Extending Lester

[RedOctober3829]

 
Because we don't know what they offered and we don't know what he considers "less money to sign".  Less money than what?  For all we know, "less money" to Lester is $1M a year lower than market, but only if it's for 5+ years.
 
No matter what we keep seeing speculated in the media, we're all flying blind here.  We know nothing, so we're really not in any position to judge one way or the other.

Anything they would have signed him for in February would be less than what it would take in November.  He even said that much so in the winter.  This is a quote from Lester from the Boston Herald in January.
 

"I understand that to stay here you're not going to get a free agent deal. You're not going to do it. You can't. It's not posible," Lester said. "You're bidding against one team. I understsand that you're going to take a discount to stay. Do I want to do that? Absolutely. But just like they want it to be fair for them, I want it to be fair for me and my family. If we can get to something hopefully in spring training, that's awesome.
"As a competitor, you always want to play for a competitive team. I've never been the type of guy that's going to take more money from somebody else to go suck. I don't want to do that. I mean, that's no fun. I want to win, and if that means taking a Pedroia deal where you stay here for less money to be happy and be competitive and win every year, let's do it, lets get it done. (The Red Sox) are my No. 1 priority. I want to be here until they have to rip this jersey off myback. Hopefully we get something done in spring.
 

http://bostonherald.com/sports/red_sox_mlb/clubhouse_insider/2014/01/jon_lester_on_possible_extension_with_red_sox_i_want_to
 
This quote is so spot on in this sense.  He'll take less to stay, but something that is close to fair market value.  If the Red Sox don't want to pay a bit below the market value for an ace and instead want him to take a Pedoria-type deal which is way below market value then they are sorely miscalculating what others will pay for him.  As I said upthread, 5 years/$125 million would be a fair deal for both sides.  Lester gets $25M AAV and a chance to get another contract at 35-36 and the Red Sox don't have to go 6 or 7 years.  Once it gets to free agency, I think the years will go up on this figure and the dollar figure will either stay the same or go up.  Do they get this deal done in the negotiating period in November?  I don't think so as he has taken it this far he might as well go to FA and see what the market opens up for him.

 

[dcmissle]

The last two posts go well together.

Asking for a home town discount is fine, particularly when the player has said he's receptive.

Deciding you'll pay so much and no more, per your own value index, also is fine. Your number may be off with a player like Lester, but in principle there is nothing wrong with drawing your own line.

The road to hell is demanding that discount while confusing what the market is with what you'd like it to be. You can't hard bargain in an unrealistic neighborhood. You're then insulting the guy and it becomes personal. And yes, you can insult someone while offering tens of millions of dollars.

 

[MakMan44]

I just had to check the FA SP list for another post and I really hope the extension gets done.

 

[wade boggs chicken dinner]

 
Because we don't know what they offered and we don't know what he considers "less money to sign".  Less money than what?  For all we know, "less money" to Lester is $1M a year lower than market, but only if it's for 5+ years.
 
No matter what we keep seeing speculated in the media, we're all flying blind here.  We know nothing, so we're really not in any position to judge one way or the other.

 
It's interesting that everyone is focused on what the Sox management have been doing and no one thinks that Lester has any responsibility for this.
 
Yes Lester has said all the right things about "hometown discount," but as RHF said, we don't know where he thinks the discount should be from.  Count me as one of the people who think that Ben started negotiations at 4/$70 but never received a counter.  Why should his agents counter here?  Lester's performance is counter enough.  So if Lester doesn't counter, what does Ben do?  Just keep raising his offer?
 
The issue is that we don't know what Lester would take to sign.  If Lester really wanted to be with the Sox for 5/$100, I'm pretty sure that would have been done months ago.  All he needed to do is say, "I'll take 5/$100"; do people really think that the Sox are going haggle between that and 4/$70? 
 
And if I'm Lester, I have no idea what I would sign for.  Lester is probably being told by the Levinsons that he at minimum will get Tanaka money.  Given how much money is sloshing around baseball, that's probably accurate.  How many people want to sign Lester for $140 million or more? 

 

[EpsteinsGorillaSuit]

In negotiations, the first offer anchors the discussion. That is, if the initial offer from the Red Sox was 4/$70M, they are certainly hoping to end up at 5/$100M or so. There has been a lot of hot air in this thread about those offers being appropriate, but that's an extremely Red Sox-centric view. Neither one are anywhere near Lester's market rate.
 
When faced with an extreme lowball offer, the appropriate negotiation tactic is to NOT make a counter offer. The correct move is to declare the initial offer as an inappropriate starting point for further discussion. That way, the negotiations are not tainted by the initial low anchor, and the counterparty is forced to come back with a more appropriate offer without knowledge of exactly what hometown discount Lester has in mind. Or, as seems to be currently happening, the stalemate increases Lester's leverage over the course of the season.

 

[chrisfont9]

He's not signed when he keeps saying he would've taken less money to sign.  This would be a sign that the FO blew their chance at a "hometown discount".  How is this not a mistake?

I would call it a gamble rather than a mistake. Depending on what sort of season Lester put up, it could have brought his price up or down. Obviously the most recent performance tends to influence the price. Unfortunately for the Sox' negotiating position, he's putting up a strong season and raising his price. That doesn't stop the Sox from being the ones who pay it.
 
The FO's tendency has been to be more shy of the years than the price, no? I think they were holding out hope of getting Lester on a shorter deal. I'm not sure how much they care about the increase in AAV -- they care, but perhaps considered it a worthwhile risk to see what he'd do/command? Now there's probably no getting around the 5-6 year term.

 

[chrisfont9]

In negotiations, the first offer anchors the discussion. That is, if the initial offer from the Red Sox was 4/$70M, they are certainly hoping to end up at 5/$100M or so. There has been a lot of hot air in this thread about those offers being appropriate, but that's an extremely Red Sox-centric view. Neither one are anywhere near Lester's market rate.
 
