Extending Lester

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dcmissle

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Both of them also were driven like mules, Sabathia ridiculously so.
 

TheoShmeo

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Harry Hooper said:
 
 
Yes, the same point I made about Speier's column back in January.
Then again, Gammons has been thought of as a Sox mouthpiece (especially for Theo) for years, while Speier appears to be much more of a straight shooter.  Not everyone is a Heyman or Gammons....
 
But to the main point, Gammo's comment fits with what I think is happening all around: The Sox know what Lester wants and aren't prepared to meet it, and Lester either realizes that or has soured on returning based on how negotiations have gone thus far.
 

jimbobim

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bankshot1 said:
The concern should be that Gammons may be floating the Sox rationale for letting Lester walk 200 miles down the road.
 
Bingo. 
 
Still as I explained more above I think the rationale is flawed because it views signing Lester in a vacuum and doesn't account for the realities of the baseball market this offseason and the foreseeable future. Lester is producing at an insane rate this year. Someone is going to have to pitch those innings next year. If they don't want to pay Lester they probably won't be competitive on Shields Sherzer etc .
 
Even if you get better then expected production from Owens De La Rosa Workman Webster Renaudo the rotation adds up to Lackey Clay and then three spots for the young guns and doubrount if he's still around.
 
If that is the "plan" they better be spending big on offensive support maybe Hanley at 3b . Still ugg...   
 

dcmissle

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This isn't that complicated. We may think it is, but only because our Boston Red have typically approached these situations with the emotional maturity of a 12 year old boy.

We either are in the ballpark, or we aren't. You find that out by calling his agent. Agents will always talk to you. You keep this off the air waves and internet, and out of the fucking papers.

If the agent won't engage, then you calmly explain that you have a fiduciary responsibility to test the trade market for Lester. He may not like that; contrary to fanboy expectations, lots of players don't like to be uprooted at the end of July. But he is not going to be a drama queen about it. To maximize his FA value, he has to be professional and produce.

If this is the direction it goes, you calmly explain your rationale to the fan after the fact. We don't want to invest in a 30 year old to the tune of 6 years and 150 million. We may be right, or we may be wrong, but we have a different vision. Yes, we are taking a risk. We thank Jon Lester for his long and faithful service. He will always be a Red Sox in out hearts.

Done. The same classy and professional way the Cardinals parted with Pujols, absent the trade

I know we're sadly addicted to the spectacle of the other way this team has done its business, but it's time to move on from that.

They did it with Ellsbury, and they can do it with Lester if need be, even though this is a more difficult situation.
 

Hoplite

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Theoretically, let's say Lester could be extended for 6 years/$150 million. And theoretically, let's say that we could trade Lester for a top 50 prospect, open up a rotation spot for one of our prospects to audition, and get a top three draft pick next year. What would the majority of fans here prefer?
 

MakMan44

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Hoplite said:
Theoretically, let's say Lester could be extended for 6 years/$150 million. And theoretically, let's say that we could trade Lester for a top 50 prospect, open up a rotation spot for one of our prospects to audition, and get a top three draft pick next year. What would the majority of fans here prefer?
Probably the extension. I don't like having to go to 6 years, I'd prefer to keep it to 5 but Lester has been really good for a while and there's no guarantee that any of the prospect (even the newly acquired top 50 one) will pan out to the degree Lester has. 
 

Minneapolis Millers

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Depends on the prospect.  Joc Pederson, who would fill an organizational gap/need?  Probably the prospect.  I want them to resign Lester, but there are limits, and 6/150 is a year and about $3M per too far for me.
 

amfox1

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Hoplite said:
Theoretically, let's say Lester could be extended for 6 years/$150 million. And theoretically, let's say that we could trade Lester for a top 50 prospect, open up a rotation spot for one of our prospects to audition, and get a top three draft pick next year. What would the majority of fans here prefer?
 
Under your scenario, I trade Lester and it's not close.  A top 3 pick and a top 50 prospect are essentially two good major leaguers.  
 
Two of the top three 2013 draftees are top 10 prospects a year later (the third is Appel).  Two of the top three 2012 draftees are top 10 prospects and the third (Zunino) is in the majors.
 
If we cannot sign Lester, we'll get a pick between 28 and 35 and nothing else.  Personally, my limit on Lester is 5/$110.
 

