Revised contract predictions for Snell and Montgomery

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BaseballJones

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Is it that simple, though? A 3/75 contract from Texas would keep more money in Monty's pocket than the same contract from Boston, and every indicator I see tells me he'd rather be there, even if all things were equal. How much of a premium do you think would be reasonable in that case? What if the hypothetical 3/75 contract has an opt out after year one?

I won't be pissed simply because he chooses to sign elsewhere, to me it would depend on the complete terms of the deal and whether the Sox made a strong/reasonable offer. I still don't think he's the kind of player to break the bank for, especially for a team that's far from a serious WS contender. If Boras shopped a 3/75 deal to the Sox, what would a reasonable counter be, given the totality of the circumstances?

And he's not getting 7/210 from anyone.
If Boras came to Boston and said Montgomery is being offered 3/75 but Boston can get him with 3/84 ($3m more per year), I'd totally do that if I'm Boston. You're not breaking the bank by signing him to just three years.
 

HfxBob

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Is it that simple, though? A 3/75 contract from Texas would keep more money in Monty's pocket than the same contract from Boston, and every indicator I see tells me he'd rather be there, even if all things were equal. How much of a premium do you think would be reasonable in that case? What if the hypothetical 3/75 contract has an opt out after year one?

I won't be pissed simply because he chooses to sign elsewhere, to me it would depend on the complete terms of the deal and whether the Sox made a strong/reasonable offer. I still don't think he's the kind of player to break the bank for, especially for a team that's far from a serious WS contender. If Boras shopped a 3/75 deal to the Sox, what would a reasonable counter be, given the totality of the circumstances?

And he's not getting 7/210 from anyone.
I think the 2023 baseball season should have shown us that "far from a serious WS contender" doesn't mean what it used to.

The teams that met in the 2023 World Series won 90 games and 84 games, after winning 68 games and 74 games the season before.

Just about anything can happen the way the system is set up now.
 

Cassvt2023

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If Boras came to Boston and said Montgomery is being offered 3/75 but Boston can get him with 3/84 ($3m more per year), I'd totally do that if I'm Boston. You're not breaking the bank by signing him to just three years.
The hypothetical of a 3/75 is unrealistic. There would definitely include an opt out in that scenario much like Bellinger’s deal. This is Jordan Montgomery’s absolute best chance to cash in. He can bet on himself with a pillow deal and put himself back out there in a year, or he can take whatever the best deal he is getting now that is also a place he wants to be. But a straight 3/75 or 3/84 ain’t happening. Why would he want to do this all over again at 34 yrs old?
 

BigSoxFan

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The hypothetical of a 3/75 is unrealistic. There would definitely include an opt out in that scenario much like Bellinger’s deal. This is Jordan Montgomery’s absolute best chance to cash in. He can bet on himself with a pillow deal and put himself back out there in a year, or he can take whatever the best deal he is getting now that is also a place he wants to be. But a straight 3/75 or 3/84 ain’t happening. Why would he want to do this all over again at 34 yrs old?
Risk management? He’s not young and one major injury can cost him tens of millions. Not sure why he’d expect next year to be any different than this one - he’d be a year older and who knows about how he’ll do in 2024 without a normal ST.

I think 3/75 with an opt-out would be a decent fall back option for him. The dreams of those 6/150 type deals are probably gone for good.
 

RS2004foreever

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Is it that simple, though? A 3/75 contract from Texas would keep more money in Monty's pocket than the same contract from Boston, and every indicator I see tells me he'd rather be there, even if all things were equal. How much of a premium do you think would be reasonable in that case? What if the hypothetical 3/75 contract has an opt out after year one?

I won't be pissed simply because he chooses to sign elsewhere, to me it would depend on the complete terms of the deal and whether the Sox made a strong/reasonable offer. I still don't think he's the kind of player to break the bank for, especially for a team that's far from a serious WS contender. If Boras shopped a 3/75 deal to the Sox, what would a reasonable counter be, given the totality of the circumstances?

And he's not getting 7/210 from anyone.
4 years $100 with a fifth year conditional based on performance and an opt-out after year 2.
I would give him 5/125 in a heartbeat. I doubt he signs for less than 5.
 

