Let's Talk Exten$ions...

Sep 13, 2006
689
The (once-again) agonizingly slow marketplace for high-end free agents, coupled with the Sox having numerous key players with the ability to test next offseason's market makes this a fascinating period to ponder if any extensions will get done now or during the season.

There's also the fact that the Sox are currently very close to exceeding the highest tier of the Competive Balance Tax. Any extension(s) would (without a corresponding move to shed salary elsewhere) undoubtedly push them over the threshold.

As of today, we have Tom Werner publicly stating that the Sox have engaged in extension talks with Sale. https://www.google.com/amp/s/nesn.com/2019/02/red-sox-have-had-extension-talks-with-chris-sale-but-striking-deal-not-easy/amp/

Bogaerts has expressed an interest in an extension: Pending free agent Bogaerts open to extension

As has the Brockstar: https://weei.radio.com/blogs/rob-bradford/potential-free-agent-be-brock-holt-i-want-be-boston-forever

I thought it might be useful to have a separate thread for discussions on this particular topic.
 
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keninten

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Nov 24, 2005
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The (once-again) agonizingly slow marketplace for high-end free agents, coupled with the Sox having numerous key players with the ability to test next offseason's market makes this a fascinating period to ponder if any extensions will get done now or during the season.

There's also the fact that the Sox are currently very close to exceeding the highest tier of the Competive Balance Tax. Any extension(s) would (without a corresponding move to shed salary elsewhere) undoubtedly push them over the threshold.

As of today, we have Tom Werner publicly stating that the Sox have engaged in extension talks with Sale. https://www.google.com/amp/s/nesn.com/2019/02/red-sox-have-had-extension-talks-with-chris-sale-but-striking-deal-not-easy/amp/

Bogaerts has expressed an interest in an extension: Pending free agent Bogaerts open to extension

As has the Brockstar: https://weei.radio.com/blogs/rob-bradford/potential-free-agent-be-brock-holt-i-want-be-boston-forever

I thought it might be useful to have a separate thread for discussions on this particular topic.
An extension will effect the CBT but is their a time in the season where it will not? If a player is making $5 mil this year and signs an extension for $40 mil for 4 years. His average is now at $9 mil a year. Is there anything in the CBT that changes as the year progresses? I know it changed in the last agreement. Otherwise I`ve never thought the Sox would be offering extensions because of the new agreement. I hope I`m getting my point across. This is why I post little. Have trouble getting my thoughts on paper.
 

Hank Scorpio

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I’m of the mind that:

1: By the time the next CBA comes around, we’re likely to see a sizable increase in luxury tax thresholds or a reduction in penalties for exceeding the threshold. Probably a combination of both.

2: While the penalties are currently severe, having talents like Sale and Betts (especially Betts) far outweigh those penalties.

3: Sale on a long term deal, however, is worrying considering his shoulder woes last season. There might be better options.

4: Keep Mookie, no matter the cost.
 

koufax32

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Any extension for a 31 year old Sale (2020) that was more than 2 years would make me extremely uncomfortable. I’d really like to know what time frame he’s thinking.
 

RedOctober3829

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Any extension for a 31 year old Sale (2020) that was more than 2 years would make me extremely uncomfortable. I’d really like to know what time frame he’s thinking.
31 years old is not that old. If he was going to be 33 or 34 and talking a big extension that's one thing. A 4 year extension for a 31 year old Sale is not that huge of a risk. With the free agent market being what it is, Sale may be smart in taking an extension now anyways.
 

Red(s)HawksFan

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An extension will effect the CBT but is their a time in the season where it will not? If a player is making $5 mil this year and signs an extension for $40 mil for 4 years. His average is now at $9 mil a year. Is there anything in the CBT that changes as the year progresses? I know it changed in the last agreement. Otherwise I`ve never thought the Sox would be offering extensions because of the new agreement. I hope I`m getting my point across. This is why I post little. Have trouble getting my thoughts on paper.
You got your point across very well. I don't believe there's any deadline after which extensions no longer apply to the current season. The current CBA did away with that sort of thing (specifically the old deadline of Opening Day). If the deal is officially struck during the fiscal year, it applies to that fiscal year.