MakMan44

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Okay, but why does trading Lester guarantee a top 3 pick? The Sox are only something like 4 games away from being the worst team in baseball WITH Lester. Trading Lester obviously makes them worse, but it wouldn't be the straw that breaks the camel's back. 
 

bankshot1

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Francesa, when informed by a listener, that Lester is 30 and likely a FA next year, sagely informed his audience he'd (the MFY) would give him a 2-year deal for "big-money"
 
Why do i listen to him?
 

glennhoffmania

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Can I assume that the people who want to limit the deal to something like 5/110 think that Lester is going to fall off a cliff in the middle of the contract?  Because even if we use $6m per win for the next 5 years and totally ignore inflation, that's 18.3 wins or 3.7 per year.  Lester has averaged 4.6 wins per year (using FG) since 2008, ignoring 2014 YTD.  Taking into account the facts that inflation exists, you generally pay a premium for top FAs, and if he walks there's a good chance NY gives him 7/175, why are people drawing an imaginary line in the sane at 5/110?  If something like 6/140 could get this done right now and the FO thinks saving 30m over the next 6 years is worth losing him to NY then that seems incredibly penny wise, pound foolish to me.
 

Super Nomario

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amfox1 said:
 
Under your scenario, I trade Lester and it's not close.  A top 3 pick and a top 50 prospect are essentially two good major leaguers.  
Both of these are a 50/50 chance at a good major leaguer, and I'd be surprised if it's even that high. Look at the success rate of top three picks over the last 10 years - there are a lot of guys like Donavan Tate and Dustin Ackley (2009), Tim Beckham (2008), Josh Vitters (2007), Luke Hochevar and Greg Reynolds (2006), Jeff Clement (2005), Matt Bush and Phil Humber (2004), Kyle Sleeth (2003), Bryan Bullington and Chris Gruler (2002). There are a lot of busts, and very few players that make it to Lester's level.
 

Hoplite

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MakMan44 said:
Okay, but why does trading Lester guarantee a top 3 pick? The Sox are only something like 4 games away from being the worst team in baseball WITH Lester. Trading Lester obviously makes them worse, but it wouldn't be the straw that breaks the camel's back. 
 
Trading Lester could be the difference between a top 5 pick and the top pick in the draft. Lester pitching for a contract and us trying to get the best possible draft pick aren't compatible.
 

MakMan44

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Hoplite said:
 
Trading Lester could be the difference between a top 5 pick and the top pick in the draft. Lester pitching for a contract and us trying to get the best possible draft pick aren't compatible.
Lester is 9-7 right now and the team is 11-7 in his starts. That's not a huge swing on the overall record. 
 
I mean, the team is 5-13 in Peavy's starts and he's 1-7 but you don't see people suggesting that we keep him around to tank harder. 
 

Hoplite

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glennhoffmania said:
Can I assume that the people who want to limit the deal to something like 5/110 think that Lester is going to fall off a cliff in the middle of the contract?  Because even if we use $6m per win for the next 5 years and totally ignore inflation, that's 18.3 wins or 3.7 per year.  Lester has averaged 4.6 wins per year (using FG) since 2008, ignoring 2014 YTD.  Taking into account the facts that inflation exists, you generally pay a premium for top FAs, and if he walks there's a good chance NY gives him 7/175, why are people drawing an imaginary line in the sane at 5/110?  If something like 6/140 could get this done right now and the FO thinks saving 30m over the next 6 years is worth losing him to NY then that seems incredibly penny wise, pound foolish to me.
 
The -0.5 WAR per year that most projection systems figure in for decline over the age of 30 far outweighs inflation.
 

Hoplite

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MakMan44 said:
Lester is 9-7 right now and the team is 11-7 in his starts. That's not a huge swing on the overall record. 
 
It's a .611 WPCT in Lester starts versus a .394 WPCT in non-Lester starts. I'd say that's fairly significant considering there are currently five teams with worse records than us.
 

MakMan44

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Hoplite said:
 
It's a .611 WPCT in Lester starts versus a .394 WPCT in non-Lester starts. I'd say that's fairly significant considering there are currently five teams with worse records than us.
That's a fair point. 
 
I suppose I just think that the suggestion that they should trade Lester to move up in the reverse standings is a very silly one. 
 

glennhoffmania

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Hoplite said:
 
The -0.5 WAR per year that most projection systems figure in for decline over the age of 30 far outweighs inflation.
 
There are plenty of pitchers who didn't decline by a 1/2 win per year starting at age 30.  That isn't to suggest that Lester won't decline during the course of the contract but that rate of decline is hardly a given.  Then when you factor in inflation, the premium that will be required for a top FA deal, and the loss of a really good pitcher to a direct competitor and I really don't see how a deal in this general range is so offensive.
 
