Lester: Stop Believing What You Read on Twitter.

[ivanvamp]

At this point, seriously, they should just sign Lester for….whatever it takes.  Because benhogan is right.  The price for every pitcher in his class would go up similarly.  So if they want a true #1, they're going to have to pay big-time for it, either in a similar amount of cash, or a ridiculous haul of prospects.  So either:  (1) pay Lester, or (2) go my other proposed route and load up on #2/#3 types (Latos, Shields, Shark, Porcello, etc.) and trust that they'll be enough come playoff time.
 
Either way.  But don't not sign Lester only to either (a) pay more for Scherzer, or (b) make a ridiculous trade for a Hamels that makes you take on a similar salary PLUS lose a ton of young talent.
 
So 6/150 for Lester.  Bite the bullet.  And then deal Cespedes+ for a #2.

 

[HurstSoGood]

Good grief. What do we want from this guy?
Jon Lester has been very, very good for and to the Red Sox. He has proven himself in Boston. He has proven himself over and over again in the grinder known as the AL East. He had one off-year/outlier in 2008 . His numbers/stats have trended in the right direction and he consistently gave us 200+ innings of quality pitching each year. His walks and WHIP have trended downward and his K rate has stayed high. Someone with a better handle on sabermetrics can fill in the blanks.
 
The price of poker here may be totally out of control, but Kershaw set the market whether we like it or not. How much would we be bidding for Bumgarner if he was a FA right now? $28M per year? $30M? More? I'd rather not give up stud prospects for 36 year-old Cliff Lee. Sherzer is going to get at least $25M per, and probably for a lot of "per's." Give Jon his 7/$154M and enjoy watching the man earn his money.
 
Time to come home, Jon.
 
Side Note: Nice numbers for Jon to aspire to.
Tom Glavine, ages 31-42 seasons(1997-'08)…many of which came during the "Steroid Era:" 
W/L 166-111, 6 time All Star, 1 CY, 1 CY Runner-Up.

 

[geoflin]

 
- Include some really big incentives for stuff like Cy Young Awards and Playoff MVPs. Might be a good pot-sweetener to throw in a $2M incentive for a CYA. Expensive, yes, but even if it took his annual salary to say $27M, it would mean he's arguably out-pitching the likes of Hernandez, Sale, etc...

 
I've always had an issue with this type of contract. Seems to me that anyone who is being paid north of $20 million per year should be expected to make the All Star team and either be in contention for or win individual awards. If they're not good enough to do that, why pay them that kind of money? I'd rather see them give back money (not that it would ever actually happen or anyone would sign that type of contract) for any year they don't make the All Star team or be in contention for individual awards. 

 

[lxt]

Is it just me or are we talking crazy money. It seemed that a month ago we said 6/$110. Then two weeks ago it was 6/$120. Last week it was 6/$130. Now we're talking 6/$140-150. Timeframes may be off a tad.
 
I draw a line and offer 6/$144 - take it or leave it. As much as I'd like him back there is a point where you got to say enough is enough. I'd suggest alternatives but that's not for this "thread/Board".

 

[Rough Carrigan]

Cross the Braves off the list.
 
David O'Brien @DOBrienAJC
#Braves did not make an offer to Lester. Saw where price was going and didn't think they could make competitive offer.

Liberty Media has a fuckton more money than John Henry, Tom Werner and Grinch Lucchino put together.  They make bullshit low, fake payments for the rights to Braves games and run that team with a budget closer to that of the Rays than that of the Red Sox.  There was no way they were going to spend 20-25% of their payroll on one starting pitcher if they kept running the team the way they have been.

 

[BornToRun]

 
Fuck that. Be happy if Scherzer goes to the Cubs. Be pissed off if Lester goes anywhere but here.

Seconded. Fuck the Cubs. They can have Scherzer.

 

[Yelling At Clouds]

At this point, seriously, they should just sign Lester for….whatever it takes.  Because benhogan is right.  The price for every pitcher in his class would go up similarly.  So if they want a true #1, they're going to have to pay big-time for it, either in a similar amount of cash, or a ridiculous haul of prospects.  So either:  (1) pay Lester, or (2) go my other proposed route and load up on #2/#3 types (Latos, Shields, Shark, Porcello, etc.) and trust that they'll be enough come playoff time.
 