That said, there's nothing prohibiting teams and players from agreeing to an extension and not technically signing it until the day after the season ends. Same as used to happen with the Opening Day gambit (Adrian Gonzalez being a prominent example). Of course, if both sides agree to wait until after the season to sign it, there's no real incentive to negotiate until that point either. Injuries could change things. So could having a monster season.
 

moondog80

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31 years old is not that old. If he was going to be 33 or 34 and talking a big extension that's one thing. A 4 year extension for a 31 year old Sale is not that huge of a risk. With the free agent market being what it is, Sale may be smart in taking an extension now anyways.
His arm seems like a time bomb, just like Pedro's did. The treated him with kid gloves in September two years in a row and he was subpar in the postseason both times. Even at 4 years, let someone else take the risk and use the $ elsewhere. I actually thought when they re-signed Eovaldi it meant they knew they would let Sale walk.
 

RedOctober3829

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His arm seems like a time bomb, just like Pedro's did. The treated him with kid gloves in September two years in a row and he was subpar in the postseason both times. Even at 4 years, let someone else take the risk and use the $ elsewhere. I actually thought when they re-signed Eovaldi it meant they knew they would let Sale walk.
From age 30 to 33, Pedro pitched 30, 29, 33, and 31 starts. He was over 200 innings at age 32 and 33. At age 34, it dropped to 23 starts then after that the Pedro we knew was over.

With Sale, I get why you would be hesitant because I would be too. I've said as much. I just think that what he gives a team from April to August-early September is worth the risk of him losing some steam come the rest of September. Where are they using the money to provide what Sale has done? Not many starting pitchers of his caliber are reaching free agency.
 

nvalvo

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An extension will effect the CBT but is their a time in the season where it will not? If a player is making $5 mil this year and signs an extension for $40 mil for 4 years. His average is now at $9 mil a year. Is there anything in the CBT that changes as the year progresses? I know it changed in the last agreement. Otherwise I`ve never thought the Sox would be offering extensions because of the new agreement. I hope I`m getting my point across. This is why I post little. Have trouble getting my thoughts on paper.
I think I followed what you were saying.

The short answer is not anymore. Theo manipulated that with the Adrian Gonzalez extension, and the next CBA tightened that up. The AAVs are now prorated.

Notwithstanding the foregoing, if a Multi-Year Contract is signed after Opening Day of the championship season, the: (i) Base Salary in the first Guaranteed Year for purposes of the AAV calculation shall be determined by multiplying that Base Salary by a fraction, the numerator of which shall be the number of championship season days that the Player was paid the Base Salary, and the denominator shall be the number of championship season days in that championship season
That's from the CBA: Article XXIII.E.2.
 

Dewey'sCannon

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Jul 18, 2005
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I don't think the CBT penalties in 2019 will stand in the way of an agreement on an extension that they would otherwise make with any of these players.

Sale is an interesting case - high risk/high reward. Of he's looking for $30m AAV for 4 or 5 years on an extension, that would give me pause, but 25/4 I might jump at. You could wait and see how things work out this year, but if he's healthy and has a good year then the price probably goes up at at least 30.

I wonder what Xander's price would be. With Boras as his agent, I don't think there'll be any hometown discount. But I'd love to be able to lock him up now.
 

nvalvo

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He had one goal: to strengthen his shoulder.

“I was basically working on the brakes,” Sale said. “Last year that’s what got me. My arm was moving fast, but I didn’t have the strength or the muscle capacity to slow it down.”
I saw this in an article at the Athletic. I’ve never heard of that shoulder issue. Any insight?
 

Papelbon's Poutine

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His arm seems like a time bomb, just like Pedro's did. The treated him with kid gloves in September two years in a row and he was subpar in the postseason both times. Even at 4 years, let someone else take the risk and use the $ elsewhere. I actually thought when they re-signed Eovaldi it meant they knew they would let Sale walk.
If the Sox are talking extension with him, I’m confident they think the medicals look okay or if they don’t, they’d be getting a discount. Sign him up.
 
