Extensions?

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mattmitchl44
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Re: Extensions?

Post by mattmitchl44 »

FWIW - I would note that when I say maybe 4-5 yrs. at $6 million AAV for Herrera, Burleson, etc. and get two opposing responses:

1) the team shouldn't take that risk!

and

2) that's too low the players would never take that!

That suggests to me that the offer is right in the sweet spot where maybe the risk/reward could work for both the team and the player - both sides get something and give up something.
ecleme22
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Re: Extensions?

Post by ecleme22 »

mattmitchl44 wrote: 02 Dec 2025 03:51 am
ecleme22 wrote: 01 Dec 2025 20:04 pm Sounds super easy until they turn into Piscotty or DeJong.

So why do it?

No reason to unless you're obsessed with maybe saving a little money.

You go ahead and believe in Burleson for another 4-5 years.
Yes, the whole point is for the team to save $5-$10 million a year on a 2+ fWAR player vs. what it would otherwise cost them if they had to go buy that guy on the FA market. It's OK to do that. If you then develop another prospect in a couple of years that could take his place, you have trade value (either the prospect or Burleson) that you can potentially use as part of a package trade for players who can fill holes on your roster rather than having to buy them as expensive FAs.

And, as I've already said, you have to do your homework and trust your evaluation of a player like Burleson. If you believe, based on what you know about how you've seen him develop that he'll likely be a 2+ fWAR player going forward and a consistent part of your starting lineup, you lean toward extending him. If you think his 2+ fWAR season in 2025 at age 26 as he enters his prime was a fluke and he's unlikely to repeat that level of production going forward, I'd lean toward trying to "trade high" on him right now.
Funny how really the only homegrown Cards position player who has had real sustained, uninterupted success in the last 10 YEARS is Donovan. Every other, player has regressed or been injured. (Winn is only two years in so I don't count him just yet).

So just looking at the clarity of hindsight, the only position player since 2014ish that may have been successfully extended is Donovan.


And as it stands... Donovan has two years left, is due to make a low 5.4mil in arbitration in 2026, and will be a FA at 30 years old.

Donovan's salaries:
2023: 728K
2024: 757K
2025: 2.850mil
2026: 5.4 mil (projected)

But if it were you, you would've said after, say, the 2022 season, "let's lock him up" and given him 7 year/42mil deal, which would keep him here for 2 more years after FA.

Now let's say in arbitration in 2027 he gets 10mil and the Cards keep him! We would've had him for 5 years, spent a total of just under 20mil, and are parting with him at 30 years old.

So why extend him? We have JJ about ready to take his place, are getting prospects for him and he cost us less than 5mil during his ENTIRE Cards tenure if he's traded now...
renostl
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Re: Extensions?

Post by renostl »

ecleme22 wrote: 02 Dec 2025 11:21 am
mattmitchl44 wrote: 02 Dec 2025 03:51 am
ecleme22 wrote: 01 Dec 2025 20:04 pm Sounds super easy until they turn into Piscotty or DeJong.

So why do it?

No reason to unless you're obsessed with maybe saving a little money.

You go ahead and believe in Burleson for another 4-5 years.
Yes, the whole point is for the team to save $5-$10 million a year on a 2+ fWAR player vs. what it would otherwise cost them if they had to go buy that guy on the FA market. It's OK to do that. If you then develop another prospect in a couple of years that could take his place, you have trade value (either the prospect or Burleson) that you can potentially use as part of a package trade for players who can fill holes on your roster rather than having to buy them as expensive FAs.

And, as I've already said, you have to do your homework and trust your evaluation of a player like Burleson. If you believe, based on what you know about how you've seen him develop that he'll likely be a 2+ fWAR player going forward and a consistent part of your starting lineup, you lean toward extending him. If you think his 2+ fWAR season in 2025 at age 26 as he enters his prime was a fluke and he's unlikely to repeat that level of production going forward, I'd lean toward trying to "trade high" on him right now.
Funny how really the only homegrown Cards position player who has had real sustained, uninterupted success in the last 10 YEARS is Donovan. Every other, player has regressed or been injured. (Winn is only two years in so I don't count him just yet).

So just looking at the clarity of hindsight, the only position player since 2014ish that may have been successfully extended is Donovan.


And as it stands... Donovan has two years left, is due to make a low 5.4mil in arbitration in 2026, and will be a FA at 30 years old.