Either way.  But don't not sign Lester only to either (a) pay more for Scherzer, or (b) make a ridiculous trade for a Hamels that makes you take on a similar salary PLUS lose a ton of young talent.
 
So 6/150 for Lester.  Bite the bullet.  And then deal Cespedes+ for a #2.

 
I guess I'm wondering the point at which the Hamels deal actually does become a significant bargain. Right now, he's 5/114, and to me that's a big difference from 6/150.

 

[Otis Foster]

Seconded. Fuck the Cubs. They can have Scherzer.

Plus 3. Theo used up all his good will with me when he scampered away from the 2011 pigsty.

 

[Snoop Soxy Dogg]

At this point, seriously, they should just sign Lester for….whatever it takes.  Because benhogan is right.  The price for every pitcher in his class would go up similarly.  So if they want a true #1, they're going to have to pay big-time for it, either in a similar amount of cash, or a ridiculous haul of prospects.  So either:  (1) pay Lester, or (2) go my other proposed route and load up on #2/#3 types (Latos, Shields, Shark, Porcello, etc.) and trust that they'll be enough come playoff time.
 
Either way.  But don't not sign Lester only to either (a) pay more for Scherzer, or (b) make a ridiculous trade for a Hamels that makes you take on a similar salary PLUS lose a ton of young talent.
 
So 6/150 for Lester.  Bite the bullet.  And then deal Cespedes+ for a #2.

 
Yeah, I'm on the other side of this. I hope they hold their ground and don't do that. That's a bad contract (at least for any team unfortunate enough to have a budget), and in time, it will be proven to be a terrible contract. Not signing Lester isn't the end of the world. You can go the Baltimore way and build a solid rotation of #2/#3, while maintaining payroll flexibility to build a deeper team. This is the biggest test to the discipline they've been talking about since the Punto trade (Sosh isn't really passing that Test, lol, with all the "Just give him the money!!!" wailing I've seen around here lately).
 
I admit it's quite tough. But if this goes too high (and for me, that's $130-$140m), they have to let him go.  

 

[ivanvamp]

I hear you, and I wouldn't crucify the Sox' FO if they did just that.

SO LONG AS they didn't then go out and spend more on Scherzer or make a stupid deal for Hamels, etc. if they went the alternative route you and I suggest then I'd be fine with that.

 

[Spelunker]

Henry doesn't own Manchester United. FSG owns Liverpool.

I understand your point, but there's a huge difference between the two clubs.

Very true. But, along those lines, John Henry doesn't own the Sox: FSG does. Which makes his response to comments about Henry's personal net worth still stand, no?

 

[DJnVa]

Is it just me or are we talking crazy money. It seemed that a month ago we said 6/$110. Then two weeks ago it was 6/$120. Last week it was 6/$130. Now we're talking 6/$140-150. Timeframes may be off a tad.
 
I draw a line and offer 6/$144 - take it or leave it. As much as I'd like him back there is a point where you got to say enough is enough. I'd suggest alternatives but that's not for this "thread/Board".

 
 
It wasn't $110/6 a month ago.  In the original Lester thread, the second post, on August 3rd, MakMan said $130 million, and that's where we are.
 
 
And can the "I'd suggest alternatives..." claptrap, it has no place on the main board.

 

[Sampo Gida]

Putting 25 million AAV into the context of past SP'er FA contracts in 2015 dollars (adjusted for 5% annual payroll inflation/mlb revenue growth), Only contracts over 100 million considered (except Lackey who is under and Tanaka who is over but no previous MLB experience)
 