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Red(s)HawksFan

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I saw this in an article at the Athletic. I’ve never heard of that shoulder issue. Any insight?
I'm not a doctor, but it makes sense to me. He definitely did something mid-season that accelerated his fastball...new motion, new angle, whatever it was, he was throwing harder. I can see where the strain from that could come from trying to stop his arm after the throw. It's not something that you consider until it hurts.

If he's identified the issue and taken steps to strengthen the right muscles so that he can go back to that free and easy 99 he was throwing in June and July without risk of more inflammation, sign him up now.
 

moondog80

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If the Sox are talking extension with him, I’m confident they think the medicals look okay or if they don’t, they’d be getting a discount. Sign him up.

You're right that they have more info than I do, and they're just generally better at this than I am, but that doesn't mean they are infallible. I mean, the logical extension of this is they we simply shouldn't question any move they make, ever. Which, at the very least, would make for a very boring message board.

The devil is in the details of course, but it if turns out they bring him him back at the expense of losing Bogaerts or Betts (assuming all three end up signing in the range of what would be expected), I think that will be the wrong move.
 

Minneapolis Millers

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...The devil is in the details of course, but it if turns out they bring him him back at the expense of losing Bogaerts or Betts (assuming all three end up signing in the range of what would be expected), I think that will be the wrong move.
Next year things get really interesting. Looking at Cots, we will have a ton of $$$ being freed up with Porcello, Sale, Sandoval, X, Moreland, Nunez, Pence, Holt, and Thornburg all FAs. That's around $85M. Plus $22M more if JDM opts out. With $100M+ they certainly could re-up at or near expected market rates for Sale, Betts and X. But they'd still need to replace a ton of talent. It would help if Pedroia returns healthy, someone like Chavis becomes a reliable contributor, 2-3 young cheap bullpen arms emerge, and E-Rod puts up 200 innings as a #2 quality starter. And maybe JDM stays or they negotiate a small bump to keep him here and happy.
 
Sep 13, 2006
689
And maybe JDM stays or they negotiate a small bump to keep him here and happy.
Speaking of JD, per the article linked below: "Werner said on WEEI on Monday that the team has not had discussions with Martinez about working out a new deal."

If JD has a 2019 season that reasonably approximates his 2018 work, Boras is extremely likely to be looking for much more than a "small bump" and the negotiations are likely to drag onnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn.

https://www.mlb.com/news/2018-2019-mlb-free-agents-and-trade-rumors/c-297641124
 

Dewey'sCannon

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So what do we think an extension for Bogaerts would look like? If he has another good year, his price probably goes up, but Boras is unlikely to give much of a discount for signing a year early, unless he's also bumping up his money for the current year through either salary or a signing bonus.

Bogey avoided arb and agreed to 12m for 2019, up from the 7.05m he made last year. I did a quick search for salaries for other shortstops:
Elvis Andrus - in the fifth year of an 8/120 deal - 15m AAV. Carries through age 33 season
Jean Segura - in year 2 of a 5/70 extension he signed in June 2017, making 14.25 in 2019-22 (then 32)
Brandon Crawford - making 15.2 in year 4 of a 6/75 deal (through age 34)
Didi Gregorious - 11.75 in his final arb year (age 29)
Lindor - 10.55 in Arb1 at age 25 (FA 2022)

https://www.spotrac.com/mlb/contracts/shortstop/

So maybe something in the 15-17 AAV range would get it done. But for how many years? Xander turns 27 on Oct. 1 this year. My bet is that Boras would be looking for 8-10 years (at least through age 34). I'd probably be ok with 7 or 8, but could see some combination of option year, opt outs or "swell-opts" after year five or six that could push it to 10 years if the Sox pick them up.

Thoughts?
 