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4 years $100 with a fifth year conditional based on performance and an opt-out after year 2.
I would give him 5/125 in a heartbeat. I doubt he signs for less than 5.
My completely unscientific baseline for negotiations has been 4/110 for a while now, and the 4/100 with an opt out after year two and a conditional fifth year option is certainly something I think should absolutely be on the table. A 5/125 straight deal I think I'd be OK with, but that puts Monty at 36 looking for his last cash in, so I'm not sure that would be more attractive to him than having an opt out at 33. Maybe offer the 5/125 with an opt out after years three and four, and a big number club option for year six with a buyout?

I would not be thrilled with a deal that gives him an opt out after this year. I wouldn't necessarily be pissed, either, depending on the other terms, but most of his allure for me is in stabilizing the pitching staff for at least a couple/few years.

Edit: Edited terms due to the maths
 
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After looking at what the Sox did with Giolito, I’m confident that they know how to work the options and opt outs so that they’re getting some value (potentially). I think they’re fine with a shorter term deal plus opt out because it’s essentially buying a draft pick via QO.
 

nvalvo

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If Montgomery wants a long deal because he sees this as his one shot at FA, what about a low-AAV deal with performance escalators?

Say 7 years with $105m ($15 per) guaranteed. But each year of the deal in which he throws 100+ IP he gets a meaningful bonus depending on the final IP figure. Say it's $4m for reaching the 100 IP threshold, with an extra $1m for each 20 IP on top of that. A deal like that gives him the upside of a $150m+ deal if things go really well, but protects the team somewhat in case he doesn't hold up.

I don't actually know how the CBA views a deal like that for CBT purposes.
 

moondog80

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4 years $100 with a fifth year conditional based on performance and an opt-out after year 2.
I would give him 5/125 in a heartbeat. I doubt he signs for less than 5.

I don't know why someone would give him 5 after seeing Chapman and Bellinger settle for 3.

Opening day for most teams is two weeks from Thursday.
 

RS2004foreever

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I don't know why someone would give him 5 after seeing Chapman and Bellinger settle for 3.

Opening day for most teams is two weeks from Thursday.
Because reliable pitching is a scarcer resource than what either Chapman or Bellinger provide.
My completely unscientific baseline for negotiations has been 4/110 for a while now, and the 4/100 with an opt out after year two and a conditional fifth year option is certainly something I think should absolutely be on the table. A 5/125 straight deal I think I'd be OK with, but that puts Monty at 36 looking for his last cash in, so I'm not sure that would be more attractive to him than having an opt out at 33. Maybe offer the 5/125 with an opt out after years three and four, and a big number club option for year six with a buyout?

I would not be thrilled with a deal that gives him an opt out after this year. I wouldn't necessarily be pissed, either, depending on the other terms, but most of his allure for me is in stabilizing the pitching staff for at least a couple/few years.

Edit: Edited terms due to the maths
The press says Montgomery wants 7 years - lets assume he really wants six.
So a deal would have the 6th year option based on performance incentives, and you give him an option after year 2.
5 years plus a 6th options based on starts and WHIP would be fine.

This is EROD's 5th year vesting option on his 4 year $80 million deal. Give that as a 6th year.
  • 2028 Vesting Option includes a $6M buyout
    $17M with 150 IP in 2027 or 300 IP across 2026-27
    $18M with 175 IP in 2027 or 350 IP across 2026-27
 

DennyDoyle'sBoil

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I think the writing is on the wall. The good ship Monty has sailed.

The Red Sox have quietly been shifting dollars from future years into 2024. Right down to spending $17 million in 2024 for years of control for Grissom. I think the idea pretty clearly is to try to use this year’s cap to compete more cheaply in future years, but the time shifting of $9 million of Bello’s future salary to 2024 makes pretty clear what we are looking at here.

I guess maybe they could structure something to stay under for 2023. But it just does not seem to be the model they are going with right now.
 

HfxBob

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Because reliable pitching is a scarcer resource than what either Chapman or Bellinger provide.