Donovan's salaries:
2023: 728K
2024: 757K
2025: 2.850mil
2026: 5.4 mil (projected)

But if it were you, you would've said after, say, the 2022 season, "let's lock him up" and given him 7 year/42mil deal, which would keep him here for 2 more years after FA.

Now let's say in arbitration in 2027 he gets 10mil and the Cards keep him! We would've had him for 5 years, spent a total of just under 20mil, and are parting with him at 30 years old.

So why extend him? We have JJ about ready to take his place, are getting prospects for him and he cost us less than 5mil during his ENTIRE Cards tenure if he's traded now...
Sorry to butt in,

I think that Donnie is the kind of player you can do this with for a multitude of reasons.
For one, in the above example, you would have the player for 2 more seasons. His 30 and 31 seasons
at that. Those are usually good, and his replacement will not play for free and could be less productive.
A weaker team. Both he and JJ easily coexist. Players like BD or shorts stops aren't locked to one position
a fact that is increasing his TV today.

You extend players when you see them as part of a good team. Donovan may have a neutral value once
he starts making that $10+M in the example, but he may also still be a productive part of decent teams
even if he is hitting in the #7 or #8 spot in the lineup. Which would make him still a player of value
if a trade is indeed needed/wanted. Peak value absolutely not, but the team got peak play on the
field where it really counts. That's why we watch the team play.

Nice discussion with slightly different opinions is great. I kind of think extensions on what many
of us see as players that should be able to be replaced from within the organization makes some
sense. They still fall into normal productive seasons. The costs are such that any team
that wants them won't blink. They are players that wouldn't be QO, so even with a decreased
return in a trade it is better than zero. I am also biased to those mid-level vets. IF teams don't
have them they're looking for them even the $300M teams.

All said, I do think extensions should be very few.
rockondlouie
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Re: Extensions?

Post by rockondlouie »

IF the whole point of these early extensions matt keeps pushing for is to "save $5M-$10M", then let's put a STOP to that thinking right now!

These are the ST. LOUIS CARDINALS, a franchise worth over $2.5B that BDWJr & partners were GIFTED by A-B for $150M minus the $75+M they immediately reaped selling off the garages and some land!

The ST . LOUIS CARDINALS do NOT have to squeeze out "$5M-$10M" in savings like they're the Pirates, A's or Rockies!

Dewitt has made hundreds of millions of dollars in profits, reaping the rewards from a fan base that had given him TWENTY-THREE (23) years of 3+M in attendance, competed in 67 playoff games and four World Series winning two!

Dewitt doesn't have to pinch pennies w/risky extensions that may or may not be warranted.

He can easily afford any player in MLB sans the very, very top (re: Ohtani/Soto types) of the payroll pay scale!

He simply refuses to do so.............BY CHOICE, NOT BY lack of means.

JMO
mattmitchl44
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Re: Extensions?

Post by mattmitchl44 »

ecleme22 wrote: 02 Dec 2025 11:21 am
mattmitchl44 wrote: 02 Dec 2025 03:51 am
ecleme22 wrote: 01 Dec 2025 20:04 pm Sounds super easy until they turn into Piscotty or DeJong.

So why do it?

No reason to unless you're obsessed with maybe saving a little money.

You go ahead and believe in Burleson for another 4-5 years.
Yes, the whole point is for the team to save $5-$10 million a year on a 2+ fWAR player vs. what it would otherwise cost them if they had to go buy that guy on the FA market. It's OK to do that. If you then develop another prospect in a couple of years that could take his place, you have trade value (either the prospect or Burleson) that you can potentially use as part of a package trade for players who can fill holes on your roster rather than having to buy them as expensive FAs.

And, as I've already said, you have to do your homework and trust your evaluation of a player like Burleson. If you believe, based on what you know about how you've seen him develop that he'll likely be a 2+ fWAR player going forward and a consistent part of your starting lineup, you lean toward extending him. If you think his 2+ fWAR season in 2025 at age 26 as he enters his prime was a fluke and he's unlikely to repeat that level of production going forward, I'd lean toward trying to "trade high" on him right now.
Funny how really the only homegrown Cards position player who has had real sustained, uninterupted success in the last 10 YEARS is Donovan. Every other, player has regressed or been injured. (Winn is only two years in so I don't count him just yet).