Sep 13, 2006
689
...So maybe something in the 15-17 AAV range would get it done. But for how many years? Xander turns 27 on Oct. 1 this year. My bet is that Boras would be looking for 8-10 years (at least through age 34). I'd probably be ok with 7 or 8, but could see some combination of option year, opt outs or "swell-opts" after year five or six that could push it to 10 years if the Sox pick them up.

Thoughts?
With Machado just signing for $300M/10 years, I can't envision Boras looking for anything less than $25M/year for 7 years for X.

 

In my lifetime

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With Machado just signing for $300M/10 years, I can't envision Boras looking for anything less than $25M/year for 7 years for X.

And after Harper signs for similar, at least we should stop hearing about the calls for a work stoppage.

But the RS have big contracts and a lot of decisions starting next year:
Some guesses
Betts 10/320
X. 7/150
Sale 5/145
JD 4/100

That's an AAV of over 105MM for those 4. Of course, a lot will depend on their 2019 performance.

And if they manage to keep those 4, you would think Porcello, Nunez, Moreland/Pearce would all have to be replaced with much less expensive options. And it's also easy to see why the RS lack interest in any top line closer who would command more than 1 year contract at significant AAV.
 
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PrometheusWakefield

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So what do we think an extension for Bogaerts would look like? If he has another good year, his price probably goes up, but Boras is unlikely to give much of a discount for signing a year early, unless he's also bumping up his money for the current year through either salary or a signing bonus.

Bogey avoided arb and agreed to 12m for 2019, up from the 7.05m he made last year. I did a quick search for salaries for other shortstops:
Elvis Andrus - in the fifth year of an 8/120 deal - 15m AAV. Carries through age 33 season
Jean Segura - in year 2 of a 5/70 extension he signed in June 2017, making 14.25 in 2019-22 (then 32)
Brandon Crawford - making 15.2 in year 4 of a 6/75 deal (through age 34)
Didi Gregorious - 11.75 in his final arb year (age 29)
Lindor - 10.55 in Arb1 at age 25 (FA 2022)

https://www.spotrac.com/mlb/contracts/shortstop/

So maybe something in the 15-17 AAV range would get it done. But for how many years? Xander turns 27 on Oct. 1 this year. My bet is that Boras would be looking for 8-10 years (at least through age 34). I'd probably be ok with 7 or 8, but could see some combination of option year, opt outs or "swell-opts" after year five or six that could push it to 10 years if the Sox pick them up.

Thoughts?
Way more than any of those.

Andrus extension was unique and 4 years ago, Lindor and Gregorius aren't FAs, Crawford is not as good a player and way older when he signed in 2016.

If Bogaerts was a FA this year, his 4.9 WAR would have ranked third among FAs behind Machado and Corbin, which Fangraphs estimates at $39m in value.

If we assume that Bogaerts regresses to his 4 year average 4.375 WAR through his age 29 season, and then declines 0.5 WAR each year after that, then over a seven year period from 2020-2026 he could be expected to put up 25.6 WAR.

At Fangraphs current dollars per WAR calculation - $7.9 million without inflation - that makes him worth $203 million on a 7 year deal. Add 5% inflation during the period (if you think salaries are actually going to start rising again) and that goes up to $244 million. Throw in an eighth year and it's $218 without inflation or $266 with inflation.

Bogaerts is a stud free agent any way you look at it. He ain't going for Elvis Andrus money.

EDIT:

On the other hand, if I run the same system for Machado (taking his average 5.4 WAR, assuming steady state through age-29 and then declining 0.5 WAR each year after that) then I get 43.75 WAR for $300m, or $6.85m/WAR.

If that's the value of a WAR in free agency these days then the 7 year projected price for Bogaerts would fall to $175m or 8 years for $188m.

Of course, there could be value to the opt-out, especially if the Padres front loaded the contract the way they did for Hosmer.
 