The press says Montgomery wants 7 years - lets assume he really wants six.
So a deal would have the 6th year option based on performance incentives, and you give him an option after year 2.
5 years plus a 6th options based on starts and WHIP would be fine.

This is EROD's 5th year vesting option on his 4 year $80 million deal. Give that as a 6th year.
  • 2028 Vesting Option includes a $6M buyout
    $17M with 150 IP in 2027 or 300 IP across 2026-27
    $18M with 175 IP in 2027 or 350 IP across 2026-27
Agreed on all this. As much as I want us to sign him, his credentials do not merit anything beyond a guaranteed 5 years.
 

6-5 Sadler

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After looking at what the Sox did with Giolito, I’m confident that they know how to work the options and opt outs so that they’re getting some value (potentially).
Is the Giolito contract really the best example of this? Many felt that it was a poor structure at the time as it didn’t provide the team with enough value given the downside risk.

That the contract is seemingly going to be pretty disastrous is unfortunate but injury/poor performance was always a realistic outcome.
 

CR67dream

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I don't know why someone would give him 5 after seeing Chapman and Bellinger settle for 3.

Opening day for most teams is two weeks from Thursday.
Those are both pillow contracts with opt outs after this year. They are also position players so I don't know how closely the situations can be comped.

The talk of longer deals is based on Montgomery's reported interest in getting a longer term deal done now so he doesn't have to repeat the process when he's older than he is now and has a QO attached (unless he waits a few more weeks until the season starts to sign somewhere). If he does wait, my guess is he's given up on a long term deal that works for him until next year, and will get an opt out after year one from someone.
 

Sin Duda

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Is the Giolito contract really the best example of this? Many felt that it was a poor structure at the time as it didn’t provide the team with enough value given the downside risk.

That the contract is seemingly going to be pretty disastrous is unfortunate but injury/poor performance was always a realistic outcome.
I don't claim to be an MLB Starting Pitcher contracts expert, and so I trust that Breslow (for now) knows what he's doing regarding these contracts. But that Giolito contract is definitely not a "disaster" yet. First of all, it's 3 years, $58M max. We don't yet know if he needs TJS, but if so, he can still give us 1.5 years. That would probably make it a "bad" contract then, but not a disaster. Sales, Panda ... those were disasters.
 

moondog80

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They are also position players so I don't know how closely the situations can be comped.
Why should we expect it to be different based on that? Don't position players typically get longer deals than pitchers?


The talk of longer deals is based on Montgomery's reported interest in getting a longer term deal done now so he doesn't have to repeat the process when he's older than he is now and has a QO attached (unless he waits a few more weeks until the season starts to sign somewhere). If he does wait, my guess is he's given up on a long term deal that works for him until next year, and will get an opt out after year one from someone.
I get that he wants a longer term deal. Lots of guys do. It doesn't appear to be in the cards.

You may be onto something with waiting until the season starts, though I wonder how much less a team would be willing to pay if it they couldn't start him until what, 4 or 5 turns through the rotation?
 

CR67dream

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I get that he wants a longer term deal. Lots of guys do. It doesn't appear to be in the cards.
Certainly not a 7-year deal, but will he settle for 4, 5 or a possible 6 with some creativity? I just don't know. The market/situations/goals for all of these free agents can differ significantly. All I am expressing is what I think would be some reasonable parameters if such a deal is plausible given what the market appears to be, and Montgomery's own reported wishes.

While I have no confidence in my ability to actually accurately predict what will happen, my preference would be that he's willing to sign a deal here that keeps guarantees to 4 or 5 years in exchange for an opt-out after year two. As I said, I don't think there's a ton of value in an opt-out after one year for the Sox, though I could certainly live with it.
 

nvalvo

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I think the writing is on the wall. The good ship Monty has sailed.

The Red Sox have quietly been shifting dollars from future years into 2024. Right down to spending $17 million in 2024 for years of control for Grissom. I think the idea pretty clearly is to try to use this year’s cap to compete more cheaply in future years, but the time shifting of $9 million of Bello’s future salary to 2024 makes pretty clear what we are looking at here.

I guess maybe they could structure something to stay under for 2023. But it just does not seem to be the model they are going with right now.
This is where the circularity creeps into the argument. You have some very reasonable observations about what the team is up to, but they are based on the premise that we’re not exceeding the cap.