At some point the FO has to decide if they're simply done paying market rates for top pitching.  This is what it costs right now.  If they're uncomfortable with any deal that involves taking on some risk in years 4, 5 or 6 then they better be extremely confident in their ability to keep churning out top pitching prospects.
 

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Hoplite said:
 
It's a .611 WPCT in Lester starts versus a .394 WPCT in non-Lester starts. I'd say that's fairly significant considering there are currently five teams with worse records than us.
 
I honestly wouldn't mind a complete punt of the remaining season to get the younger players experience at this point.   If we get a high pick due to a last place finish, so be it.  
 
I don't think we'd finish dead last though, even if we traded Lester, promoted Vasquez and let all the younger players figure things out as they go.   
 

Hoplite

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MakMan44 said:
That's a fair point. 
 
I suppose I just think that the suggestion that they should trade Lester to move up in the reverse standings is a very silly one. 
 
The $150 million or whatever Lester would require, and the return we could get for Lester in a trade would be the primary motivations not to extend him. Draft position is at best a third consideration, but it is a factor.
 

Snodgrass'Muff

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Hoplite said:
Theoretically, let's say Lester could be extended for 6 years/$150 million. And theoretically, let's say that we could trade Lester for a top 50 prospect, open up a rotation spot for one of our prospects to audition, and get a top three draft pick next year. What would the majority of fans here prefer?
 
 
Hoplite said:
 
Trading Lester could be the difference between a top 5 pick and the top pick in the draft. Lester pitching for a contract and us trying to get the best possible draft pick aren't compatible.
 
Then the choice should be between extending Lester for 6 years at 150 or whatever plus a pick in the 5-7 range versus trading him for a top 50 prospect and a pick in the 1-4 range.  Dangling the pick on the "trade" side of the question is stacking the deck  to try and illicit responses favorable to your position.  The third option is letting him turn down a QO to generate a pick in the compensation round and also likely picking in the 5-7 range.
 
If I had to choose out of the modified version of the question, I pick extending Lester and drafting in the 5-7 range.  The chances that a top 4 pick turn into Jon Lester over the next 5 years are still pretty slim.  Same for a top 50 prospect.  I'd rather have Lester's likely production in the 3-4 WAR a year range and a pick between 5-7 than hope that a pick between 1-4 or a top 50 pick turn into that.  The odds of a 5-7 pick ending up as productive in the next 5 years as a 1-4 pick aren't so terribly different.  I'd rather bet on that gap than the one between 1-4 and Lester.
 
Edit: Keeping Lester and letting him walk after a QO probably means a pick in the 5-7 range, not 1-4.  Fixed that.
 

Plympton91

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Bob Montgomery said:
There is no way that would be the primary reason they'd trade Lester.  But it would probably be a bi-product.
The problem is, if you trade all the veterans and call up a bunch of kids, and then finish last, then that means the kids haven't performed very well. This isn't 2012 where the lineup would consist of a bunch of has-beens and never-will-be's. If they end up going 21-36 or something during August-September 2014, that's a really bad sign for 2015.
 

MakMan44

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Hoplite said:
 
The $150 million or whatever Lester would require, and the return we could get for Lester in a trade would be the primary motivations not to extend him. Draft position is at best a third consideration, but it is a factor.
Bob Montgomery's Helmet Hat said:
There is no way that would be the primary reason they'd trade Lester.  But it would probably be a bi-product.
The only reason I even mentioned it was because of the top 3 prospect examination above. I think both of you are correct though.
 

Smiling Joe Hesketh

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Plympton91 said:
The problem is, if you trade all the veterans and call up a bunch of kids, and then finish last, then that means the kids haven't performed very well. This isn't 2012 where the lineup would consist of a bunch of has-beens and never-will-be's. If they end up going 21-36 or something during August-September 2014, that's a really bad sign for 2015.
 
Oh come on. God forbid you ever think the kids would improve with time. I mean by this line of thought they should have dumped Buchholz for a bag of magic beans after 2008.
 
Young players are going to struggle at times. You have to let them work through it.
 

Hoplite

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glennhoffmania said:
 
There are plenty of pitchers who didn't decline by a 1/2 win per year starting at age 30.  That isn't to suggest that Lester won't decline during the course of the contract but that rate of decline is hardly a given.  Then when you factor in inflation, the premium that will be required for a top FA deal, and the loss of a really good pitcher to a direct competitor and I really don't see how a deal in this general range is so offensive.
 