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Al Zarilla

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Next year things get really interesting. Looking at Cots, we will have a ton of $$$ being freed up with Porcello, Sale, Sandoval, X, Moreland, Nunez, Pence, Holt, and Thornburg all FAs. That's around $85M. Plus $22M more if JDM opts out. With $100M+ they certainly could re-up at or near expected market rates for Sale, Betts and X. But they'd still need to replace a ton of talent. It would help if Pedroia returns healthy, someone like Chavis becomes a reliable contributor, 2-3 young cheap bullpen arms emerge, and E-Rod puts up 200 innings as a #2 quality starter. And maybe JDM stays or they negotiate a small bump to keep him here and happy.
And after Harper signs for similar, at least we should stop hearing about the calls for a work stoppage.

But the RS have big contracts and a lot of decisions starting next year:
Some guesses
Betts 10/320
X. 7/150
Sale 5/145
JD 4/100

That's an AAV of over 105MM for those 4. Of course, a lot will depend on their 2019 performance.

And if they manage to keep those 4, you would think Porcello, Nunez, Moreland/Pence would all have to be replaced with much less expensive options. And it's also easy to see why the RS lack interest in any top line closer who would command more than 1 year contract at significant AAV.
Two people telling me all time fave Giant Hunter Pence plays for the Red Sox now?
 

PrometheusWakefield

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OK, what the hell, lets do everybody else the same way.

I used Steamer projections for next year as a baseline, assumed steady state through age 29 and then 0.5 WAR/year decline after that. I then multiplied by Fangraph's estimate of $7.9m/win, and then also took a look at the $6.85m/win suggested by the Machado deal (although again we don't have the details yet to determine the actual value of the opt-out). I also made arbitrary assumptions about contract length. Here's what I got:

Sale (after 2019): 6 years, 31.5 WAR. $248m in value from Fangraphs, $216 based on Machado signing. AAV between $36m and $42m.
Betts (after 2020): 10 years, 54 WAR. $426m in value from Fangraphs, $370m based on Machado signing. So AAV between $37m and $43m.
Bogaerts (after 2019): 7 years, 25.6 WAR. $202m in value from Fangraphs, $175 Machado level. AAV between $25 and $28m.
JDM (after 2019): 5 years, 10.5 WAR. $83m Fangraphs value, $72m Machado value. AAV between $14.3m and $16.6m.
JBJ: (after 2020) 3 years, 5.4 WAR. $43m Fangraphs value, $37m Machado value. AAV between $9m and $10m.
Porcello (after 2019): 4 years, 5 WAR. $40m Fangraphs vaue, $34m Machado value. AAV between $8m and $9m.
 

PrometheusWakefield

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So thinking about what this means for my goal of keeping as many guys as possible.

Lets say after this year we sign Sale at 6/$240 ($40m AAV) and Bogaerts at 7/189 ($27m AAV), let Porcello walks and JDM declines the opt-out. That would put us at $158m committed for 7 players.

Then lets give Mookie $25m in arbitration, increase Edro's salary to $6m in his A3 year, and give JBJ $10m in his final year of arbitration, give Benintendi $4m for his first year of arb and $2m each to the relievers: Barnes, Wright, Hembree and Workman, as well as either Swihart or Leon. That's another $55m for 9 players, or $211 for 16 guys. Throw in $5 million for Pablo Sandoval's remaining opt-out and it puts us at $216m.

If we are trying to maintain 2019 levels, that would give us potentially $21 million to play with for the other 9 spots - including first base (Pearce/Moreland or replacement), the bullpen and replacements for Holt and Nunez. Difficult, but not impossible.

In 2021, the big task is obviously resigning Mookie, at something like 10/400. Then I have JBJ resigning close to his A4 value of $10m AAV. That puts us up to $202m in committed contracts for 9 guys (yikes). Give Edro 8, Benintendi 6 and that's $216m for 11 players.

All of which is to say that looking it over, it is possible to imagine the Red Sox keeping the whole core together - but it will require the team to be extremely economical with the rest of their roster. Players like Holt, Pearce, Moreland, and Nunez would all require internal replacements like Lin, Chavis, maybe Dalbec. It also would require the Red Sox to build a bullpen basically without spending anything on high priced relievers. Presumably that means Brasier, Barnes, Wright and Hembree can hold down the fort this year and guys like Darwinian Hernandez and Tanner Houck turn into real weapons in the pen. And even then, this is all on the assumption that the Sox are prepared to pay the luxury tax penalties basically indefnitely to keep this core together.
 