When faced with an extreme lowball offer, the appropriate negotiation tactic is to NOT make a counter offer. The correct move is to declare the initial offer as an inappropriate starting point for further discussion. That way, the negotiations are not tainted by the initial low anchor, and the counterparty is forced to come back with a more appropriate offer without knowledge of exactly what hometown discount Lester has in mind. Or, as seems to be currently happening, the stalemate increases Lester's leverage over the course of the season.

agree

 

[chrisfont9]

How many people want to sign Lester for $140 million or more? 

Me. We have enough inexpensive young guys, even inexpensive veterans, to handle an overpay on a guy who's as solid a starting pitcher as you're gonna get.

 

[nvalvo]

And if I'm Lester, I have no idea what I would sign for.  Lester is probably being told by the Levinsons that he at minimum will get Tanaka money.  Given how much money is sloshing around baseball, that's probably accurate.  How many people want to sign Lester for $140 million or more? 

 
I think I probably do. We have a lot of space in the projected payroll for the next five/six years due to players coming off the books being replaced by pre-arb and pre-FA players. 
 
I'd be more comfortable with a deal around $100-120, sure, but as I understand the state of the budget, there should be room for a SP at $25m/year for the next six years without much scrimping elsewhere. 

 

[Rasputin]

I'd probably go 140 if I had to. We're going to have a lot of young cheap players on the roster four the next several years and the difference between what we want to pay Lester and what he wants to be paid is only five or six million a year.

 

[Lose Remerswaal]

We need someone to hack the Red Sox trade computer and FAST, just to prove 90% of the assumptions (read: "wild ass guesses") as incorrect.

 

[BosRedSox5]

I wonder how Astros fans are taking this. I think we'd all be pissed if the Sox private trade talks were released... you know, after we finished analyzing the shit out of them. 

 

[dcmissle]

I'd probably go 140 if I had to. We're going to have a lot of young cheap players on the roster four the next several years and the difference between what we want to pay Lester and what he wants to be paid is only five or six million a year.

6 x 25 = 150

Less 10% hometown discount = 135

AAV at 22.5

Or something like this. Once you decide you really want the player, it's not that hard to figure out and get done.

You don't dick around with lowball offers, nor do you let something crumble over 10 MM.

Lester has made these statements. You test them and him. Make it very difficult to walk away from one hell of a lot of guaranteed money that represents fair compensation.

4 for 70 or whatever does not come remotely close to posing a difficult choice.

 

[LondonSox]

I still think the Sox are either intentionally staying away from big contracts period, or have totally misjudged the trend in market pricing for contracts.
 
I would hope that the former is flexible for the super super stars, otherwise it's ALL on the farm.
If it's the second then they need to get a grip, and adjust.
 
With what the farm is throwing out, I don't even disagree, you get a good deal (like Pedey's) fine, you get a shot at a Stanton, fine.
A guy you have two kids ready and willing to step in tomorrow for, I can see why you'd play hardball.
 
But shit we know rookies can struggle and take time to adjust, and the Sox aren't exactly a patient team. Bedding in more rookies now seems a bit crazy. I mean you have X, Mookie, JBJ, RDLR, Holt etc already.
 
Having a long term guy, who has been mainly solid with occasional excellence who would have a solid but below market deal..... You reject because???
 
Say Lackey sits out next year in a contract tantrum, and Lester goes.
Are the Sox going to next year with Buchholz, Doubrant, Workman, RDLR and Webster or Ranaudo?
 
I mean the talent is there, and the depth still has Owens, Barnes and the loser of those 6 names. Which frankly is pretty great. But could you go into next year with that rotation and expect to contend? (No)

 

[Rico Guapo]

But could you go into next year with that rotation and expect to contend? (No)

 
The flip side is that you pony up 6/150 for Lester, and he gets hurt or starts to badly underperform, and a large chunk of your payroll gets tied up in a bad contract until it rolls off the books (see Sabathia, CC). The Yankees have the financial resources/financial irresponsibility to absorb those mistakes, I'm not sure the Red Sox do, or that the FO is willing to take those same risks. 
 
If I'm the Red Sox I'd rather roll the dice on the kids, and play the probabilities game with them, than back myself into a corner with one player.

 

[glennhoffmania]

 
The flip side is that you pony up 6/150 for Lester, and he gets hurt or starts to badly underperform, and a large chunk of your payroll gets tied up in a bad contract until it rolls off the books (see Sabathia, CC). The Yankees have the financial resources/financial irresponsibility to absorb those mistakes, I'm not sure the Red Sox do, or that the FO is willing to take those same risks. 
 
If I'm the Red Sox I'd rather roll the dice on the kids, and play the probabilities game with them, than back myself into a corner with one player.

 
I don't understand this reasoning.  It's very difficult to fill a whole rotation with cost-controlled, young pitchers and still expect to compete.  With Lackey potentially up in the air and Buchholz' issues, there is not one reliable starter on the roster for 2015.  This team can handle a payroll of $175m or so.  There is absolutely no reason to go into next season with the current pitching minus Lester.
 
If they don't feel that Lester is the right guy to sign to a big contract, fine.  Then they need to allocate the resources somewhere else, like Scherzer.  Rolling the dice on a bunch of kids and Buchholz shouldn't even be an option.

 

[dcmissle]

Otherwise known as the guy who turned down 6 for 144 ... Scherzer

 

[smastroyin]

Having the proven performers is what grants you the ability to take the chances.  If Clay Buchholz were more of a sure thing and Doubront wasn't so terrible this year you could go Lackey/Buchholz/Doubront/Workman/RDLR/Webster with some minor league vet to stash in Pawtucket and the hope that Barnes and Ranaudo can step in and provide some innings.  But since I don't have a lot of faith in Buchholz or Doubront to hold their spots well, it would be nice to have Lester at the top.