At some point the FO has to decide if they're simply done paying market rates for top pitching.  This is what it costs right now.  If they're uncomfortable with any deal that involves taking on some risk in years 4, 5 or 6 then they better be extremely confident in their ability to keep churning out top pitching prospects.
 
And there are some years that free agent prices don't inflate, but it doesn't make any sense for teams or fans to project free agent value based on the exception to the rule. If the Red Sox choose not to pay a premium for Lester and/or a premium to prevent him from singing with a competitor they could instead choose to pay free agent prices for a younger starting pitcher, or a pitcher not coming off a career year or they could elect to trade for a pitcher. There's more than one way to skin a cat.
 

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Plympton91 said:
The problem is, if you trade all the veterans and call up a bunch of kids, and then finish last, then that means the kids haven't performed very well. This isn't 2012 where the lineup would consist of a bunch of has-beens and never-will-be's. If they end up going 21-36 or something during August-September 2014, that's a really bad sign for 2015.
 
You can't worry about that, though. You have to move forward. If they decide that they won't pay what Lester could get elsewhere, AND they believe that Lester won't take a discount, you have to see what kind of package is out there for him. It appears this is an open season on the title, so more teams might be willing to take a shot at it than usual.
 
I keep going back to the Pirates, but they are a case in point. They just shut down Cole again today; if they want to take a real shot at the NLC, they need a pitcher. The Mariners might want a third arm to do battle with the Angels. The Braves could look to bring him on board. Heck, what could you get from the Cards.
 
The price would be less than what the A's paid, because of the free agency; but to the right team at the right time, you might get more than you would expect. 
 

Plympton91

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Smiling Joe Hesketh said:
 
Oh come on. God forbid you ever think the kids would improve with time. I mean by this line of thought they should have dumped Buchholz for a bag of magic beans after 2008.
 
Young players are going to struggle at times. You have to let them work through it.
I didn't say anything about their ability to "improve with time," I said it doesn't bode well for 2015. I think they've got a lot of talent in the minors, but as we've seen with Bogaerts this year, and as you say, you have to let them work through it. If they ditch the whole lot of people being tossed around in the Trading Chips thread and go the Marlins/Pirates/Royals route they should be decent again in 2016, and potentially really good in 2017 to 2019. In which case, I hope they like a lot of empty seats and low NESN ratings for the next 20 months.
 

glennhoffmania

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Hoplite said:
 
And there are some years that free agent prices don't inflate, but it doesn't make any sense for teams or fans to project free agent value based on the exception to the rule. If the Red Sox choose not to pay a premium for Lester and/or a premium to prevent him from singing with a competitor they could instead choose to pay free agent prices for a younger starting pitcher, or a pitcher not coming off a career year or they could elect to trade for a pitcher. There's more than one way to skin a cat.
 
Going by memory, every recent contract for a top starting pitcher has been more than the last one.  Trying to time the market when it may not be going up is not the best way to run a team, especially one with the resources of Boston.  Also, you're assuming that the rule is that a pitcher will decline by 2.5 wins between ages 30 and 34.  I'm not at all being snarky but do you have any numbers to back that up?  Because it sounds very pessimistic to me.
 
Who is this younger and really good FA pitcher they could sign?  Who is the equivalent pitcher they could trade for where the cost in prospects would be less than the cost of Lester's contract? 
 

Hoplite

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Snodgrass'Muff said:
 
 
 
Then the choice should be between extending Lester for 6 years at 150 or whatever plus a pick in the 5-7 range versus trading him for a top 50 prospect and a pick in the 1-4 range.  Dangling the pick on the "trade" side of the question is stacking the deck  to try and illicit responses favorable to your position.  The third option is letting him turn down a QO to generate a pick in the compensation round and also likely picking in the 5-7 range.
 
If I had to choose out of the modified version of the question, I pick extending Lester and drafting in the 5-7 range.  The chances that a top 4 pick turn into Jon Lester over the next 5 years are still pretty slim.  Same for a top 50 prospect.  I'd rather have Lester's likely production in the 3-4 WAR a year range and a pick between 5-7 than hope that a pick between 1-4 or a top 50 pick turn into that.  The odds of a 5-7 pick ending up as productive in the next 5 years as a 1-4 pick aren't so terribly different.  I'd rather bet on that gap than the one between 1-4 and Lester.
 
Edit: Keeping Lester and letting him walk after a QO probably means a pick in the 5-7 range, not 1-4.  Fixed that.
 
Not trading Lester for a top 50 prospect or a useful future major league player and potentially hurting our draft position just to get a compensation round pick for him by offering him a QO would be a major miscalculation. 
 