Plympton91

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One thing about Bogaerts is that there are a lot of good shortstops these days. The market may not be there from the top teams to drive up the price, even if he has a very good year.
 

moondog80

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So thinking about what this means for my goal of keeping as many guys as possible.

Lets say after this year we sign Sale at 6/$240 ($40m AAV) and Bogaerts at 7/189 ($27m AAV), let Porcello walks and JDM declines the opt-out. That would put us at $158m committed for 7 players.

Then lets give Mookie $25m in arbitration, increase Edro's salary to $6m in his A3 year, and give JBJ $10m in his final year of arbitration, give Benintendi $4m for his first year of arb and $2m each to the relievers: Barnes, Wright, Hembree and Workman, as well as either Swihart or Leon. That's another $55m for 9 players, or $211 for 16 guys. Throw in $5 million for Pablo Sandoval's remaining opt-out and it puts us at $216m.

If we are trying to maintain 2019 levels, that would give us potentially $21 million to play with for the other 9 spots - including first base (Pearce/Moreland or replacement), the bullpen and replacements for Holt and Nunez. Difficult, but not impossible.

In 2021, the big task is obviously resigning Mookie, at something like 10/400. Then I have JBJ resigning close to his A4 value of $10m AAV. That puts us up to $202m in committed contracts for 9 guys (yikes). Give Edro 8, Benintendi 6 and that's $216m for 11 players.

All of which is to say that looking it over, it is possible to imagine the Red Sox keeping the whole core together - but it will require the team to be extremely economical with the rest of their roster. Players like Holt, Pearce, Moreland, and Nunez would all require internal replacements like Lin, Chavis, maybe Dalbec. It also would require the Red Sox to build a bullpen basically without spending anything on high priced relievers. Presumably that means Brasier, Barnes, Wright and Hembree can hold down the fort this year and guys like Darwinian Hernandez and Tanner Houck turn into real weapons in the pen. And even then, this is all on the assumption that the Sox are prepared to pay the luxury tax penalties basically indefinitely to keep this core together.
I think you are way overestimating the cost of Betts/Bogaerts/Sale, but I agree with the general premise that keeping all three leaves little to no margin for error with the rest of the roster. If the attitude from ownership is screw it, we'll spend whatever we have to no matter what happens, then of course they should go for it. But in a world where they more or less have to pick two out of the three, Sale is the obvious man out IMO.
 

Papelbon's Poutine

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You're right that they have more info than I do, and they're just generally better at this than I am, but that doesn't mean they are infallible. I mean, the logical extension of this is they we simply shouldn't question any move they make, ever. Which, at the very least, would make for a very boring message board.

The devil is in the details of course, but it if turns out they bring him him back at the expense of losing Bogaerts or Betts (assuming all three end up signing in the range of what would be expected), I think that will be the wrong move.
Of course they’re not infallible and I’m not suggesting it. I’m just saying that though their is risk, they have a lot more info than we do. If they are talking about a sizable extension their doctors are likely confident in his shoulder health. Look, I don’t want them to be tied into a big money deal that turns out to be a waste, but if they’re confident, I think they should do it. Every pitcher runs arm injury risks - it’s not built to throw a baseball - and no, I don’t want to lose X or Mookie, but I’m pretty sure they have a plan.
 

[icon]

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OK, what the hell, lets do everybody else the same way.