So just looking at the clarity of hindsight, the only position player since 2014ish that may have been successfully extended is Donovan.


And as it stands... Donovan has two years left, is due to make a low 5.4mil in arbitration in 2026, and will be a FA at 30 years old.

Donovan's salaries:
2023: 728K
2024: 757K
2025: 2.850mil
2026: 5.4 mil (projected)

But if it were you, you would've said after, say, the 2022 season, "let's lock him up" and given him 7 year/42mil deal, which would keep him here for 2 more years after FA.

Now let's say in arbitration in 2027 he gets 10mil and the Cards keep him! We would've had him for 5 years, spent a total of just under 20mil, and are parting with him at 30 years old.

So why extend him? We have JJ about ready to take his place, are getting prospects for him and he cost us less than 5mil during his ENTIRE Cards tenure if he's traded now...
To be clear, my idea is you want to have your "core" players signed through age 30, with 1 or 2 team options years for age 31 and age 32.

So, for Donovan after the 2022 season, that would have been a 5 year contract plus two team option years. But then that's covering two pre-ARB years and three ARB years, plus two team options for his first two FA years. If you go through ARB that would be about $1M, $1M, $3M, $6M, $10M ($21M), so if you are guaranteeing up front, it has to total to less than that.

The guaranteed part of that is going to be like 5 yrs./$17 million ($1M, $1M, $3M, $5M, $7M) plus a team option for $12 million in 2028 and for $15 million in 2029.

If you had Donovan locked in for $5M in 2026, $7M in 2027, and two team options for $12 million in 2028 and for $15 million in 2029, he'd be and even more valuable trade commodity than he is right now.
mattmitchl44
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Re: Extensions?

Post by mattmitchl44 »

rockondlouie wrote: 02 Dec 2025 13:32 pm IF the whole point of these early extensions matt keeps pushing for is to "save $5M-$10M", then let's put a STOP to that thinking right now!
If the Cardinals can "save" $5M a year on three young players because they signed them early to team friendly contracts, that's $15 million in payroll for the year that is freed up - half of what they would need to go sign a #1/#2 SP. You don't think that is significant?
rockondlouie
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Re: Extensions?

Post by rockondlouie »

mattmitchl44 wrote: 02 Dec 2025 13:58 pm
rockondlouie wrote: 02 Dec 2025 13:32 pm IF the whole point of these early extensions matt keeps pushing for is to "save $5M-$10M", then let's put a STOP to that thinking right now!
If the Cardinals can "save" $5M a year on three young players because they signed them early to team friendly contracts, that's $15 million in payroll for the year that is freed up - half of what they would need to go sign a #1/#2 SP. You don't think that is significant?
H E L L NO I don't think that's significant when put into context.

Re-read my post matt.

BDWJr isn't some charity case like you're making him out to be who needs to "save" $5M on three young players. :roll:

He can easily afford to sign any player in MLB sans the type I mentioned (Ohtani/Soto types).

IF (and it's a BIG "IF") one of these players (Winn, Bumbles, Hererra, etal) does become an all-star caliber player over the next two-three seasons, then BDWJr can easily afford to retain them since they'll never be in that Ohtani/Soto price range.

Again

You're treating Dewitt and The Cardinals like they're some charity case when they certainly are not.

Stop falling for Dewitt's payroll slashing scam and pleas of "poor mouth" when the man and his partners have reaped multi-hundreds of millions in profits and garnered billions of dollars in capital gains on their investment.
renostl
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Re: Extensions?

Post by renostl »

mattmitchl44 wrote: 02 Dec 2025 13:56 pm
ecleme22 wrote: 02 Dec 2025 11:21 am
mattmitchl44 wrote: 02 Dec 2025 03:51 am
ecleme22 wrote: 01 Dec 2025 20:04 pm Sounds super easy until they turn into Piscotty or DeJong.

So why do it?

No reason to unless you're obsessed with maybe saving a little money.

You go ahead and believe in Burleson for another 4-5 years.
Yes, the whole point is for the team to save $5-$10 million a year on a 2+ fWAR player vs. what it would otherwise cost them if they had to go buy that guy on the FA market. It's OK to do that. If you then develop another prospect in a couple of years that could take his place, you have trade value (either the prospect or Burleson) that you can potentially use as part of a package trade for players who can fill holes on your roster rather than having to buy them as expensive FAs.