 

[Tyrone Biggums]

I'd probably go 140 if I had to. We're going to have a lot of young cheap players on the roster four the next several years and the difference between what we want to pay Lester and what he wants to be paid is only five or six million a year.

I want Lester to stay too but 140 is very risky. I wouldn't mind 110, maybe 120 but 140 is a little much. If that's the case then they need to trade him before the deadline.

 

[glennhoffmania]

Otherwise known as the guy who turned down 6 for 144 ... Scherzer

 
I'm not necessarily advocating for Scherzer.  But the fact is that's what top starting pitching is going for.  We can all bitch and moan about it or accept the fact that if you want to sign someone of Scherzer's or Lester's caliber the price tag is going to approach $150m.  If not, we have to accept the fact that the rotation could be anchored by Buchholz next year or, if we're lucky, Lackey.

 

[dcmissle]

 
I'm not necessarily advocating for Scherzer.  But the fact is that's what top starting pitching is going for.  We can all bitch and moan about it or accept the fact that if you want to sign someone of Scherzer's or Lester's caliber the price tag is going to approach $150m.  If not, we have to accept the fact that the rotation could be anchored by Buchholz next year or, if we're lucky, Lackey.

Oh, I'm with you on all these points. I was just noting that Scherzer took Joe Flacco highway and will be unattainable to anyone gagging on the realistic numbers being passed around for Lester.

 

[LondonSox]

Let's also remember the farm has talent coming too. Drew's waste of money is likely to be replaced by a kid (my money might be on Marrero, the D is ready and by year end he'll be close and if he's a year away X plays SS and ?(WMB/ other) at 3B)
Betts is likely a starter somewhere next year.
Vasquez and at some point Swihart at C vs AJP
Peavy is replaced with a kid.
 
There are a lot of cost savings next year already, and not clear where they use that. But it should be on stars (which there are fewer and fewer available for cash) or if not better the guys you know inside out, and has succeed (and failed) here, than overpaying for novelty value.

 

[Drek717]

I'd probably go 140 if I had to. We're going to have a lot of young cheap players on the roster four the next several years and the difference between what we want to pay Lester and what he wants to be paid is only five or six million a year.

I think a 7 year, $140M deal is probably what Lester had in mind when talking about taking a Pedroia discount myself.
 
We're all talking about how the dollars he sees as a discount might not be the same as the FO, but a key part of Pedroia's deal was the length.  It guaranteed Pedroia will retire in a Red Sox cap.  A 4 or 5 year deal doesn't guarantee that for Lester at all.  The explicit benefits he cited from a home town discount would be retiring with the same team he came up with, and I'm sure he doesn't picture himself retiring at 36 or 37 when he's in the middle of his best season to date at 30.
 
I think that is where the FO is kind of missing the boat here on how to get Lester at a reasonable price.  I'm willing to bet that $20M a season isn't going to look like very much in 2020 ML free agent dollars.  I've always felt that Andy Pettitte was Lester's best comp as a pitcher.  There are a lot of similarities (size, handedness, approach, etc.) but beyond that they've even hit many of the same peaks and valleys throughout their career.  Pettitte's big breakout season was at 25 when he posted an ERA+ of 156.  Lester's came at 24 with an ERA+ of 144.  Pettitte had a big age 30 year with an ERA+ of 135.  Lester is having his own strong age 30 year with an ERA+ of 137 so far.  Overall Lester has been better and healthier than Pettitte up to this point.
 
Pettitte pitched nearly 200 IP a season through his age 37 season.  He only had one year with an ERA+ below 100 (at 36 with a 97) every other season was more in line with his ~111 career norm except for his age 33 season when he put up an ERA+ of 177 and had an absolutely huge year.
 
Lester looks like a guy who is back to his '08-'11 form.  He's been the picture of health for years now.  His arsenal doesn't rely on velocity or raw stuff at this point, instead his results are garnered from an excellent tool set across the board and a diverse arsenal of mature pitches.  He is in basically every single way the guy you'd bet on of any pitcher to be effective into his late 30's.  If we're given the choice between not re-signing Lester, giving Lester 5-6 years at $23-$25M per, or giving him 7 years at $20M per I'd much rather take the last option (followed by the second mind you).  Make him a fixture of this organization alongside Pedroia, and just like Pedroia expect that while he'll be diminished in his late 30's the young talent coming up through the farm will be at their career peaks ready to make up the value difference in exchange for their veteran leadership.

 

[threecy]

A couple of things that I don't think have been mentioned in this thread (I don't want to reread 13 pages!)...
 
- I suspect Lester may value guaranteed years, especially considering how he almost lost it all to cancer years ago.
- I imagine he looks at the Lackey contract to an extent, considering he's a teammate and was a similar age when he signed it with the Sox (5 years/82.5M) about half a decade ago.  Based upon the CPI, that contract in 2013 dollars would be 5 years/$90 million.

 

[IdiotKicker]

The more I look at this situation, the less I really understand what the FO is doing here.  The entire point of having a strong farm system isn't so you can build a team of cheap players just for the sake of doing so.  It's so that you can then use the resources freed up by having players on below-market contracts for those that produce consistent value to be resigned, traded for, or signed as free agents.  Lester, excluding 2012, which is completely out of line with just about every other stat he has put up, is the epitome of consistent value. He falls perfectly into a 1A/2 role in a rotation, eats innings every year, and is the exact type of player that you sign to a long-term deal.
 