And maybe we’re not! There has been reporting to that effect, and a bunch of incoherent mixed messaging in the team’s public statements. But there’s also a 20-year track record with this ownership group of exceeding the cap about half the time. Maybe Cotillo and friends are right, and something changed between when they were reportedly prepared to offer Yamamoto $300m and January that sharply curtailed the team’s finances. Or maybe not! Maybe this all n-dimensional chess with Boras, and the budget is more or less what it usually is: the CBT, give or take a bit.

In other words, maybe you’re right and the Bello extension happening this week is a sign that they don’t think they can sign Montgomery to a deal they can afford, so their using their budget space to move money into 2024 from future years. Or maybe it was timed to coincide with the DR series for PR reasons, or after the new pitching guys could get a good look at him in ST, or whatever reason. Or maybe it’s a sign that they know (or think they know) what it will take to sign Montgomery more or less, but are waiting for some other shoe to drop: trading Jansen, perhaps, or the disposition of Giolito’s second opinion, or a Snell signing, or whatever. In that scenario, that confidence let them know that they could afford to extend Bello now.

I’m not saying I know anything with any confidence either. We’ll find out, I guess. Maybe.
 

koufax32

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I think the writing is on the wall. The good ship Monty has sailed.

The Red Sox have quietly been shifting dollars from future years into 2024. Right down to spending $17 million in 2024 for years of control for Grissom. I think the idea pretty clearly is to try to use this year’s cap to compete more cheaply in future years, but the time shifting of $9 million of Bello’s future salary to 2024 makes pretty clear what we are looking at here.

I guess maybe they could structure something to stay under for 2023. But it just does not seem to be the model they are going with right now.
At the risk of speaking for others, the “use money now to compete more cheaply in the future” approach does not rule out a Montgomery signing. Nobody here is having illusions of grandeur this season. Johnny from Burger King might, but nobody here that I’m aware of. To me, a JM signing would be more about rotation stability for next year and 2-3 seasons beyond that when their hypothetical window begins to open wider. Why but now then? How often can you get a solid starter like that for somewhat reasonable dollars without forfeiting a draft pick and pool bonus $? That opportunity is now, not 1-2 years from now.

I know you’re not arguing that people shouldn’t be frustrated. Maybe it’s cathartic to air that frustration anyway. Part of being a big money team should be being opportunistic when situations like these present themselves. I’m not impressed with what seems to be too rigid of a plan.
 

ZMart100

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but the time shifting of $9 million of Bello’s future salary to 2024 makes pretty clear what we are looking at here.
The cap hit has moved, but the money really hasn't for Bello. If FSG cares about cash expenditures this year, nothing has changed much there.
 

Cassvt2023

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Because reliable pitching is a scarcer resource than what either Chapman or Bellinger provide.

The press says Montgomery wants 7 years - lets assume he really wants six.
So a deal would have the 6th year option based on performance incentives, and you give him an option after year 2.
5 years plus a 6th options based on starts and WHIP would be fine.

This is EROD's 5th year vesting option on his 4 year $80 million deal. Give that as a 6th year.
  • 2028 Vesting Option includes a $6M buyout
    $17M with 150 IP in 2027 or 300 IP across 2026-27
    $18M with 175 IP in 2027 or 350 IP across 2026-27
I don’t recall ever seeing language in a contract that gives incentive bonuses for WHIP. Can anyone on here find an instance of this?

Also, I’m doubting whether JM has even received 5 years guaranteed from anyone. Can you think of a team this late in the game that may still have this in their budget? ( the NYY seemed to have focused on Snell, on their terms, and they know Montgomery quite well. wonder what that’s about…)
 

DennyDoyle'sBoil

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This is where the circularity creeps into the argument. You have some very reasonable observations about what the team is up to, but they are based on the premise that we’re not exceeding the cap.