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Plympton91 said:
I didn't say anything about their ability to "improve with time," I said it doesn't bode well for 2015. I think they've got a lot of talent in the minors, but as we've seen with Bogaerts this year, and as you say, you have to let them work through it. If they ditch the whole lot of people being tossed around in the Trading Chips thread and go the Marlins/Pirates/Royals route they should be decent again in 2016, and potentially really good in 2017 to 2019. In which case, I hope they like a lot of empty seats and low NESN ratings for the next 20 months.
 
I do not agree that if they call up a bunch of kids and the team struggles for the rest of 2014 that automatically means 2015 is a lost cause. They JUST WENT from worst to first in 2013, it's hardly unprecedented for the team to rebound from a bad season and be good again in 2015.
 
And yeah, if they struggle then attendance and TV ratings will fall. Duh. We already know you won't be watching.
 

Snodgrass'Muff

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Hoplite said:
 
Not trading Lester for a top 50 prospect or a useful future major league player and potentially hurting our draft position just to get a compensation round pick for him by offering him a QO would be a major miscalculation. 
 
Based on what?  Do you really think that a 1-4 range pick and/or a top 50 prospect is likely to become what we already have in Jon Lester quickly enough to approximate his value over the life of his next contract?  We're talking about one of those two players accumulating 15-20 WAR over the next five years.  Hell, even betting on both of them combining for that much is very optimistic.  There's a pretty good chance that even if the the 1-4 pick works out, he doesn't even make the majors in the first 4 years of that span.  The top 50 prospect might, but chances are they will struggle early so matching that WAR total is almost certainly not going to happen.  Betting against that seems insanely optimistic to me.
 
Sure the prospects have value beyond that window, but this team is stacking up to be a contender for the bulk of the next 5 years.  Adding a piece or two that aren't likely to contribute to that for at least half of that span at the expense of re-signing a pitcher that does doesn't make sense to me.  Sure, that's a lot of money, but the Red Sox are as well suited to take on a big contract as they've been in a long time.
 

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Super Nomario said:
Both of these are a 50/50 chance at a good major leaguer, and I'd be surprised if it's even that high. Look at the success rate of top three picks over the last 10 years - there are a lot of guys like Donavan Tate and Dustin Ackley (2009), Tim Beckham (2008), Josh Vitters (2007), Luke Hochevar and Greg Reynolds (2006), Jeff Clement (2005), Matt Bush and Phil Humber (2004), Kyle Sleeth (2003), Bryan Bullington and Chris Gruler (2002). There are a lot of busts, and very few players that make it to Lester's level.
 
Some of this is false promise, below-slot deals, injuries and whatnot.  
 
Strasburg, Alvarez, Hosmer, Harper, Machado, Cole, Bauer, Price, Longoria all came out of 2006-2011 drafts.   The hit rate isn't 100 percent, but for a competent team (yes, I'm looking at you TB and SD) it's pretty darn good.  
 

Hoplite

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glennhoffmania said:
 
Going by memory, every recent contract for a top starting pitcher has been more than the last one.  Trying to time the market when it may not be going up is not the best way to run a team, especially one with the resources of Boston.  Also, you're assuming that the rule is that a pitcher will decline by 2.5 wins between ages 30 and 34.  I'm not at all being snarky but do you have any numbers to back that up?  Because it sounds very pessimistic to me.
 
Who is this younger and really good FA pitcher they could sign?  Who is the equivalent pitcher they could trade for where the cost in prospects would be less than the cost of Lester's contract? 
 
For years the general rule of thumb for projecting free agent pitcher contracts ages 31+ has been 5% inflation per year and -0.5 WAR per year. It's referenced all over the place, I just did a google search and found this on fangraphs:
 
 
 
A basic model that has proven to be fairly accurate is to essentially assume a decline of 0.5 WAR per season and 5% inflation in the dollar per win rate each year. 
 
http://www.fangraphs.com/blogs/linear-dollars-per-win-again/
 

Hoplite

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Snodgrass'Muff said:
 
Based on what?  Do you really think that a 1-4 range pick and/or a top 50 prospect is likely to become what we already have in Jon Lester quickly enough to approximate his value over the life of his next contract?  We're talking about one of those two players accumulating 15-20 WAR over the next five years.  Hell, even betting on both of them combining for that much is very optimistic.  There's a pretty good chance that even if the the 1-4 pick works out, he doesn't even make the majors in the first 4 years of that span.  The top 50 prospect might, but chances are they will struggle early so matching that WAR total is almost certainly not going to happen.  Betting against that seems insanely optimistic to me.
 