And, as I've already said, you have to do your homework and trust your evaluation of a player like Burleson. If you believe, based on what you know about how you've seen him develop that he'll likely be a 2+ fWAR player going forward and a consistent part of your starting lineup, you lean toward extending him. If you think his 2+ fWAR season in 2025 at age 26 as he enters his prime was a fluke and he's unlikely to repeat that level of production going forward, I'd lean toward trying to "trade high" on him right now.
Funny how really the only homegrown Cards position player who has had real sustained, uninterupted success in the last 10 YEARS is Donovan. Every other, player has regressed or been injured. (Winn is only two years in so I don't count him just yet).

So just looking at the clarity of hindsight, the only position player since 2014ish that may have been successfully extended is Donovan.


And as it stands... Donovan has two years left, is due to make a low 5.4mil in arbitration in 2026, and will be a FA at 30 years old.

Donovan's salaries:
2023: 728K
2024: 757K
2025: 2.850mil
2026: 5.4 mil (projected)

But if it were you, you would've said after, say, the 2022 season, "let's lock him up" and given him 7 year/42mil deal, which would keep him here for 2 more years after FA.

Now let's say in arbitration in 2027 he gets 10mil and the Cards keep him! We would've had him for 5 years, spent a total of just under 20mil, and are parting with him at 30 years old.

So why extend him? We have JJ about ready to take his place, are getting prospects for him and he cost us less than 5mil during his ENTIRE Cards tenure if he's traded now...
To be clear, my idea is you want to have your "core" players signed through age 30, with 1 or 2 team options years for age 31 and age 32.

So, for Donovan after the 2022 season, that would have been a 5 year contract plus two team option years. But then that's covering two pre-ARB years and three ARB years, plus two team options for his first two FA years. If you go through ARB that would be about $1M, $1M, $3M, $6M, $10M ($21M), so if you are guaranteeing up front, it has to total to less than that.

The guaranteed part of that is going to be like 5 yrs./$17 million ($1M, $1M, $3M, $5M, $7M) plus a team option for $12 million in 2028 and for $15 million in 2029.

If you had Donovan locked in for $5M in 2026, $7M in 2027, and two team options for $12 million in 2028 and for $15 million in 2029, he'd be and even more valuable trade commodity than he is right now.
IMO Matt, the "whole point" of extensions is not about saving a million or $10M.
Although ultimately it might versus looking for what was traded away or allowed
to walk away.

It's about identifying players that can be a part of a good to great team and
extending the teams control with them.
There are many pages about trading for players with control. IF we have one in hand
that projects as an important piece why not extend that control?

Mid market teams can afford these guys. IF ID'd correctly, not extending too far in age
34 might be tops, then that player or the players behind him are still marketable. When
traded they are not going to thrifty teams anyway, they will go to teams seeing them
as a part of their own improved team. One player in this range doesn't kill a payroll.

We've seen extensions on star players. IMO those are the ones teams get stuck
with and get stuck quickly on. In fact most end bad, due too the amount of term
and the AAV attached to them. It can be a little counter intuitive. Far better to have
a player live up to a $12M-$15M contract than a $25M-$30M contract.
ecleme22
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Re: Extensions?

Post by ecleme22 »

mattmitchl44 wrote: 02 Dec 2025 13:56 pm
ecleme22 wrote: 02 Dec 2025 11:21 am
mattmitchl44 wrote: 02 Dec 2025 03:51 am
ecleme22 wrote: 01 Dec 2025 20:04 pm Sounds super easy until they turn into Piscotty or DeJong.

So why do it?

No reason to unless you're obsessed with maybe saving a little money.

You go ahead and believe in Burleson for another 4-5 years.
Yes, the whole point is for the team to save $5-$10 million a year on a 2+ fWAR player vs. what it would otherwise cost them if they had to go buy that guy on the FA market. It's OK to do that. If you then develop another prospect in a couple of years that could take his place, you have trade value (either the prospect or Burleson) that you can potentially use as part of a package trade for players who can fill holes on your roster rather than having to buy them as expensive FAs.

And, as I've already said, you have to do your homework and trust your evaluation of a player like Burleson. If you believe, based on what you know about how you've seen him develop that he'll likely be a 2+ fWAR player going forward and a consistent part of your starting lineup, you lean toward extending him. If you think his 2+ fWAR season in 2025 at age 26 as he enters his prime was a fluke and he's unlikely to repeat that level of production going forward, I'd lean toward trying to "trade high" on him right now.
Funny how really the only homegrown Cards position player who has had real sustained, uninterupted success in the last 10 YEARS is Donovan. Every other, player has regressed or been injured. (Winn is only two years in so I don't count him just yet).