And maybe we’re not! There has been reporting to that effect, and a bunch of incoherent mixed messaging in the team’s public statements. But there’s also a 20-year track record with this ownership group of exceeding the cap about half the time. Maybe Cotillo and friends are right, and something changed between when they were reportedly prepared to offer Yamamoto $300m and January that sharply curtailed the team’s finances. Or maybe not! Maybe this all n-dimensional chess with Boras, and the budget is more or less what it usually is: the CBT, give or take a bit.

In other words, maybe you’re right and the Bello extension happening this week is a sign that they don’t think they can sign Montgomery to a deal they can afford, so their using their budget space to move money into 2024 from future years. Or maybe it was timed to coincide with the DR series for PR reasons, or after the new pitching guys could get a good look at him in ST, or whatever reason. Or maybe it’s a sign that they know (or think they know) what it will take to sign Montgomery more or less, but are waiting for some other shoe to drop: trading Jansen, perhaps, or the disposition of Giolito’s second opinion, or a Snell signing, or whatever. In that scenario, that confidence let them know that they could afford to extend Bello now.

I’m not saying I know anything with any confidence either. We’ll find out, I guess. Maybe.
At the risk of speaking for others, the “use money now to compete more cheaply in the future” approach does not rule out a Montgomery signing. Nobody here is having illusions of grandeur this season. Johnny from Burger King might, but nobody here that I’m aware of. To me, a JM signing would be more about rotation stability for next year and 2-3 seasons beyond that when their hypothetical window begins to open wider. Why but now then? How often can you get a solid starter like that for somewhat reasonable dollars without forfeiting a draft pick and pool bonus $? That opportunity is now, not 1-2 years from now.

I know you’re not arguing that people shouldn’t be frustrated. Maybe it’s cathartic to air that frustration anyway. Part of being a big money team should be being opportunistic when situations like these present themselves. I’m not impressed with what seems to be too rigid of a plan.
I am definitely assuming they are treating the tax cutoff as a hard cap and admit I could be wrong. But I’d note that Bello is not the only time shift measure they seem to have undertaken. They took on a $5 million tax hit for Hendriks. They took on $17 million for Sale to get a cost controlled player in future years. They tacked on $8 million for Bello. That is $30 million in 2024 tax hits for tax reduction in future years. That seems like a defeating strategy if you are going to take a +1 on an over the cap year.

If Monty’s price falls low enough that they can lock up additional years of good value pitching, I certainly hope they have the flexibility not to be dogmatic and to pivot in the best interests of the club. But just seeing these other moves makes it hard to imagine that is really on the radar. I think it is more likely they will continue to look for opportunities to get bargains in future years by spending what remains under the cap now.

Of course, if they trade Jansen or something they could do both.
 

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I don’t recall ever seeing language in a contract that gives incentive bonuses for WHIP. Can anyone on here find an instance of this?
I don't think it's allowed. You can have bonuses based on playing time metrics - games, plate appearances, innings pitched, etc. But bonuses on specific performance metrics can't be included in contracts. The closest you can do is to tie bonuses to award finishes.
 

CR67dream

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I don't think it's allowed. You can have bonuses based on playing time metrics - games, plate appearances, innings pitched, etc. But bonuses on specific performance metrics can't be included in contracts. The closest you can do is to tie bonuses to award finishes.
Yes I believe this is correct.
 

nvalvo

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I am definitely assuming they are treating the tax cutoff as a hard cap and admit I could be wrong. But I’d note that Bello is not the only time shift measure they seem to have undertaken. They took on a $5 million tax hit for Hendriks. They took on $17 million for Sale to get a cost controlled player in future years. They tacked on $8 million for Bello. That is $30 million in 2024 tax hits for tax reduction in future years. That seems like a defeating strategy if you are going to take a +1 on an over the cap year.

If Monty’s price falls low enough that they can lock up additional years of good value pitching, I certainly hope they have the flexibility not to be dogmatic and to pivot in the best interests of the club. But just seeing these other moves makes it hard to imagine that is really on the radar. I think it is more likely they will continue to look for opportunities to get bargains in future years by spending what remains under the cap now.

Of course, if they trade Jansen or something they could do both.
I think we pretty much agree. If Montgomery ends available at a good enough value that it’s a no brainer, I imagine they’ll make it work.
 