Sure the prospects have value beyond that window, but this team is stacking up to be a contender for the bulk of the next 5 years.  Adding a piece or two that aren't likely to contribute to that for at least half of that span at the expense of re-signing a pitcher that does doesn't make sense to me.  Sure, that's a lot of money, but the Red Sox are as well suited to take on a big contract as they've been in a long time.
 
That's a pretty weak false dilemma. We'd potentially get the 1-4 overall pick, a top 50 prospect AND $150 million to spend on other free agents/players we trade for. I don't see how you could possibly argue that giving up the chance to trade for a potential top 50 pick, likely hurting our draft position and instead getting a compensation draft pick wouldn't be a loss. Not trading Lester and then not re-signing him would be the worst case scenario.
 

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Hoplite said:
 
Not trading Lester for a top 50 prospect or a useful future major league player and potentially hurting our draft position just to get a compensation round pick for him by offering him a QO would be a major miscalculation. 
 
This begs the question of why Lester wouldn't be traded.  I don't think there is a plan to not trade Lester, and not even try to sign him, because they covet the precious compensation pick.  A fairer assumption would be that, if they do not trade Lester, it is because they are still trying to work out a contract with him.  You can't take two possible outcomes of the situation and arbitrarily claim that the FO is choosing between them with no other considerations.
 

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Hoplite said:
 
That's a pretty weak false dilemma. We'd potentially get the 1-4 overall pick, a top 50 prospect AND $150 million to spend on other free agents/players we trade for. I don't see how you could possibly argue that giving up the chance to trade for a potential top 50 pick, likely hurting our draft position and instead getting a compensation draft pick wouldn't be a loss. Not trading Lester and then not re-signing him would be the worst case scenario.
 
 
It's not a false dilemma.  The Red Sox should be making moves with the goal of putting players who contribute to wins on the major league roster.  Stocking up on draft picks and prospects is great.  I'm a big fan of that.  But at some point you have to invest in veterans.  You simply cannot win without doing so.
 
I agree that not trading him and not re-signing him is the worst case scenario.  That's not a question.  The problem here is that in choosing to trade him and free up that money, you are walking away from that production and then in the position of having to replace it.  You are hoping that you make the right choices to turn those assets into what you would have gotten from Lester (or hopefully more).  There is a very real chance you come up short, though.
 
If they were likely to be withing 30 million of the cap going into the winter (or less), then trading Lester would make more sense to me.  They aren't going to be strapped for cash, though.  They need to focus on making good bets with the resources they have, and they have a good bet on the roster right now saying he wants to stay.  Make the safe bet while you can.  They're going to spend that money.  I don't see a good reason it shouldn't be on Lester.  A top 50 prospect and a draft pick 3-4 spots higher doesn't compel me to change my mind.
 

Drek717

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E5 Yaz said:
 
You can't worry about that, though. You have to move forward. If they decide that they won't pay what Lester could get elsewhere, AND they believe that Lester won't take a discount, you have to see what kind of package is out there for him. It appears this is an open season on the title, so more teams might be willing to take a shot at it than usual.
 
I keep going back to the Pirates, but they are a case in point. They just shut down Cole again today; if they want to take a real shot at the NLC, they need a pitcher. The Mariners might want a third arm to do battle with the Angels. The Braves could look to bring him on board. Heck, what could you get from the Cards.
 
The price would be less than what the A's paid, because of the free agency; but to the right team at the right time, you might get more than you would expect. 
A deal sending Peavy to the Cardinals followed by a deal sending Lester to the Pirates would have a very interesting impact on the NL Central race.
 
Something like Peavy for Craig, then Lester for Tyler Glasnow, Josh Bell,and Andrew Lambo.  Glasnow adds a long term developmental pitcher, Bell is a long term 1B/DH/LF play.  Lambo is a bat to throw in the mix for 2015.
 

Hoplite

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Oct 26, 2013
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Snodgrass'Muff said:
 
 
It's not a false dilemma.  The Red Sox should be making moves with the goal of putting players who contribute to wins on the major league roster.  Stocking up on draft picks and prospects is great.  I'm a big fan of that.  But at some point you have to invest in veterans.  You simply cannot win without doing so.
 
I agree that not trading him and not re-signing him is the worst case scenario.  That's not a question.  The problem here is that in choosing to trade him and free up that money, you are walking away from that production and then in the position of having to replace it.  You are hoping that you make the right choices to turn those assets into what you would have gotten from Lester (or hopefully more).  There is a very real chance you come up short, though.
 