I used Steamer projections for next year as a baseline, assumed steady state through age 29 and then 0.5 WAR/year decline after that. I then multiplied by Fangraph's estimate of $7.9m/win, and then also took a look at the $6.85m/win suggested by the Machado deal (although again we don't have the details yet to determine the actual value of the opt-out). I also made arbitrary assumptions about contract length. Here's what I got:

Sale (after 2019): 6 years, 31.5 WAR. $248m in value from Fangraphs, $216 based on Machado signing. AAV between $36m and $42m.
Betts (after 2020): 10 years, 54 WAR. $426m in value from Fangraphs, $370m based on Machado signing. So AAV between $37m and $43m.
Bogaerts (after 2019): 7 years, 25.6 WAR. $202m in value from Fangraphs, $175 Machado level. AAV between $25 and $28m.
JDM (after 2019): 5 years, 10.5 WAR. $83m Fangraphs value, $72m Machado value. AAV between $14.3m and $16.6m.
JBJ: (after 2020) 3 years, 5.4 WAR. $43m Fangraphs value, $37m Machado value. AAV between $9m and $10m.
Porcello (after 2019): 4 years, 5 WAR. $40m Fangraphs vaue, $34m Machado value. AAV between $8m and $9m.
I think we keep 3 of those guys... MAYBE 4....max.
 

RedOctober3829

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So thinking about what this means for my goal of keeping as many guys as possible.

Lets say after this year we sign Sale at 6/$240 ($40m AAV) and Bogaerts at 7/189 ($27m AAV), let Porcello walks and JDM declines the opt-out. That would put us at $158m committed for 7 players.

Then lets give Mookie $25m in arbitration, increase Edro's salary to $6m in his A3 year, and give JBJ $10m in his final year of arbitration, give Benintendi $4m for his first year of arb and $2m each to the relievers: Barnes, Wright, Hembree and Workman, as well as either Swihart or Leon. That's another $55m for 9 players, or $211 for 16 guys. Throw in $5 million for Pablo Sandoval's remaining opt-out and it puts us at $216m.

If we are trying to maintain 2019 levels, that would give us potentially $21 million to play with for the other 9 spots - including first base (Pearce/Moreland or replacement), the bullpen and replacements for Holt and Nunez. Difficult, but not impossible.

In 2021, the big task is obviously resigning Mookie, at something like 10/400. Then I have JBJ resigning close to his A4 value of $10m AAV. That puts us up to $202m in committed contracts for 9 guys (yikes). Give Edro 8, Benintendi 6 and that's $216m for 11 players.

All of which is to say that looking it over, it is possible to imagine the Red Sox keeping the whole core together - but it will require the team to be extremely economical with the rest of their roster. Players like Holt, Pearce, Moreland, and Nunez would all require internal replacements like Lin, Chavis, maybe Dalbec. It also would require the Red Sox to build a bullpen basically without spending anything on high priced relievers. Presumably that means Brasier, Barnes, Wright and Hembree can hold down the fort this year and guys like Darwinian Hernandez and Tanner Houck turn into real weapons in the pen. And even then, this is all on the assumption that the Sox are prepared to pay the luxury tax penalties basically indefnitely to keep this core together.
It will not take $240 million to sign Sale. Patrick Corbin got $144 million. Sale will not eclipse that by almost $100 million. Bogaerts definitely won't get $189 million that is an insane number. He'll be lucky to get $100-$125 million given the free agent market the last couple years and the volume of good shortstops there are. 2 years down the road Correa, Story, Lindor, and Seager all could be FA's.
 

Ed Hillel

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It will not take $240 million to sign Sale. Patrick Corbin got $144 million. Sale will not eclipse that by almost $100 million. Bogaerts definitely won't get $189 million that is an insane number. He'll be lucky to get $100-$125 million given the free agent market the last couple years and the volume of good shortstops there are. 2 years down the road Correa, Story, Lindor, and Seager all could be FA's.
Teams are going to have serious concerns about Sale’s longevity and injury risk, so I’d be surprised if he’s eclipsing 150, barring a dominant 200 IP performance and playoff success. I know I wouldn’t give him that much, even if he’s Pedro this season.
 