One thing I've been doing recently is looking at baseball teams in terms of risk management.  There are really three types of risk that you have with a team.  You have injury/decline risk for players signed long-term.  You have replacement risk for players who are up at the end of the year.  And you have development risk for rookies expected to take over major roles.  Being too reliant on any of those areas tends to get a team into trouble.  If you resign everyone, you end with a shitload of big contracts and the inability to get better-producing assets in.  If you resign no one, you potentially end up taking on decline risk, or you are stuck with mid-level replacements.  If you rely entirely on developing players, you have to deal with flameouts and potentially end up with replacement risk anyways.  And so just like anything else, you want to diversify the risks you take, so that you have a balance that allows as much flexibility as possible.  That way if players in any category are underperforming, you have the ability to go out and modify your club as you see fit.
 
With all of the potential cheap assets that you have coming to the majors over the next several years, if there was ever one place to spend money, this would be it.  Especially since if you're looking at a 5-6 year deal, you're talking about it expiring as a lot of those entry-level deals are coming out of arbitration, so it frees up the cash at the right time anyways.  I get that 6/$135 is a lot of cash to shell out.  But the very nature of how this club is set up enables them to take this risk here, since they have so much development risk coming up.

 

[HriniakPosterChild]

I wonder how Astros fans are taking this. I think we'd all be pissed if the Sox private trade talks were released... you know, after we finished analyzing the shit out of them. 

I would guess all five of them are pretty ticked off.

 

[nattysez]

Old Hickory is not happy.
 

Red Sox Last in R, 14th in OPS,12 in HR. When they signed Pedroia, he gave back $ on org. competitiveness. Now see Lester shortsheeted
 

https://twitter.com/pgammo/status/484002133164183552

 
If Sox sign Lester, it'll be double their offer. If they try to replace him, even more $, and draft choice.
 

https://twitter.com/pgammo/status/484002563113885696

 

[dcmissle]

The more I look at this situation, the less I really understand what the FO is doing here.  The entire point of having a strong farm system isn't so you can build a team of cheap players just for the sake of doing so.  It's so that you can then use the resources freed up by having players on below-market contracts for those that produce consistent value to be resigned, traded for, or signed as free agents.  Lester, excluding 2012, which is completely out of line with just about every other stat he has put up, is the epitome of consistent value. He falls perfectly into a 1A/2 role in a rotation, eats innings every year, and is the exact type of player that you sign to a long-term deal.
 
One thing I've been doing recently is looking at baseball teams in terms of risk management.  There are really three types of risk that you have with a team.  You have injury/decline risk for players signed long-term.  You have replacement risk for players who are up at the end of the year.  And you have development risk for rookies expected to take over major roles.  Being too reliant on any of those areas tends to get a team into trouble.  If you resign everyone, you end with a shitload of big contracts and the inability to get better-producing assets in.  If you resign no one, you potentially end up taking on decline risk, or you are stuck with mid-level replacements.  If you rely entirely on developing players, you have to deal with flameouts and potentially end up with replacement risk anyways.  And so just like anything else, you want to diversify the risks you take, so that you have a balance that allows as much flexibility as possible.  That way if players in any category are underperforming, you have the ability to go out and modify your club as you see fit.
 
With all of the potential cheap assets that you have coming to the majors over the next several years, if there was ever one place to spend money, this would be it.  Especially since if you're looking at a 5-6 year deal, you're talking about it expiring as a lot of those entry-level deals are coming out of arbitration, so it frees up the cash at the right time anyways.  I get that 6/$135 is a lot of cash to shell out.  But the very nature of how this club is set up enables them to take this risk here, since they have so much development risk coming up.

Success is getting the big things right, and sometimes even very smart people have difficulty with it. Perhaps this is purely reactionary. Ben pulled the miracle of this century to date getting them out of some onerous and limiting contracts, they have since won a WS, and they don't want to be back in that position anytime soon.

The problems with viewing things that way are multiple and pretty obvious -- from the outside.

From a competitive and commercial perspective, the risk adverse path here is pretty clear. I hope the fog of war doesn't obscure it.

 

[Rasputin]

I want Lester to stay too but 140 is very risky. I wouldn't mind 110, maybe 120 but 140 is a little much. If that's the case then they need to trade him before the deadline.

 
This I don't get. The difference in risk between 140 and 110 spread out over six years is pretty trivial, all things considered. It's five million per year and sure, that's not chump change, you can get a useful player for that, but it's pretty unlikely that the five million is going to be the difference between a contract of that size being good or bad. 
 
I mean, if the Sox sign him for 6/110 and he pitches brilliantly right up to the 2015 ASG where he tries to lift Prince Fielder, tearing his arm to shreds and requiring a Tommy John surgery precisely placed to fuck up two seasons, then suffers age related decline into horribleness the last couple years of the contract, it's going to be a disaster whether it's 110 or 140.

 

[BosRedSox5]

Ben pulled the miracle of this century to date getting them out of some onerous and limiting contracts, they have since won a WS, and they don't want to be back in that position anytime soon.

 
It was definitely one of the best trades in Red Sox history, but let's not forget that Adrian Gonzalez wasn't really one of the onerous contracts they gave up. He was the prize we had to surrender to get rid of the onerous contracts. 

A-Gone is exactly the kind of player teams should be interested in giving mega deals to. He's a high character guy, very durable, is multidimensional and is a good face of the organization. Sure, he's struggled a bit in Los Angeles, but at the time he was an absolute stud, hit well in San Diego and was really just made for Fenway. It was Beckett who had a big contract, a bad attitude and the team wasn't planning on re-signing him after his contract was up. Crawford's contract was the one that really sucked. 

Lester is the type of pitcher the Sox should make a big commitment to. He's high character, and durable and a good face of the franchise. He's the type of dude who's worth a big contract. If Crawford and Beckett weren't part of the equation we'd still have A-Gone playing 1B for 21 million a season and we'd be happy about it. 