The Gray Eagle

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It's frustrating that less than 3 weeks from opening day, there are still free agents out there who would likely make this team better but we're probably not going to sign any of them. Not just Snell and Montgomery, but Lorenzen, Duvall, Solano, JD Davis.

The position player ones don't seem like they are going to get anything more than one-year deals at modest money but we don't seem to be even rumored to be interested in any of them.

Looks like we are just going to roll with what we have now.
 

moondog80

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It's frustrating that less than 3 weeks from opening day, there are still free agents out there who would likely make this team better but we're probably not going to sign any of them. Not just Snell and Montgomery, but Lorenzen, Duvall, Solano, JD Davis.
Interesting that the Giants had zero takers for JD Davis at 6.9 mil. Doesn't bode well for the Phams and Duvalls.
 

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Is the Giolito contract really the best example of this? Many felt that it was a poor structure at the time as it didn’t provide the team with enough value given the downside risk.

That the contract is seemingly going to be pretty disastrous is unfortunate but injury/poor performance was always a realistic outcome.
I don’t think Giolitto’s deal is working out well given the injury, but at the very least with the option structure they’re still likely to get him for 1.5 years. Ironically given the concerns we had earlier in the offseason this is now likely to be more within the adjusted competitive window. Story is another example (which may point to it being a FO thing rather than a COBO thing) where if he triggers his opt out, then the Sox can override it, rather than just losing him.

I’m pretty confident that if the Sox do land Monty, we won’t be looking at the deal and thinking it’s terrible.
 

Sandy Leon Trotsky

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Is there a point where Breslow says “deal is X amount on 3/15 and starts to drop after that point”?
Would that even move anything?
 

moondog80

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Is there a point where Breslow says “deal is X amount on 3/15 and starts to drop after that point”?
Would that even move anything?
I think Boras would see right through that. Really, you're not going to offer my guy the same deal you did last week?

The x factor would be if they say "look, if you don't accept this now, we are spending out tax space elsewhere". Maybe you have a Casas extension lined up, and you tell them you're starting it now to use up the tax space, but let it be known you'll adjust that if Monty takes the deal.
 

MFYankees

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Cot's currently estimates us as $30M under the cap and Spotrac estimates us at $48M under (although I don't understand Spotrac's math).
 

simplicio

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Cot's currently estimates us as $30M under the cap and Spotrac estimates us at $48M under (although I don't understand Spotrac's math).
Redsoxpayrolls has us at $214m ($23m under), possibly slightly more if any of their milb deals make it to Boston.
 

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I doubt anyone has offered Montgomery five years guaranteed, and I don’t think the RS should. But I would do four at 22-25 AAV (w/incentives if at the low end) and a fifth year option. That could be the line Breslow has drawn.
 

Cassvt2023

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It’s now March 11. This season starts earlier than most in the past, in less than 10 days. Montgomery hasn’t received anything close to what he was seeking or he would’ve signed by now. E-Rod’s 4/80m was a much better template to go on rather than Rodon’s or Nola’s deals… Boras fucked up and totally misread the market and now he’s scrambling to save face. He’s likely looking for the best pillow deal similar to what Bellinger got and not even finding that. You reap what you sow Scotty B.
 

Cassvt2023

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I doubt anyone has offered Montgomery five years guaranteed, and I don’t think the RS should. But I would do four at 22-25 AAV (w/incentives if at the low end) and a fifth year option. That could be the line Breslow has drawn.
Its likely not up to Breslow. John Henry is adverse to long term deals for starting pitchers that are around 30 years old. He feels he was burned with Price contract and Sale extension from DD. i was really hoping for Imanaga, who has pitched very well in ST and signed for much less than what was projected. Either Breslow wasn’t sold on him or his hands were tied by ownership to give him more than 2-3 years, which would really suck if that were the case.
 

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Redsoxpayrolls has us at $214m ($23m under), possibly slightly more if any of their milb deals make it to Boston.
If that's accurate, then there's no room to stay under and add Montgomery now. Maybe we're back to Jansen has to get moved for there to be any chance?
 

nvalvo

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That's if the CBT threshold is in fact the budget (and under which scenarios), which we've gotten mixed messages about at best.
 