If they were likely to be withing 30 million of the cap going into the winter (or less), then trading Lester would make more sense to me.  They aren't going to be strapped for cash, though.  They need to focus on making good bets with the resources they have, and they have a good bet on the roster right now saying he wants to stay.  Make the safe bet while you can.  They're going to spend that money.  I don't see a good reason it shouldn't be on Lester.  A top 50 prospect and a draft pick 3-4 spots higher doesn't compel me to change my mind.
 
I agree that we need to sign veterans who will contribute to wins in 2015, and that's exactly what we'd do with the $150 million we don't spend on Lester if we don't re-sign him. Even with our financial flexibility next year, we're not going to have trouble spending the money. Plus, we could potentially get a higher draft pick in 2015 and the return from the Lester trade. It could be a win-win for now and the future because I'm not convinced that signing a 30 year old starting pitcher coming off a career year to a roughly market value contract would be the best uses of our financial resources. And trading Lester would unquestionably give us greater prospect resources to keep or trade for more veterans who could contribute to wins.
 

Super Nomario

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amfox1 said:
 
Some of this is false promise, below-slot deals, injuries and whatnot.  
 
Strasburg, Alvarez, Hosmer, Harper, Machado, Cole, Bauer, Price, Longoria all came out of 2006-2011 drafts.   The hit rate isn't 100 percent, but for a competent team (yes, I'm looking at you TB and SD) it's pretty darn good.  
Any team can whiff on the draft - as an exercise in predicting the future, it's an imperfect science at best. And not all the guys you mentioned are success stories yet - Hosmer's having a ghastly year, Bauer's been nothing special so far, Alvarez has been spotty, even Harper and Machado have just been OK so far. It's also worth noting that Strasburg, Harper, Cole, and Price were #1 picks - if I'm getting the #1 pick, that's more valuable than just a "top 3" pick.
 

snowmanny

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Hoplite said:
 
I agree that we need to sign veterans who will contribute to wins in 2015, and that's exactly what we'd do with the $150 million we don't spend on Lester if we don't re-sign him. Even with our financial flexibility next year, we're not going to
have trouble spending the money. Plus, we could potentially get a higher draft pick in 2015 and the return from the Lester trade. It could be a win-win for now and the future because I'm not convinced that signing a 30 year old starting pitcher coming off a career year to a roughly market value
contract would be the best uses of our financial resources. And trading Lester would unquestionably give us greater prospect
resources to keep or trade for more veterans who could contribute to wins.
In your scenario where the Red Sox spend $150MM dollars on free agents does this cost any draft picks?
 

Hoplite

New Member
Oct 26, 2013
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snowmanny said:
In your scenario where the Red Sox spend $150MM dollars on free agents does this cost any draft picks?
 
Doesn't seem like our front office's style, but even if we do sign a big name free agent who requires a compensation pick we'd still be coming out ahead overall in the prospect department going from a 4-7th overall pick to a 1-3rd overall pick and getting a top 50 prospect in return for a compensation pick. The difference in value between a top 50 prospect already in A-AAA, a compensation pick in the draft and the slot money is like night and day.
 

Snodgrass'Muff

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Mar 11, 2008
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Hoplite said:
 
I agree that we need to sign veterans who will contribute to wins in 2015, and that's exactly what we'd do with the $150 million we don't spend on Lester if we don't re-sign him. Even with our financial flexibility next year, we're not going to have trouble spending the money. Plus, we could potentially get a higher draft pick in 2015 and the return from the Lester trade. It could be a win-win for now and the future because I'm not convinced that signing a 30 year old starting pitcher coming off a career year to a roughly market value contract would be the best uses of our financial resources. And trading Lester would unquestionably give us greater prospect resources to keep or trade for more veterans who could contribute to wins.
 
Cot's has the Sox on the hook for about 75 million next year.  Add in 15 for arbitration and other costs and you're at 90 or so.  That leaves them with about 85 million to spend.  Spending 24 on Lester does not slow down their efforts to fill out the rest of the roster.  In fact, if they don't spend 24 on Lester, chances are they will come in well under the luxury tax limit because the free agent market doesn't have all that much worth spending on in the first place.  Let's break this down quickly starting with the offense, since this is the area most in need of help.
 
Positions they are set at: DH (Ortiz), 1B (Nap), 2B (Pedroia), CF (Bradley and/or Betts), RF (Victorino) and either SS or 3B depending on where Bogaerts ends up.
 
