effort to extend Lester and find his real number. If he does not cooperate in that, you know there will be no hometown discount of any sort, and that he's gone for good.
 

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dcmissle said:
The move now -- and it has been the obvious move for at least a week -- is for the RS to make the max effort to extend Lester and find his real number. If he does not cooperate in that, you know there will be no hometown discount of any sort, and that he's gone for good.
I don't think this is necessarily true.  Lester is missing an important piece of information right now--that is, just how much will he fetch on the open market?  Is Verlander going to be the template for a deal or a cautionary tale?
 
If Scherzer gauged the market correctly in walking away from 6/144, and both he and Lester get offers in the Verlander zone, then yeah, he's almost certainly gone.  But what if the offers don't get much better than Greinke? Then something like 5/120 with a vesting option for a sixth year might be good enough for Lester, not because he wants to give the FO a break but because he thinks it's the best option for his family and he's not walking away from an obscene amount of money.
 

CYaz

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If the Sox can trade Lester for a prospect who can be an above average outfielder for the next six years at cost controlled prices, they may consider re-investing some of those " savings" (as opposed to extending Victorino or signing a similar player) into re-signing Lester.

So, if the Sox can play, say, Joc Pederson or Tavares for the next six years for a total cost of $25-$40 million, that would be a savings (compared to a Victrino-like signing for 6 years at $14 m per, or $84 m) of around $50 m. If the Sox attribute some of those dollars to Lester (as the cost for not re-signing him in the offseason), then even a 6/$150 deal looks like a good deal for both sides.

Of course, that assumes the Sox can identify and get a prospect in a position of need (eg, RF) who will give the Sox six years of above average production.

I would use a similar analysis for Uehara. After all, neither of Lester nor Uehara will require a comp pick to re-sign.

And past cases aren't all a great comp. the Sox won't be trading Lester bc they can't afford him, unlike many past trades of players who then don't re-sign.
 

LeoCarrillo

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How out of the realm of possibilities is it for Ben to approach Lester's agent and say, ok, we'll meet your demands in FA on years and cash -- if you go along with us this week and take a two-month stint for the Dodgers for stud prospects?

Then you get paid, everyone's happy, and the team you return to this winter is even better with Joc Pederson or whoever on the 40 man.
 

Yaz4Ever

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LeoCarrillo said:
How out of the realm of possibilities is it for Ben to approach Lester's agent and say, ok, we'll meet your demands in FA on years and cash -- if you go along with us this week and take a two-month stint for the Dodgers for stud prospects?

Then you get paid, everyone's happy, and the team you return to this winter is even better with Joc Pederson or whoever on the 40 man.
Not out of the realm of possibilities.  However, if they were caught doing this I'd imagine there would be ramifications.  Big ones.
 
Also, if that's truly Ben's approach (I'd love it to be true if Lester has already signed off on it and keeps his word) isn't it a dangerous move?  
 
Agreement in place.  Check.  
Trade for uber prospect(s).  Check.  
Acquire Stanton or in some other way make Sox better for next year.  Check.  
Get Lester's signature on new contract.  <ring ring>Hey, Jon.  This is Brian Cashman.  I'd like to sign you for 6 years, $180M.  Check?
 

Paradigm

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I was thinking about a somewhat similar situation recently with Mets 2B Daniel Murphy:
  • He has very little value to them for the rest of 2014.
  • He could be very valuable to a team competing for the playoffs
  • The Mets would love him back for the 2015 season
If only some kind of trade could be agreed where the Mets sent him to, say, the Giants for some kind of A-ball relief prospect, and the Giants sent him back to the Mets for a non-prospect in the offseason. That would work for both parties!
 

URI

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Since neither the Sox nor Lester are actively pursuing this extension. I'm locking this up. Start a new thread if you want to talk about trading him.
 
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