Certainly they don't want to get in contract trouble again. They were definitely handcuffed by Beckett and Crawford and Gonzalez on top of that, but offering one mega deal to a guy like Lester with no other big financial commitments on the horizon is a move that would make sense. 

 

[snowmanny]

I guess the question is whether the Red Sox have an actual intention of signing him. His price has presumably gone up since ST and will continue to go up barring injury, so it's curious why he isn't signed. If this ends with one of those disingenuous/face-saving November offers (one that probably would have been accepted in March but is well below the free agent market and sure to be rejected a la Clemens) I'll be disappointed.

 

[glennhoffmania]

The fact that he isn't signed yet makes me think there are two possible things going on:
 
1. As Snowmanny said, they may not ever intend to sign him.  Maybe they set an absolute ceiling at something like 5/100 and Lester said not even close.  So now they're just going through the motions and the chances of him resigning are basically zero.
 
2. They wanted to see how he got through this season, both in terms of health and performance, and then they'll give him whatever it takes.  So maybe they could've had him at 6/130 in March, but they didn't want to be exposed for all of 2014 before the contract even kicked in.  So now if it costs 6/150 they view that extra 20m as kind of a 2014 insurance policy and they're fine with that deal.

 

[Stitch01]

2) seemed likely and reasonable to me to start the season.  I hope they don't come back now expecting the same kind of hometown discount.
 
Its possible that they have a  good plan that doesn't involve reupping Lester, but the '15 team needs Lester or another high-end veteran starter

 

[Rovin Romine]

 
It was definitely one of the best trades in Red Sox history, but let's not forget that Adrian Gonzalez wasn't really one of the onerous contracts they gave up. He was the prize we had to surrender to get rid of the onerous contracts. 

A-Gone is exactly the kind of player teams should be interested in giving mega deals to. He's a high character guy, very durable, is multidimensional and is a good face of the organization. Sure, he's struggled a bit in Los Angeles, but at the time he was an absolute stud, hit well in San Diego and was really just made for Fenway. It was Beckett who had a big contract, a bad attitude and the team wasn't planning on re-signing him after his contract was up. Crawford's contract was the one that really sucked. 

Lester is the type of pitcher the Sox should make a big commitment to. He's high character, and durable and a good face of the franchise. He's the type of dude who's worth a big contract. If Crawford and Beckett weren't part of the equation we'd still have A-Gone playing 1B for 21 million a season and we'd be happy about it. 

Certainly they don't want to get in contract trouble again. They were definitely handcuffed by Beckett and Crawford and Gonzalez on top of that, but offering one mega deal to a guy like Lester with no other big financial commitments on the horizon is a move that would make sense. 

 
Just sort of riffing off this - I think the lesson the Sox have most recently learned is that they had to bail on a 2012 season because they didn't have financial flexibility AND they were locked into too many big contracts.  
 
Crawford had poor 2011 (age 29) and 2012 before going down.  21 mil per year to 2017.
Gonzo had a good 2011 (29) and then morphed into a .800 OPS hitter (which he remains, so lets not say the Gonzalez deal was a good one.)  21 mil per year to 2017
Beckett had a good 2011 (31) and then fell off a cliff in 2012.  17 mil per year to 2014.
Lackey was injured in 2011 (32) and didn't play at all in 2012.  16 mil per year to 2014. 
Youkilis was trending downward in 2011 (32) (although he remained very serviceable) and lost his job in 2012.  12 mil to 2012
Dice-K was awful/injured in 2011 (30) and 2012.  10 mil each year. 
JD Drew was poor in 2011 (35). 14 mil. 
We can add Bobby Jenks and Mike Cameron in with the guys who went down for the count and sucked up a decent amount of money.
 
All of those contracts looked decent when signed, and those that didn't (Lackey, Crawford, and to some extent Beckett) were popularly hailed along the lines of "they made a slight overpay, but it's OK - it's what we need to be competitive."  I mean, where else would we find an ace besides Beckett?  He was entering his prime.  
 
The Punto Trade is sometimes underestimated I think.  It not only cleared deadwood (Gonzalez goes in that category), but it brought back some young arms, and gave us enough flexibility to sign "mid-tier" FAs to balance our lineup.  Prior to the trade, there wasn't financial room to trade for FAs mid-season.  Also, it tied our fortunes to a bunch of "maybe they'll come back, maybe they will recover, maybe they'll defy time" players.  
 
***
Anyway, I don't think the Sox want to sink a lot of money into older players.  Some of it may be a once bitten twice shy thing.  Some of it might simply be looking forward.  
 
According to Cots, next year we have 70 million tied up in: Napoli, Ortiz, Pedroia, Victorino, Buchholz, and Mujica.  Based on this year's performance so far, they're not really a squad that's a lock to provide above average value for the collective money.  (They *might* do so, but my point is that it's kind of a crapshoot right now, due to Napoli's hips, Ortiz's age, Pedroia's lack of power, Victorino's injuries, Buchholz's inconstancy, and Mujica's Mujica.)
 
While it would be the first year of Lester's contract, where his value is potentially the highest, I'm sure the FO is balancing rookie development against potential FA opportunities.  I think they're prepared to spend on the FA market, but even one big signing flop can drag down the team, while two or three can cripple - and the more eggs you have in the "over-30" basket. . . 

 

[Bone Chips]

I hate to bring this up, but is it possible the Sox may have some additional trepidation due to the non-Hodgkin lymphoma? I mean, it's not the type of thing you're ever really free from. Are the chances of recurrence great enough to justify a more conservative approach than they normally would have? The reason I ask is that things don't seem to be adding up otherwise.