Bob Montgomery's Helmet Hat

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It will not take $240 million to sign Sale. Patrick Corbin got $144 million. Sale will not eclipse that by almost $100 million. Bogaerts definitely won't get $189 million that is an insane number. He'll be lucky to get $100-$125 million given the free agent market the last couple years and the volume of good shortstops there are. 2 years down the road Correa, Story, Lindor, and Seager all could be FA's.
You're correct about these two.
I'll add that, as awesome as Mookie is, he ain't getting $100 million more than Manny Machado.
 

Dewey'sCannon

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As evidenced by the hypothetical posted above by PW, $40m/yr is hard to see under the current CBA because of the practical limitations it poses for roster construction - it's really hard to make the math work unless you've got a roster of mostly cost-controlled guys, which never lasts for long. So I agree that his projections of 6/240 for Sale and 7/189 for X are inflated.

I could see Sale getting 5/150 as a FA, if he has dominant year and stays healthy. They should be able to get him for less than that on an extension now. For Bogey, I could see a 7 year deal for somewhere in the 115-120 range (around 17 AAV). I don't see how even Boras could get him more than 20 per on a long-term deal, unless 2019 turns out to be a top 5 MVP season.

If they can make those kind of numbers fit and still afford Mookie, then great. But if not, I agree that Sale is the one to take a pass on.
 

chawson

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It will not take $240 million to sign Sale. Patrick Corbin got $144 million. Sale will not eclipse that by almost $100 million. Bogaerts definitely won't get $189 million that is an insane number. He'll be lucky to get $100-$125 million given the free agent market the last couple years and the volume of good shortstops there are. 2 years down the road Correa, Story, Lindor, and Seager all could be FA's.
It's impossible to guess contract numbers right now, but I'm more inclined to think Bogaerts will hit (or surpass) that figure than I was last month, before Machado netted $300M. If Machado's contract were to dip to the 7/$175M range as some were reporting mid-January, then sure, re-upping Bogaerts somewhere around 80-120 seemed possible. But if he puts up another 5-win season — or even 6-win, a full season at 2018's pace — he'll be a Boras client only nine months older than Machado who has roughly the same offensive production, plays a better shortstop, and comes with none of the baggage, real or perceived. With at least the Yankees, White Sox, and us involved. I think he’ll be paid.

As for Correa, Lindor, Story and Seager, they're all free agents before the 2022 season, so three years down the road.
 
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Dewey'sCannon

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Hicks agreed to $6M for 2019, while JBJ signed for 8.55, so JBJ is working off a significantly higher base (42.5% higher). I think an extension for JBJ would probably be priced about 40% higher as well - so maybe $100M for a 7 year deal (14 AAV vs 10 for Hicks).
 

PrometheusWakefield

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Starting from Steamer estimates of projected WAR in 2019 (JBJ 2.6, Hicks 3.3) and declining 0.5 WAR every year for their 30s, I have Hicks being worth 12.6 wins over the course of the contract against 5.5 wins for JBJ. So a pretty big difference in value. Also Hicks was a FA after 2019, JBJ after 2020. Both factors would suggest a lower salary extension figure for JBJ than Hicks.
 

Average Game James

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ESPN is reporting the Rockies and Arenado are close to finalizing an 8yr/$260mn ($32.5mn AAV) extension. He’s a year older and was set to hit FA after this year, but have to think any talks with Mookie start a bit north of that. Arenado has been a 6-7 WAR player the past 3 years vs. Mookie staking a strong claim as “best player in the MLB not named Trout.” Does 10/$350mn get it done?

Edit: Per Passan, includes opt out after year 3 that would let Arenado hit FA again at age 30 and a full NTC.

 

Hank Scorpio

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ESPN is reporting the Rockies and Arenado are close to finalizing an 8yr/$260mn ($32.5mn AAV) extension. He’s a year older and was set to hit FA after this year, but have to think any talks with Mookie start a bit north of that. Arenado has been a 6-7 WAR player the past 3 years vs. Mookie staking a strong claim as “best player in the MLB not named Trout.” Does 10/$350mn get it done?
In 2017, Mookie had an “off year”, and was still a 6.5 WAR player.

I’d take him at 10/350 in a heartbeat.