So just looking at the clarity of hindsight, the only position player since 2014ish that may have been successfully extended is Donovan.


And as it stands... Donovan has two years left, is due to make a low 5.4mil in arbitration in 2026, and will be a FA at 30 years old.

Donovan's salaries:
2023: 728K
2024: 757K
2025: 2.850mil
2026: 5.4 mil (projected)

But if it were you, you would've said after, say, the 2022 season, "let's lock him up" and given him 7 year/42mil deal, which would keep him here for 2 more years after FA.

Now let's say in arbitration in 2027 he gets 10mil and the Cards keep him! We would've had him for 5 years, spent a total of just under 20mil, and are parting with him at 30 years old.

So why extend him? We have JJ about ready to take his place, are getting prospects for him and he cost us less than 5mil during his ENTIRE Cards tenure if he's traded now...
To be clear, my idea is you want to have your "core" players signed through age 30, with 1 or 2 team options years for age 31 and age 32.

So, for Donovan after the 2022 season, that would have been a 5 year contract plus two team option years. But then that's covering two pre-ARB years and three ARB years, plus two team options for his first two FA years. If you go through ARB that would be about $1M, $1M, $3M, $6M, $10M ($21M), so if you are guaranteeing up front, it has to total to less than that.

The guaranteed part of that is going to be like 5 yrs./$17 million ($1M, $1M, $3M, $5M, $7M) plus a team option for $12 million in 2028 and for $15 million in 2029.

If you had Donovan locked in for $5M in 2026, $7M in 2027, and two team options for $12 million in 2028 and for $15 million in 2029, he'd be and even more valuable trade commodity than he is right now.
Your math is a little off.

You said if BD is signed after the 2022 season, it's: $1M, $1M, $3M, $6M, $10M ($21M)
Then you said: 5 yrs./$17 million ($1M, $1M, $3M, $5M, $7M) plus a team option for $12 million in 2028 and for $15 million in 2029.

I think you mean: $1M, $1M, $3M, $6M, $10M ($21M) Guaranteed. Then, plus a team option for $12 million in 2028 and for $15 million in 2029.

Let's assume you mean that. And the option buyout is 1million. That's 22 mil guaranteed, right, until 2028. And my math was, if he made 10mil in arbitration in 2027, would be about 19mil.

Okay, so with hindsight, it might not be that bad for Donovan.

What if we owed Nootbar a guaranteed 10 mil in 2027? What if, after 2015 and an .855 OPS from a centerfielder, we owed Grichuk 21 million more from 2016-2020?

Maybe we are hoping for the same thing——the org being better about evaluating talent. Perhaps, as I've mentioned about others, my logic is scarred by the way Mo evaluated talent.

So I will say this: I think your point to extend is valid if the org is an educated one. Thank you for the debate.
mattmitchl44
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Re: Extensions?

Post by mattmitchl44 »

ecleme22 wrote: 02 Dec 2025 23:01 pm
mattmitchl44 wrote: 02 Dec 2025 13:56 pm
ecleme22 wrote: 02 Dec 2025 11:21 am
mattmitchl44 wrote: 02 Dec 2025 03:51 am
ecleme22 wrote: 01 Dec 2025 20:04 pm Sounds super easy until they turn into Piscotty or DeJong.

So why do it?

No reason to unless you're obsessed with maybe saving a little money.

You go ahead and believe in Burleson for another 4-5 years.
Yes, the whole point is for the team to save $5-$10 million a year on a 2+ fWAR player vs. what it would otherwise cost them if they had to go buy that guy on the FA market. It's OK to do that. If you then develop another prospect in a couple of years that could take his place, you have trade value (either the prospect or Burleson) that you can potentially use as part of a package trade for players who can fill holes on your roster rather than having to buy them as expensive FAs.