 
Kevin Brown 105/7 in 1999, 33 mil AAV in 2015 dollars, age 34, previous 3 yr rWAR 23.5,  3 yr avg rWAR  7.8  2015 AAV/WAR 4.2 mil
Johann Santana 137/6 in 2008, 33 mil AAV in 2015 dollar, age 29, previous 3 yr rWAR 19.83 yr,  avg rWAR 6.6, 2015 AAV/WAR 5.0 mil
CC Sabathia 161/7 in 2009, 31 million AAV in 2015 dollars. age 28, previous 3 yr rWAR 17.7,  3 yr avg rWAR 5.9, 2015 AAV/WAR 5.3
Cliff Lee 120/5 in 2012, 28 mil AAV in 2015 dollars, age 32, previous 3 yr rWAR 17.1,  3 yr avg rWAR 5.7, 2015 AAV/WAR 4.9
Zach Greinke 147/6 in 2013, 27 mil AAV in 2015 dollars age 29,  previous 3 yr rWAR 8.5,  3 yr avg rWAR 2.8, 2015 AAV/WAR 9.6
Barry Zito 126/7 in 2007, 26 million AAV in 2015 dollars age 29, previous 3 yr rWAR10.5,  3 yr avg rWAR 3.5, 2015 AAV/WAR 7.4 mil
 
 
FWIW John Lackey 82.5/5 in 2010 , 21 mil AAV in 2015  age 31 previous 3 yr rWAR 8.6,  3 yr avg rWAR 2.9, 2015 AAV/WAR 7.2 mil
Jon Lester   130/6, 22 mil AAV in 2015 age 31 previous 3 yr rWAR 8.3,  3 yr avg rWAR 2.8, 2015 AAV/WAR 7.8
 
 
Basically the Red Sox are offering Lester 1 extra yr of Lackey money.  Lackey of course had known elbow issues that had the Red Sox put in an injury clause while Lester has been a work horse and injury free  Lester had a much better contract year but basically a similar 3 yr average rWAR
 
No real good comps of the other pitchers except in terms of age.  Lester is 1 yr younger than Cliff Lee but did not pitch as well over the previous 3.  Adjusted AAV is well below Lees (28 vs 22) but AAV/3 yr WAR is much higher.  Of course, maybe the 3 yr average is unfair to Lester, as more weight should probaby be given to his last year which was a 4.6 rWAR, but thats still lower than Lee's 3 yr average.
 
Greinke is probably the best comp in terms of previous 3 yr performance but Greinke was 2 years younger
 
Red Sox have a fair offer on the table, and using Greinke as a comp 25 million AAV might not be crazy, but thats an upper limit.  If he can do better elsewhere, let him.  Other pitchers are available.

 

[lxt]

 
 
It wasn't $110/6 a month ago.  In the original Lester thread, the second post, on August 3rd, MakMan said $130 million, and that's where we are.
 
 
And can the "I'd suggest alternatives..." claptrap, it has no place on the main board.

I was talking about the most recent discussions concerning resigning Lester. I'm not surprise MakMan was right last August. IMO offering Lester 6/$120 back then would likely not have us in our current position. "Claptrap" what a wonderful word. I was just trying to say that this is not the place to be throwing out alternatives as there are other places to do that. Thanks for the input on MakMan's original statement ... in hindsight it was a great prediction.

 

[BarrettsHiddenBall]

Thanks for breaking that down grim! Only quibble is that I'd expect inflation over the life of the contract makes up to 150 doable. You'll probably be overpaying by the end, but not by all that much on a WAR/cash basis.

 

[DukeSox]

Thanks for breaking that down grim! Only quibble is that I'd expect inflation over the life of the contract makes up to 150 doable. You'll probably be overpaying by the end, but not by all that much on a WAR/cash basis.

How much inflation has there been the past 6 years?  Do you expect inflation to increase significantly the next 6?
 
Or do you mean wage inflation among ballplayers?  

 

[SoxFanForsyth]

https://twitter.com/mibeltrodriguez/status/539596458585227265

If he wants 6/150, give the guy 6/150. If you're willing to go to 6/140, don't spend 190mm on Hanley and Panda and skimp on 10mm for your ace

 

[MakMan44]

If that report is to believed, yeah, I can't see drawing the line at 6/140 as being particularly smart. 