Positions they have assets to plug into already: SS or 3B (Marrero, Middlebrooks, Cecchini), LF (Nava, Betts, Brentz), and Catcher (Vazquez)
 
So we are looking at the front office potentially looking for a free agent catcher, a 3rd baseman and maybe a corner outfielder.
 
Catcher: The best free agent catchers are Russell Martin, Geovany Soto and Kurt Suzuki.  All three could also cost a compensation pick, but none of them should be prohibitively expensive.  If the Sox have a protected pick, they may be willing to give up their second rounder to fill in that gap or maybe they hope a combination of Vazquez and Butler can get them through enough of the season to fast track Swihart.  If they go for a stop gap free agent, it'll probably cost 12-15 million.
 
3rd Base: This market is kind of interesting.  Chase Headley might be worth a make good contract while Cecchini and Marrero spend some time seasoning in The Bucket.  Of course, they could also go big after Hanley Ramirez.  That's probably at least 25 million a year commitment and most certainly a draft pick.
 
Corner OF: Melky Cabrera is an interesting option.  Nelson Cruz stands out as someone who could be productive, but he's old enough that he'd have to be willing to go short on years.  Same with Denofria. After that it gets pretty ugly.  Melky is the most interesting name and he's probably going to cost around 15 a year over 4 or 5 years.  Basically, a JD Drew contract.  His offense is not far off from Drew but he's got the PED suspension hanging from his neck.  He'll cost a draft pick as well.
 
So, even if the team goes against its history and chooses to piss away draft picks to sign one of each, and they go big and sign the best option in each category, you're looking at a total cost of about 55 million a year.  Chances are, they'll draw the line at one sacrificed draft pick if they cross that line at all, so it's more likely they would target the best value and call it a day.  Even if they go with Hanley, that's only 25 million or so a year and a small fraction of what they have free to play with this coming winter.
 
Looking at the starting rotation they have Lackey, Buchholz, Doubront, Workman, Webster, DLR and Ranaudo to build a rotation with if they don't bring Lester back.  Sure, they could have a decent rotation with those guys, but chances are they want a veteran in the rotation they can count on for a while to be the elder statesman while the kids break in.  If it's not Lester they can break the bank for Scherzer.  If they won't pay market rates for Lester, I doubt they do it for Scherzer, though.  They could look for a value deal in someone like Masterson or Gavin Floyd.  Or maybe they take a shot at James Shields.  Masterson or Floyd probably ring in at about 15 a year.  Shields is probably between that an 20 somewhere.
 
Unless you think the team is going to let Lester walk and build their rotation without any free agent help, the team is probably spending between 15 and 20 million a year to do so, and they'll end up with a considerably worse pitcher than Jon Lester for their trouble.  Either way, I don't see Lester's roster spot or his potential AAV getting in the way of spending on any other pieces they might want come December.  I don't think they are likely to go after any of the QO free agents, but they'll have plenty of financial flexibility available if they decide it's worth it.
 
If they're not going to spend a ton on offense anyway, and they will likely need to replace Lester with a veteran, why not spend a little more on a better bet?  I'm just talking about the money they would or wouldn't spend on Lester here.  The team is going to spend most or all of it on a replacement anyway, so why not do it on the kid who has been here his whole career, has expressed a desire to stay, is likely to be better than any of the realistic options to replace him and won't cost them a draft pick to replace?  A top 50 prospect and the difference between 4-7 or 1-3 in the draft doesn't close the gap between Lester and one of Masterson, Floyd or Shields for me.  Especially when you add in the likelihood of having to forfeit a second round pick as part of that move.
 

bankshot1

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Gammons on Francesa: The Sox are now determining which teams can rent/and then sign Lester. He would not rule out Sox/MFY discussions. 
 
IMO its hard to imagine a true win/win in any deal between those two clubs.
 

E5 Yaz

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bankshot1 said:
Gammons on Francesa: The Sox are now determining which teams can rent/and then sign Lester. He would not rule out Sox/MFY discussions. 
 
They would have to think someone who can trade for and then sign him would offer more in a return. Did Gammons get into other teams as possibilities?
 

glennhoffmania

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bankshot1 said:
Gammons on Francesa: The Sox are now determining which teams can rent/and then sign Lester. He would not rule out Sox/MFY discussions. 
 
IMO its hard to imagine a true win/win in any deal between those two clubs.
 
This is truly depressing, and not because it may involve NY.  How much can Lester really be asking for that they'd rather trade him, even if it's within the division, then keep him around for the next 6 years?  If they're not willing to pay market rate for Lester I can't imagine what pitcher they would do it for.  Guys like Felix and Kershaw will never become available in their 20s.
 
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