And, as I've already said, you have to do your homework and trust your evaluation of a player like Burleson. If you believe, based on what you know about how you've seen him develop that he'll likely be a 2+ fWAR player going forward and a consistent part of your starting lineup, you lean toward extending him. If you think his 2+ fWAR season in 2025 at age 26 as he enters his prime was a fluke and he's unlikely to repeat that level of production going forward, I'd lean toward trying to "trade high" on him right now.
Funny how really the only homegrown Cards position player who has had real sustained, uninterupted success in the last 10 YEARS is Donovan. Every other, player has regressed or been injured. (Winn is only two years in so I don't count him just yet).

So just looking at the clarity of hindsight, the only position player since 2014ish that may have been successfully extended is Donovan.


And as it stands... Donovan has two years left, is due to make a low 5.4mil in arbitration in 2026, and will be a FA at 30 years old.

Donovan's salaries:
2023: 728K
2024: 757K
2025: 2.850mil
2026: 5.4 mil (projected)

But if it were you, you would've said after, say, the 2022 season, "let's lock him up" and given him 7 year/42mil deal, which would keep him here for 2 more years after FA.

Now let's say in arbitration in 2027 he gets 10mil and the Cards keep him! We would've had him for 5 years, spent a total of just under 20mil, and are parting with him at 30 years old.

So why extend him? We have JJ about ready to take his place, are getting prospects for him and he cost us less than 5mil during his ENTIRE Cards tenure if he's traded now...
To be clear, my idea is you want to have your "core" players signed through age 30, with 1 or 2 team options years for age 31 and age 32.

So, for Donovan after the 2022 season, that would have been a 5 year contract plus two team option years. But then that's covering two pre-ARB years and three ARB years, plus two team options for his first two FA years. If you go through ARB that would be about $1M, $1M, $3M, $6M, $10M ($21M), so if you are guaranteeing up front, it has to total to less than that.

The guaranteed part of that is going to be like 5 yrs./$17 million ($1M, $1M, $3M, $5M, $7M) plus a team option for $12 million in 2028 and for $15 million in 2029.

If you had Donovan locked in for $5M in 2026, $7M in 2027, and two team options for $12 million in 2028 and for $15 million in 2029, he'd be and even more valuable trade commodity than he is right now.
Your math is a little off.

You said if BD is signed after the 2022 season, it's: $1M, $1M, $3M, $6M, $10M ($21M)
Then you said: 5 yrs./$17 million ($1M, $1M, $3M, $5M, $7M) plus a team option for $12 million in 2028 and for $15 million in 2029.

I think you mean: $1M, $1M, $3M, $6M, $10M ($21M) Guaranteed. Then, plus a team option for $12 million in 2028 and for $15 million in 2029.
No, what I tried to say was, if after the 2022 season your best guess of what he'd get if you just go year-to-year in ARB is $1M, $1M, $3M, $6M, $10M ($21M), then what the team is going to offer up front as a five year guarantee is going to be less than that: 5 yrs./$17 million ($1M, $1M, $3M, $5M, $7M).

When the team is going to mitigate all of the player's injury risk, etc. by guaranteeing them their first five years of salary, in advance, the price the team pays should be at least somewhat less than the best guess of that the player would get by going to ARB if they remain healthy and productive. The team is taking on extra long term "risk" and so should get the contract done for somewhat less money.
Let's assume you mean that. And the option buyout is 1million. That's 22 mil guaranteed, right, until 2028. And my math was, if he made 10mil in arbitration in 2027, would be about 19mil.

Okay, so with hindsight, it might not be that bad for Donovan.

What if we owed Nootbar a guaranteed 10 mil in 2027? What if, after 2015 and an .855 OPS from a centerfielder, we owed Grichuk 21 million more from 2016-2020?

Maybe we are hoping for the same thing——the org being better about evaluating talent. Perhaps, as I've mentioned about others, my logic is scarred by the way Mo evaluated talent.

So I will say this: I think your point to extend is valid if the org is an educated one. Thank you for the debate.
You are welcome.

Yes, the organization has to make the right decisions. Again, my whole stance on this is predicated on the organization having to make the evaluation up front that Player X is going to be part of their "core" - a SP in the rotation, a starting position player/DH, of the closer - before they decide to offer an early long term extension. But if they trust their evaluation, whether they think that "core" player is a 2+ fWAR solid regular or a 5+ fWAR All-Star, I think there is value for the team in getting them signed long term at the right price point.

Recognizing that EVERY contract is a "risk/reward" gamble for the team, if I were the team, I would prefer to place my bets on young players still in their primes who I think I've evaluated correctly rather than placing bets on typically much more expensive FAs.
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