 

[Snodgrass'Muff]

The report doesn't say 6/150 means he'll sign immediately without checking to see if another team will top or match it. If the Red Sox aren't confident that offering 6/150 would end it right now, then upping their offer doesn't make a ton of sense.

 

[Bob Montgomerys Helmet Hat]

If he wants 6/150, give the guy 6/150. If you're willing to go to 6/140, don't spend 190mm on Hanley and Panda and skimp on 10mm for your ace

Unless they value him at $120-$130 million, in which case they'd already be stretching if they go to $140.  Regardless, they aren't skimping.

 

[SoxFanForsyth]

Unless they value him at $120-$130 million, in which case they'd already be stretching if they go to $140.  Regardless, they aren't skimping.

If they are willing to stretch to 140, and the alternative is dishing a Betts to get Hamels, then you go the extra 10

 

[Cellar-Door]

https://twitter.com/mibeltrodriguez/status/539596458585227265

If he wants 6/150, give the guy 6/150. If you're willing to go to 6/140, don't spend 190mm on Hanley and Panda and skimp on 10mm for your ace

I doubt he's still the ace at age 37. I'd guess they'd be more than willing to give him $25M a year if he took less years.
I have a lot more faith in position players holding up for longer term deals than pitchers, and both those guys got 5 years.
 
Edit- To reply to the above that got posted while I was writing.
The alternative isn't trading Betts for Hamels. There are many options, including Hamels (which I can't see any way involving Betts). Sacrificing future years for this one isn't something the franchise has shown much desire to do.

 

[catomatic]

I doubt he's still the ace at age 37. I'd guess they'd be more than willing to give him $25M a year if he took less years.
I have a lot more faith in position players holding up for longer term deals than pitchers, and both those guys got 5 years.

The logic of spending what it takes for him—after backing up the truck for Sandoval/Ramirez—seems very rational, but there's a little voice in my head from an unnamed GM who might ask; "If you had $340M dollars to spend, is this how you would do it?" 

 

[SoxFanForsyth]

Can anyone translate this? Google translate was worthless.

https://twitter.com/juniorpepen/status/539605675933196288

 

[rodderick]

Can anyone translate this? Google translate was worthless.


https://twitter.com/juniorpepen/status/539605675933196288
link to tweet

Red Sox are pondering possible trades to bring pitchers into the fold if they don't reach an agreement with Lester.

 

[Fireball Fred]

If we believe the Sox need top-of-the-rotation pitching, there just aren't many options. Pay for Lester, pay more for Scherzer, overpay for Shields, trade for Hamels - those are possibilities. It's telling that there's so much chatter about Samardjiza, who hasn't shown he's more than a #3.

 

[Savin Hillbilly]

I doubt he's still the ace at age 37.

 
Then it's a good thing a six-year deal only pays him through age 36.
 
But I agree that if it takes 6/150--certainly if takes more than 6/150--then a deal for Hamels starts to look like a valid alternative as long as the prospect package does not include Betts, Bogaerts or Swihart.

 

[Bob Montgomerys Helmet Hat]

If they are willing to stretch to 140, and the alternative is dishing a Betts to get Hamels, then you go the extra 10

No, you set a value, you set a range, and then you move on to Plan B when this is exceeded.  And there is less than a 0% chance that Plan B is Betts for Hamels, although it may be a realistic trade for Hamels.

 

[SoxFanForsyth]

No, you set a value, you set a range, and then you move on to Plan B when this is exceeded.  And there is less than a 0% chance that Plan B is Betts for Hamels, although it may be a realistic trade for Hamels.[/quote

My problem is that if you don't get Lester, Hamels requires Betts, or you go with a Samardzija - Shields or Shields - Santana, that's not enough to win in this division this year. So you back up the Brinks truck for Hanley and Sandoval, but you come up 8 or 10mm over 6 years short in Lester, and it essentially wrecks your 2015.