 

[wade boggs chicken dinner]

 
****
Anyway, I don't think the Sox want to sink a lot of money into older players.  Some of it may be a once bitten twice shy thing.  Some of it might simply be looking forward.  
 
According to Cots, next year we have 70 million tied up in: Napoli, Ortiz, Pedroia, Victorino, Buchholz, and Mujica.  Based on this year's performance so far, they're not really a squad that's a lock to provide above average value for the collective money.  (They *might* do so, but my point is that it's kind of a crapshoot right now, due to Napoli's hips, Ortiz's age, Pedroia's lack of power, Victorino's injuries, Buchholz's inconstancy, and Mujica's Mujica.)
 
While it would be the first year of Lester's contract, where his value is potentially the highest, I'm sure the FO is balancing rookie development against potential FA opportunities.  I think they're prepared to spend on the FA market, but even one big signing flop can drag down the team, while two or three can cripple - and the more eggs you have in the "over-30" basket. . . 

 
The front office has made it known that they view long-term deals for players in their 30s with skepticism.  Since it's not my money, I'm with the posters who are skeptical of building championship teams without ever getting into such deals.
 
OTOH, there is so much money sloshing around the system that paying market value to FAs (or "slightly under market value" for soon-to-be-FAs) is not an efficient use of resources.
 
Lester seems like a great guy and personally, I certainly would be thrilled if the Sox kept him for the rest of his career, whether it be for $70M, $100M, or $150M.  Like I said it's not my money.  But I get the feeling that if current management is going to give out a six- or seven-year deal to a pitcher in his 30s, it's not going to be to Lester.
 
So hopefully I am wrong.

 

[seantoo]

As a fan, yes, I see that winning is highly important, and the long-term health of the team is vital for sustained winning. No problem.
 
But I also want to see the best players play. You look around the league, and Kershaw is throwing 28 straight scoreless and Cueto gives up a run every other start and King Felix is putting up double-digit strikeouts on the regular. I want one of those guys. Lester is one of those guys.
 
The Dodgers backed up the truck for Kershaw, and while Lester is not at the same career point, I want the Sox to do the same. Give him all the money. He's a big strong lefty with a love of the big stage and low injury risk. I don't care if the last couple years of the deal are an overpay. The Sox need him as an anchor, and, as a fan, I need to see some kind of commitment to putting elite talent on the field.
 
Ok, Ellsbury isn't going to be elite talent going forward. I can get that argument. But it doesn't fly with Lester. Give him the money.  

Define that, and there in lies the issue.

 

[seantoo]

 
It was definitely one of the best trades in Red Sox history, but let's not forget that Adrian Gonzalez wasn't really one of the onerous contracts they gave up. He was the prize we had to surrender to get rid of the onerous contracts. 

A-Gone is exactly the kind of player teams should be interested in giving mega deals to. He's a high character guy, very durable, is multidimensional and is a good face of the organization. Sure, he's struggled a bit in Los Angeles, but at the time he was an absolute stud, hit well in San Diego and was really just made for Fenway. It was Beckett who had a big contract, a bad attitude and the team wasn't planning on re-signing him after his contract was up. Crawford's contract was the one that really sucked. 

Lester is the type of pitcher the Sox should make a big commitment to. He's high character, and durable and a good face of the franchise. He's the type of dude who's worth a big contract. If Crawford and Beckett weren't part of the equation we'd still have A-Gone playing 1B for 21 million a season and we'd be happy about it. 

Certainly they don't want to get in contract trouble again. They were definitely handcuffed by Beckett and Crawford and Gonzalez on top of that, but offering one mega deal to a guy like Lester with no other big financial commitments on the horizon is a move that would make sense. 

This is an excellant point that far to many seem to miss here. The Sox are not opposed to big contracts in fact to get elite talent that is what it takes. The age and history of the player has to be right for a long term commitment to make sense and that scenario rarely happens.

 

[Plympton91]

This is an excellant point that far to many seem to miss here. The Sox are not opposed to big contracts in fact to get elite talent that is what it takes. The age and history of the player has to be right for a long term commitment to make sense and that scenario rarely happens.

So when that situation doesn't exist, we should all just be happy that John Henry is booking $100 million in extra profit, while we watch a glorified AAA team struggle to achieve respectability?

Look at RRs list of what they've got locked up for 2015 at $70 million. Pretend that Lackey's coming back at a discount because of his option so it's $80 million including Lackey. You're ok if the rest of that team is Vazquez, Middlebrooks, Bogaerts, Bradley, Betts, Workman, DLR, Ranaudo etc for a total payroll of $100 million? When did this team become middle market again?

 

[LondonSox]

In fairness, just because you CAN spend it doesn't mean you SHOULD.
Keeping your powder dry rather than buy the shiniest thing that is available RIGHTTHISSECONDNOWIWANTITNOW!!11! can be a very good decision. IF there is a plan.
 
But I'd love to know the plan. Because there needs to be a good one, the next year or two defines the next decade imo

 

[glennhoffmania]

So when that situation doesn't exist, we should all just be happy that John Henry is booking $100 million in extra profit, while we watch a glorified AAA team struggle to achieve respectability?

Look at RRs list of what they've got locked up for 2015 at $70 million. Pretend that Lackey's coming back at a discount because of his option so it's $80 million including Lackey. You're ok if the rest of that team is Vazquez, Middlebrooks, Bogaerts, Bradley, Betts, Workman, DLR, Ranaudo etc for a total payroll of $100 million? When did this team become middle market again?

 
Come on.  What do you think the realistic odds are that they go into 2015 with a payroll of around $100m?  There's no way that happens.  Just because they didn't make a couple of moves that you wanted them to make, and they didn't hold a press conference to give a detailed explanation for why they didn't make those moves, doesn't mean there weren't totally valid reasons for the decisions.  To me, what the current 2015 payroll suggests is that they're going to spend a lot of money this offseason, either by signing FAs (Lester, Scherzer or Shields, for example) or trading some prospects for an elite player or players.  What is the basis for thinking that they're going to cut ~$60m in payroll?  Has Ben or JWH ever even hinted at that?