SouthernBoSox

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That's if the CBT threshold is in fact the budget (and under which scenarios), which we've gotten mixed messages about at best.
As Alex Speier mentioned in this last piece. The Bello contract extension structure strongly suggest they won't be adding a big ticket FA this off season. They decided to absorb the higher AAV this year in exchange for keeping it lower in subsequent years.

I think they will add an arm, but it's not going to be Montgomery.

View: https://twitter.com/alexspeier/status/1766988676528001166?s=46

That said, Bello’s deal offers some connecting dots to understanding that the Sox aren’t counting on an addition of Montgomery. In several instances, when the Sox have signed players who were already under team control to long-term deals, they’ve had the extension take effect not in the season when it was signed, but instead for the following one. That approach allowed the club to have the flexibility to stay below the luxury tax threshold or minimize the extent to which it went over the line in the year of the extension’s signing.
 

sezwho

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That's if the CBT threshold is in fact the budget (and under which scenarios), which we've gotten mixed messages about at best.
Any discussions with Casas must imply at least another 10-15 (ish right?) so the budget has to have room for that too.

That might mean a Jansen out before an add, or the budget has more conditionality than first appears like it had 25+ for YY too.

I remain confused.
 

Rovin Romine

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Is the Giolito contract really the best example of this? Many felt that it was a poor structure at the time as it didn’t provide the team with enough value given the downside risk.

That the contract is seemingly going to be pretty disastrous is unfortunate but injury/poor performance was always a realistic outcome.
There's going to be a 20/20 hindsight shift on the way people say they valued the Giolito trade. The downside risk was not catastrophic injury (which is the downside risk of nearly all FA deals). The downside risk was Giolito being mediocre when they thought he was fixable. . .

If you think about it though, the contract heavily incentives Giolito to commit and perform no matter what. He's made $20M in his career, but he's obviously aware he can really cash in as a FA at age 29/30. (There's also the issue of his divorce, which is too personal to go into, but he might now have fewer career earnings and/or benefit from a short-term deal.)

Anyway, the breakdown would be:

2024 (his age 29 season)
-If he excelled in 2024:​
Giolito gets $19M, and hits FA in 2025.​
The Sox get a good year at what would be a fair price/tax hit. Maybe he resigns/extends, and maybe he does not.​
If he pitches well and will opt-out, they can always flip him to a contender if they're otherwise floundering - they'd essentially be trading an impending FA.​
-If he was Meh in 2024 or injured:​
Giolito gets $18M. He could opt into staying with the Sox and working things out - at the risk of a 2026 option if he wasn't a full time starter for any reason. Or he could roll the dice as a FA and pick up $1M. To trigger this option, he'd probably have to be pretty Meh, so much so that he'd prefer to hit FA in 2026/27 instead of now.​
The Sox get either a Meh year for $19M and never see him again, or
The Sox get a Meh (or Meh Minus) year for $18M, and control him in 2025 because he was Meh Minus.​

2025 (his age 30 season) At this point we have to assume that Giolito, for whatever reason, used his player option:
-If he excels in 2025:​
Giolito gets $18M, and if he pitches more than 140 innings, he has a mutual option. AFAIK, that means he's essentially a FA with a $1M(?) buyout.​
The Sox get one meh/bad year and one full year of SP for: $18M, then $18M, and never see him again.​
They can also flip him mid-season if the team is stalling.​
-If he is Meh in 2025 or injured:​
Giolito gets $36M for two Meh/Injured seasons.​
The Sox get the same, and also an option for $14M for 2026 if he pitches less than 140 innings. (25 ish starts.)​
They'd only really exercise the option if they thought he'd be worth it in 2026, which sounds obvious, but for two points. 1) $14M might be the going rate for an averageish starter by that point. 2) He'd have logged two substandard seasons in a row. . .so the most common scenario for this is what we're seeing now. Injury in 2024 triggers the 2025 player option, and he's not a full fledged starter in 2026. But maybe he comes back at the ASB and finishes strong.​
Ultimately, that's: $18M for nothing in 2024, $18M for a partial in 2025, and $14M in 2026. Or the Sox can just cut bait after 2025 if they don't think he's a good bounce-back candidate in 2026. In any event they don't have a​