I think you either go with Lester or Hamels to lead this staff. Once Lester is off the board, Hamels price isn't going to come down either

 

[MakMan44]

No, you set a value, you set a range, and then you move on to Plan B when this is exceeded.  And there is less than a 0% chance that Plan B is Betts for Hamels, although it may be a realistic trade for Hamels.[/quote

My problem is that if you don't get Lester, Hamels requires Betts, or you go with a Samardzija - Shields or Shields - Santana, that's not enough to win in this division this year. So you back up the Brinks truck for Hanley and Sandoval, but you come up 8 or 10mm over 6 years short in Lester, and it essentially wrecks your 2015.

I think you either go with Lester or Hamels to lead this staff. Once Lester is off the board, Hamels price isn't going to come down either

You keep saying Hamels requires Betts, but you don't know if that's true. Shark is also probably good enough to lead the rotation, and if you add Shields or Santana as a #2, that's actually probably enough to seriously compete for the division. The Blue Jays are scary, but the rest of the division is completely in flux. We'll see how things shake out, but I would be completely satisfied with a Shark-Shields(Santana)-Buch-Kelly-RDLR(Webster) rotation.  
 
EDIT: And on the Blue Jays, it's not their rotation is all that great right now either. 

 

[DeJesus Built My Hotrod]

Lester's exact average over the past 6 years is 5 WAR per season.  If one win is 6mill or so, I can see the breakdown being something like this which includes a half win of decline per year as he exits his prime.  This also assumes near perfect health like he has had.
5, = 30
4.5, = 27
4. = 24
3.5, = 21
3, = 18
2.5 = 15
= 135
 
Steamer projects him at 3.5 which is a huge drop and seems really conservative to me.  The value of a win may be closer to 7mill though and/or offers could include 5% inflation as well, so this is where I see the bidding going up closer to 150.
 
I haven't been a fan of 6 years for a 30+ pitcher and would rather they spend 4 years on Shields, trade for Fister and sign Miller and maybe Gregorson if they move out of the Lester sweepstakes.  The chance of him remaining healthy over the next years (not even just arm/shoulder injuries)  just seems like the exception at the ages he'll be pitching through.  They don't even have to spend the money.  There's nothing that says they have to approach the luxury tax to field a very good team.

This is a pretty good breakdown of how teams might try to value Lester and I would argue the $7mm per win is probably a fair market these days.  Big market sports teams - and Chicago is clearly a large market - are more inclined to pay up given the value of live sports.  In short, live sports are one of the few events that "bring the boys to the yard" in the sense that people will watch in real time, commercials and all.  Furthermore, a team like the Cubs aren't yet a destination and those teams either have to pay a premium to sign talent or trade for it.  I would be surprised if Lester doesn't get his $150mm and perhaps a bit more when its all said and done.   I, for one, hope the Sox aren't the ones paying that money.

 

[semsox]

At what point does the aversion to the 7th year outweigh the amount given out over 6 years. If they think they're eventually willing to go 6/150, why wouldn't they throw out a 7/155? It would still be a significant step-up from the 6/130 they reportedly have on the table now.  

 

[Hee Sox Choi]

It's telling that there's so much chatter about Samardjiza, who hasn't shown he's more than a #3.

Not true.  KienickedintheHead (or whatever his name is) dropped some stats on everyone's head recently that showed Samardzija has had the 14th best xFIP or FIP the past 3 years.  I can't find the post, but the stats show that he's a borderline ace.  I'll try to find it.  Shark is being underrated.  
 
OK, found it.  From kieckeredinthehead
 
SAMARDZIJA:
xFIP rank last three years, 11th, 22nd, 14th; xFIP rank, mean of last three years: 15th. That puts him a little better than Cole Hamels and a little worse than Madison Bumgarner.

 

[The Boomer]

Red Sox are pondering possible trades to bring pitchers into the fold if they don't reach an agreement with Lester.