 

[dcmissle]

In fairness, just because you CAN spend it doesn't mean you SHOULD.
Keeping your powder dry rather than buy the shiniest thing that is available RIGHTTHISSECONDNOWIWANTITNOW!!11! can be a very good decision. IF there is a plan.
 
But I'd love to know the plan. Because there needs to be a good one, the next year or two defines the next decade imo

Last sentence capitalized, bolded and underscored. And for commercial as well as on-the-field competitive reasons. Last year's trophy bought FO a couple of years of fan patience, at least with me. But it never will buy them 5 in this town, and if they find themselves in 2016 with promising young roster that is a top of rotation guy short of being genuinely competitive, there will be hell to pay, and there should be. This is not a shoestring operation, and investing in your own player, who BTW is already historically important to this franchise, strikes me as the ultimate no brainier and safe play, unless Lester becomes very unreasonable.

(And yes, thank your lucky stars for the AGon signing, the get-out-of- jail card for inexplicably bad contract given to Crawford.)

 

[Smiling Joe Hesketh]

 
Come on.  What do you think the realistic odds are that they go into 2015 with a payroll of around $100m?  There's no way that happens.  Just because they didn't make a couple of moves that you wanted them to make, and they didn't hold a press conference to give a detailed explanation for why they didn't make those moves, doesn't mean there weren't totally valid reasons for the decisions.  To me, what the current 2015 payroll suggests is that they're going to spend a lot of money this offseason, either by signing FAs (Lester, Scherzer or Shields, for example) or trading some prospects for an elite player or players.  What is the basis for thinking that they're going to cut ~$60m in payroll?  Has Ben or JWH ever even hinted at that?

 
Right.
 
According to B-Ref, the Sox are at 164.6 million payroll for 2014. Next year's obligations are currently estimated to be around 78 million, plus 20 million in option costs and another 12 in arbitration costs. Since JWH and friends bought the team, there's never been a year where they slashed payroll drastically and took profits like mad.
 
2003: 100M
2004: 125M
2005: 121M
2006: 120M
2007: 143M
2008: 133M
2009: 122M
2010: 162M
2011: 161M
2012: 173M
2013: 150M
2014: 164M
 
There's less than 0% chance that the Sox start the 2015 with a payroll around 100M while "John Henry is booking $100 million in extra profit, while we watch a glorified AAA team struggle to achieve respectability." That's total bullshit. Even when the 2012 season went pear-shaped, it wasn't because they didn't spend money, it was because every choice they made on where to spend that money, especially on the manager, was straight out of the Nick Cafardo school of Dunderheaded Baseball Decisions.
 
The team is struggling on the field in 2014, but not for lack of payroll. Their ownership history has shown they will spend on players. We can argue the strategy they use (ie is it better to pay a ton  of money for one "premium" player or mitigate risk by spending the same money on several "mid-sized" players), but not IMO the willingness to spend on the on-field product.

 

[Rovin Romine]

So when that situation doesn't exist, we should all just be happy that John Henry is booking $100 million in extra profit, while we watch a glorified AAA team struggle to achieve respectability?

Look at RRs list of what they've got locked up for 2015 at $70 million. Pretend that Lackey's coming back at a discount because of his option so it's $80 million including Lackey. You're ok if the rest of that team is Vazquez, Middlebrooks, Bogaerts, Bradley, Betts, Workman, DLR, Ranaudo etc for a total payroll of $100 million? When did this team become middle market again?

 
I'll ignore the trolling, but this is a good post to spring off of.  
 
Let's look at it another way, from the bottom up; there's a minimum amount of $ the Sox need to field "the rest of the team," apart from "premium or elite or star" FA players.  
 
Right now the "rest of the team" cost looks low for the next couple of years due to rookies and pre-arb players.  Of course, we also suck ass.  So we may need to replace some of those players.   In 2014 and beyond, I'd expect money to be spent for all levels of free agent, including what I'd call "reliable, mid-tier" FAs.  The 2012 class of FAs, including Victorino and Napoli fall into that category for me.  Those were guys who weren't sexy, but seemed successful enough to fit on the Sox - they were slightly overpaid to land them.  Some of the future FA signings will work out, and some won't, so we'll need some redundancy/depth in the system. It would also be wise to have a gap or margin of unspent money which we can use to subsidize a bad contract in a trade and/or take on salary in a midseason trade, a la Peavy.
 
The above gives the Sox a target number for the money they need to budget to field a competitive team.  Whatever is left over, up to the cap, they can spend on Premium FAs or players with market setting contracts.  It's not an infinite number.  They're already paying out significant money to players who may or may not prove worth it next year.   It does not make any sense to keep adding marginal/risky Premium FA players year after year.  Sooner or later, you're going to get locked into those untraceable contracts.  Just like the Sox were in 2012 before the Dodgers Ex Machina.  
 
I don't know how Lester fits in.  He's getting older, and as pointed out in the other thread, seems somewhat reliant on Ross in terms of stealing strikes this year.  On the other hand, he's been pretty consistent - let's call him a #1-2 SP for short.  If he can keep that up, Lester has real value.  However, if the Sox expect Lester to devolve into a #2 then a #3 SP, it makes little sense for them to pay premium money for him.  (It's also unlikely that Lester will become a true #1, though he's shown himself capable of truly excellent runs.) 
 
My point is that the budget isn't infinite and teams compete within the framework of the luxury tax "cap."   Tossing future money out the window because they're in a hurry to spend up to their annual budget will only hurt them in the long run.   Yesterday it was Ortiz.  Today it's Lester and Uehara.  Tomorrow it will be Buchholz.  
 