2026 (his age 31 season):
There's no future trigger for control here, but if Giolito is pitching in this circumstance, he's been injured or ineffective, but there's some upside for the club (otherwise they'd have let him go.) He still has an incentive to do well and hit FA in 2027 for his age 32 season. He'll have earned a total of $50M or so over 3 years. Which is not nothing, but he's likely to earn more/get a longer deal if he hits the FA market or negotiates an extension when he's 30 as opposed to 32.​
 

Sausage in Section 17

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Montgomery's $25m salary then won't really be an "albatross".
This is where we will have to disagree. The list of highest contracts ever given out to pitchers is littered with albatrosses. There are probably more horrible contracts on this list than players who lived up to them. And of the top 3 on the list, none will be able to start the season. Only 2 out of the top 8 were available for the playoffs last year. And I'm not sure Jordan Montgomery has ever had a season on par with the best of these other players. Just because he may be among the top 30 pitchers currently doesn't mean he is going to be worth ace money. Very few of the the top 30 pitchers ever really are.

Starting pitchers
The highest-paid starting pitchers, by average annual value:
1. Shohei Ohtani, $46,081,476 (2024-33) (reduced for deferrals)
2. Max Scherzer, $43,333,333 (2022-24)
… Justin Verlander, $43,333,333 (2023-24)
4. Zack Wheeler, $42,000,000 (2025-27)
5. Jacob deGrom, $37,000,000 (2023-27)
6. Gerrit Cole, $36,000,000 (2020-28)
7. Stephen Strasburg, $35,000,000 (2020-26)
8. Trevor Bauer, $34,000,000 (2021-23)
9. Justin Verlander, $33,000,000 (2020-21)
10. Zack Greinke, $32,500,000 (2016-21) (reduced for deferrals)
11. David Price, $31,000,000 (2016-22)
… Clayton Kershaw, $31,000,000 (2019-21)
13. Clayton Kershaw, $30,714,286 (2014-20)
14. Max Scherzer, $30,000,000 (2015-21)
15. Shohei Ohtani, $30,000,000 (2023)
16. Jacob deGrom, $27,500,000 (2019-23)
17. Tyler Glasnow, $27,312,500 (2024-28)
18. Yoshinobu Yamamoto, $27,083,333 (2024-35)
19. Carlos Rodón, $27,000,000 (2023-28)
20. Jon Lester, $25,833,333 (2015-20)
21. Justin Verlander, $25,714,286 (2013-19)
22. Chris Sale, $25,600,000 (2020-24)
23. Felix Hernandez, $25,000,000 (2013-19)
… Stephen Strasburg, $25,000,000 (2017-23)
… Jake Arrieta, $25,000,000 (2018-20)
… Justin Verlander, $25,000,000 (2022-23)
… Sonny Gray, $25,000,000 (2024-26)
28. Aaron Nola, $24,571,429 (2024-30)
29. Zack Greinke, $24,500,000 (2013-18)
30. CC Sabathia, $24,400,000 (2012-16)
 

6-5 Sadler

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There's going to be a 20/20 hindsight shift on the way people say they valued the Giolito trade. The downside risk was not catastrophic injury (which is the downside risk of nearly all FA deals). The downside risk was Giolito being mediocre when they thought he was fixable. . .
It’s not hindsight though. Below is what I wrote at the time and others shared similar sentiments.

My concern is more with the deal structure. I guess philosophically I’m against giving pitchers 2 year deals with opt outs after one year unless there is a huge discount in year one. There is such an asymmetry in upside vs downside that it’s hard to justify it. If he blows out his elbow or is as ineffective as he was in the 2nd half, you’re out $40M. If he’s awesome and gives you 4 wins, you have surplus value of like $20M and he’s gone after one season.
And of course the downside risk was always catastrophic injury. I would also characterize any sub-meh performance as downside risk but I think we quickly get into a semantics exercise. For instance, Fangraphs had Giolito’s 20th percentile projection at 1.1 WAR which I would classify as sub-meh given his contract but others could differ on that opinion.
 
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