 
Theo's possible willingness to overpay the market, like the Nationals did with Jayson Werth a few winters ago, is the price that unproven non-contending teams must pay to make a splash in free agency.  The Werth premium worked out just fine for the Nationals once their farm system rounded out their pitching and lineup. The Cubs have the money.  While maybe a year or two away, it is foreseeable that their farm system will have produced one of if not the best homegrown every day lineups in the game.  This is likely to be the case in years 4-7 of a Lester contract.  While John Henry probably sincerely expressed a willingness to make an exception from their free agent parameters for Lester, the Cubs might be determined to overpay that $150 million for 7 years because this is what it will cost for them to get him.  Unlike the Cubs, who have lots of just emerging cost controlled youngsters during the probable length of a Lester contract, the Red Sox have their share of these too except that they already also paid premiums for Pedroia, Castillo, Hanley and Panda and, short term, for Papi, Cespedes and Napoli.  Don't forget that, despite the 2013 dream year, the Sox really weren't any better last year than the Cubs.  Despite the cost in talent, if Cherington is able to deal from depth in the system, trades for pitchers could end up as a more productive strategy.

 

[moondog80]

No, you set a value, you set a range, and then you move on to Plan B when this is exceeded.

Right. Still plenty of other fish out there. Give your best offer, and move on if it not enough.

 

[InsideTheParker]

Weird, I thought money wasn't important to him.

I think they've already offered too much; time to move on to Plan B.

 
That would be my vote. The longer this takes the more I think about how frustrating it was to watch him pitch a lot of the time. What's to keep him from reverting to the guy who pouts over the calls and forgets how to throw to first base? 

 

[geoduck no quahog]

Just re-stating the obvious, but - if the Red Sox don't fill one or more of their pitching holes with a free agent (any free agent), that means they need to expend more treasure in quality minor league prospects + an outfielder (and/or Kelly) to fill those holes. Plan B needs to include a FA, otherwise they need to deal more potentially great and cheap talent for at least 2 (maybe 3) starters and a decent, proven reliever.
 
I don't see how they can fill all the holes without free agency. If they do, it's probably something like Hamels, Latos, Samardzija, Buccholz, De La Rosa with the bullpen we have today. (Don't hold me to those names, just throwing an example out there). 
 
In that example, those 3 cost Cespedes or Betts, Kelly, and pick several highly ranked minor leaguers (depending on whether or not Betts is needed for a trade).
 
Knocking one of those holes off through free agency dramatically improves the trading position for other holes. (I said I was re-stating the obvious)

 

[JohntheBaptist]

 
That would be my vote. The longer this takes the more I think about how frustrating it was to watch him pitch a lot of the time. What's to keep him from reverting to the guy who pouts over the calls and forgets how to throw to first base? 

 
Wow, well I'm convinced.

 

[DeJesus Built My Hotrod]

At what point does the aversion to the 7th year outweigh the amount given out over 6 years. If they think they're eventually willing to go 6/150, why wouldn't they throw out a 7/155? It would still be a significant step-up from the 6/130 they reportedly have on the table now.  

 
Because Lester's agent would then ask for 7/$160mm.  Good negotiators don't typically go beyond the minimum amount they think it will take to get a deal done - you start low and go higher until you get the deal done or get stopped out.   Plus, seven years for a 31 year old pitcher who has thrown 1,600 innings in the majors and almost 500 more in the minors is a huge risk.  I am surprised the Sox are willing to go six years on a pitcher with that kind of milage to begin with - regardless of how great Lester has been over the past few years, he is a fair bet to decline half-way through the contract.  $20mm+ for a guy who may not even be pitching for your team is painful (even in 2020 dollars), especially if its for multiple seasons.

 

[Plympton91]

I hear you, and I wouldn't crucify the Sox' FO if they did just that.

SO LONG AS they didn't then go out and spend more on Scherzer or make a stupid deal for Hamels, etc. if they went the alternative route you and I suggest then I'd be fine with that.

Put me down for this too. If they don't want to pay for an ace, fine. Go sign McCarthy and two more like him. But I better not see Lester go somewhere else and then Betts traded for Hamels.

 

[URI]

This thread is for Jon Lester.
 
If you are determined to talk about Chris Sale, start a new thread.

 

[LahoudOrBillyC]

The Red Sox can win 90 games next year without Jon Lester. They have a ton of money that they could spend on a few other pitchers.

I would move on.

 

[Plympton91]

You know what would really suck; if John Lester ends up signing with the Giants because the Red Sox signed Pablo Sandoval. Rotisserie league baseball increasingly mimics real life. Is it any wonder some people just check out and do something else on all those beautiful summer nights we spend glued to a TV screen?