**
Or look at it this way.  We're currently spending 156 Mil.  If we resigned everyone, we could field the same shitty team and use 20 mil to give everyone raises: 7 to Lester, 7 for a QO to Uehara, 7 in arb.  No upgrades on the FA market.  
 
**
 
Also, let's not forget Dempster left 13 mil on the table this year.  If he insisted on pitching, we'd be at 170 to open the year.  According to Cots, that would be our second highest payroll after 2012 (175 mil).  

 

[Yelling At Clouds]

Not to be that guy, but there is a "2015 payroll" thread...

 

[Bone Chips]

Their ownership history has shown they will spend on players. We can argue the strategy they use (ie is it better to pay a ton  of money for one "premium" player or mitigate risk by spending the same money on several "mid-sized" players), but not IMO the willingness to spend on the on-field product.

 
Yeah, but the ownership group also got burnt on player spending and has given strong indications the last year that they have changed their strategy pretty drastically moving forward.  And by that I mean - no longer a player in the top-tier free agent market.  When your stated strategy is that you don't want to give out long-term contracts to players over 30, well that pretty much says you are no longer going to compete for top-tier players anymore.  Free agents are basically all over 30, and the ones with any high value are going to demand deals of 4 years or longer.  They are not even showing a willingness to do what is necessary to retain free agents that have grown up through their system (Ellsbury and Lester).  So we can look to their past track record all we want, but it's what they are doing now and in the future that has me concerned.
 
I don't think the Red Sox are going to morph into a $100 million payroll team, and I'm sure P91 doesn't either.  But I am having a hard time reconciling all the pieces in their overall strategy in such a way that you can have a $170 million payroll with this team going forward.  How many $10 million a year free agents can you add to their roster?  They are loaded with low cost young players that making the bare minimum.  It seems like the perfect strategy for such a team in this poisition is to target a couple top-tier free agents at this time - not avoid them.

 

[Smiling Joe Hesketh]

 
Yeah, but the ownership group also got burnt on player spending and has given strong indications the last year that they have changed their strategy pretty drastically moving forward.  And by that I mean - no longer a player in the top-tier free agent market.  When your stated strategy is that you don't want to give out long-term contracts to players over 30, well that pretty much says you are no longer going to compete for top-tier players anymore.  Free agents are basically all over 30, and the ones with any high value are going to demand deals of 4 years or longer.  They are not even showing a willingness to do what is necessary to retain free agents that have grown up through their system (Ellsbury and Lester).  So we can look to their past track record all we want, but it's what they are doing now and in the future that has me concerned.
 
I don't think the Red Sox are going to morph into a $100 million payroll team, and I'm sure P91 doesn't either.  But I am having a hard time reconciling all the pieces in their overall strategy in such a way that you can have a $170 million payroll with this team going forward.  How many $10 million a year free agents can you add to their roster?  They are loaded with low cost young players that making the bare minimum.  It seems like the perfect strategy for such a team in this position is to target a couple top-tier free agents at this time - not avoid them.

 
They gave Dustin Pedroia 8/110 just last year one month before he turned 30. I mean, yeah, technically that doesn't violate the bolded as he wasn't an FA yet, but there's very little difference there.
 
Are they going to spend a lot of money on the payroll? Most assuredly. The rest is just semantics, whether to spend it on a few players making huge money or more players making lesser money. There's risk no matter what they do. There was risk in signing Victorino to 3/39 given his injury history, and here we are today seeing that in action after seeing the high points of that contract last year. The Sox gave Mike Lowell 3 years after 2007 and that turned out to be 1 year too many as Lowell calcified quickly. There are no sure things, of course, so the Sox are looking to mitigate their risk.

 

[Rovin Romine]

But wait....I know the first year worked out, but wasn't there risk in a guy like Victorino? Wasn't there risk in Dempster? They were shorter duration deals than the upper echelon FA's, but they also didn't have nearly as much upside. If you are only willing to give out deals of up to 3 years (at a maximum of $13M, say), than you are going to completely close yourself out of a certain market segment. That's OK when you have high level performers in their prime. I'm just not sure the Sox really have much of that going forward (Bogaerts being a likely exception).

Granted, that was a strategy and I'm sure the Sox will adjust. In order to retain Lester and / or add a comparable pitcher (and at least a bat or two), they are probably going to have to give out deals they aren't all that comfortable with.

 
I agree.  There's always risk, but the stuff being risked is different, e.g., a 3 year deal for 36 v. a 6 year deal for 120.  A team with multiple large, long term contracts can have their competitive edge eaten away if a couple of those guys are injured or drastically underperform.  This is because they're guaranteed contracts and you don't get the money/resources back.  Plus you usually play the underperforming guy, blocking other players. 
 
I think people have already become blasé about the Punto trade.  Having Crawford, Gonzalez, and Beckett still on board would have crippled the franchise in 2012, 2013, 2014.  Those three players were owed 57 mil for those 3 years.  While there's been some bounce back, none of them turned out to be a franchise level player for LA. 

 

[Bone Chips]

 
I think people have already become blasé about the Punto trade.  Having Crawford, Gonzalez, and Beckett still on board would have crippled the franchise in 2012, 2013, 2014. 

How have the Dodgers done since the trade?

 

[snowmanny]

I am confident the Red Sox will spend to and occasionally beyond the luxury tax threshold as they have done in the past. That being said, given the support of the Boston fans and the revenue generated by us they absolutely SHOULD spend the money available to them. Most fans would be justifiably upset if they trotted out a $115Million fourth-place team, and I do not believe they ever would.

I would bet the Drew signing was actually an example of them paying him more than they thought he was actually worth because they had the money available.