 

[BeantownIdaho]

Yankees sweep in at 6/155

 

[URI]

Yankees sweep in at 6/155

 
This isn't a game thread, or a chatroom.
 
Add content or don't post.

 

[Montana Fan]

The Red Sox can win 90 games next year without Jon Lester. They have a ton of money that they could spend on a few other pitchers.

I would move on.

Lahoud, real glad to see your posts around the board. Would like to see how the Sox would get to 90 wins without Lester and who you think they should target as I believe they need 2 starters. I'll be waiting over on the Trading for Starting Pitchers to read your thoughts.

 

[soxhop411]

I was going through my iPhones library and came across this video I recorded of MLBN the day after we traded Lester....  Sox players were saying that they had a good feeling they would be playing with Lester again
 
 
https://www.youtube.com/watch?v=VOXmxkNG5Gc

 

[koufax37]

Lester wants to be back here, but Chicago and San Francisco are really appealing landing places, and we have to see what the MFY do.
 
I genuinely believe it isn't about the money, and he understands he will have more than he can spends.  That doesn't mean money is disregarded in similarly appealing situations.  I can't see him going to the Yankees even for more money, but can easily see him taking Chicago, SF, or (before it was ruled out) Atlanta's money.
 
Right now everybody is worried because we have nine outfielders, no pitchers, and seven billion dollars of John Henry's money that they don't mind becoming Jon Lester's money.  But overpaying him (a value TBD) doesn't make any sense, and hurts our financial flexibility.  I think there is a fair chance we are in a bubble in TV deals, and the salary spiral cools off.  If year four or five of an overpaid Lester keeps us from being competitive on a more valuable piece of our team, we have hurt our overall chances.  I think 6/144 is pushing it, and there is a point where you have to stop raising your paddle.  It isn't about the final $2M, it is that valuing him at the first $23M was already a big leap of faith.
 
As for the thoughts that we should have wrapped him up before the season, I personally was still worried about the course he was on, and if the 2013 playoffs or 2012 season was a better indicator of who he would be, and I think the extra dollars we are paying if we end up signing him are actually a reasonable tradeoff for both Cespedes (and his trade value) and increased certainty through a full 2014 season of him demonstrating health, focus, and competence.
 
I look forward to hearing the good news when his signing is announced, but if Theo or the Giants go beyond what is reasonable then we shouldn't hurt our ability to build a competitive team by locking up an unreasonable share of our resources in a specific player relative to his value.
 
There are a million ways to build out a rotation, especially when you have payroll flexibility, major league caliber power hitters and a lot of prospects.  I think Ben is smart enough to have some creative alternatives to just Lester/Scherzer/Hamels and won't lock in to one option if the price isn't right.

 

[BarrettsHiddenBall]

How much inflation has there been the past 6 years?  Do you expect inflation to increase significantly the next 6?
 
Or do you mean wage inflation among ballplayers?  

Baseball. Just depends how long the TV money bubble lasts.

 

[MikeM]

 
 Plus, seven years for a 31 year old pitcher who has thrown 1,600 innings in the majors and almost 500 more in the minors is a huge risk.  I am surprised the Sox are willing to go six years on a pitcher with that kind of milage to begin with - regardless of how great Lester has been over the past few years, he is a fair bet to decline half-way through the contract.  $20mm+ for a guy who may not even be pitching for your team is painful (even in 2020 dollars), especially if its for multiple seasons.

 
This is pretty much where my head is at.
 
Last year was frustrating, but i still find it hard to swallow the overall concept that a "get an on paper ace at all costs" approach to this off season is really that much of an absolute make-or-break necessity. Especially following a year that saw Baltimore win the division. The AL East landscape isn't quite the bankable scenario it used to be imo. 
 
It's also not like we went into this winter looking at a roster construction that was a Jon Lester away from winning it all last year. As others here have pointed out, there is more then one way to build a good team for 2015 and going forward. If 6/$150m is really what it takes, i'd wish him the best of luck in Chicago next season.