Extensions?

[mattmitchl44]

Regarding the "wait for them to earn it" philosophy, as much as CT liked to hate on the Cardinals having extended DeJong for 6 yrs./$26 million after his rookie year, consider what it would have been if they had waited until after the 2019 season when he hit 30 HRs, went to the ASG, and was a top defensive SS.

They could have been talking extending him for 6 years at that point for $100 million or so.

So a tiny early extension paid off in avoiding what would have turned out to be a much bigger mistake later.

[sikeston bulldog2]

Regarding the "wait for them to earn it" philosophy, as much as CT liked to hate on the Cardinals having extended DeJong for 6 yrs./$26 million after his rookie year, consider what it would have been if they had waited until after the 2019 season when he hit 30 HRs, went to the ASG, and was a top defensive SS.

They could have been talking extending him for 6 years at that point for $100 million or so.

So a tiny early extension paid off in avoiding what would have turned out to be a much bigger mistake later.

Players are judged it seems, from year to year. Often it’s hard to replicate a good year. Like a pennant winning team, for personal records the same truth holds- you must have luck, no injuries, and record years.

The following year- team not as good as they don’t have the same luck, don’t get same breaks, etc. well, same for the individual.


My point- you can extend but expect up and down years doing the contract. It’s simple nature.

Therefore, it’s a hit and miss at best.

[C-Unit]

Regarding the "wait for them to earn it" philosophy, as much as CT liked to hate on the Cardinals having extended DeJong for 6 yrs./$26 million after his rookie year, consider what it would have been if they had waited until after the 2019 season when he hit 30 HRs, went to the ASG, and was a top defensive SS.

They could have been talking extending him for 6 years at that point for $100 million or so.

So a tiny early extension paid off in avoiding what would have turned out to be a much bigger mistake later.

Players are judged it seems, from year to year. Often it’s hard to replicate a good year. Like a pennant winning team, for personal records the same truth holds- you must have luck, no injuries, and record years.

The following year- team not as good as they don’t have the same luck, don’t get same breaks, etc. well, same for the individual.


My point- you can extend but expect up and down years doing the contract. It’s simple nature.

Therefore, it’s a hit and miss at best.

This game seems to work towards the recency bias, if the player is coming off a good year they seem to always get paid as if that year is going to continue to eternity.

[C-Unit]

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

This right here is what I expected to be the crux of the discussion. And it is a very good discussion.

Good discussion. I’d lock up Winn. Current GG, will only hit better. With JJ at second, may be the next Ozzie/Herr.

I'd lock up Winn also. I would hate if by the time we are winning again Winn is on the cusp of free agency.

[ecleme22]

Regarding the "wait for them to earn it" philosophy, as much as CT liked to hate on the Cardinals having extended DeJong for 6 yrs./$26 million after his rookie year, consider what it would have been if they had waited until after the 2019 season when he hit 30 HRs, went to the ASG, and was a top defensive SS.

They could have been talking extending him for 6 years at that point for $100 million or so.

So a tiny early extension paid off in avoiding what would have turned out to be a much bigger mistake later.

Your argument is “well maybe the org would be dumber if they waited.”

[sikeston bulldog2]

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

This right here is what I expected to be the crux of the discussion. And it is a very good discussion.

Good discussion. I’d lock up Winn. Current GG, will only hit better. With JJ at second, may be the next Ozzie/Herr.

I'd lock up Winn also. I would hate if by the time we are winning again Winn is on the cusp of free agency.

I hear ya. Not only do you make a commitment, from both team and olayer, you demonstrate to the team, fans, and other league players, that you are willing to commit.

That security may be important to some.

[mattmitchl44]

Regarding the "wait for them to earn it" philosophy, as much as CT liked to hate on the Cardinals having extended DeJong for 6 yrs./$26 million after his rookie year, consider what it would have been if they had waited until after the 2019 season when he hit 30 HRs, went to the ASG, and was a top defensive SS.

They could have been talking extending him for 6 years at that point for $100 million or so.

So a tiny early extension paid off in avoiding what would have turned out to be a much bigger mistake later.

Your argument is “well maybe the org would be dumber if they waited.”

My argument is that, if you're going to consider "alternative history," you should think about all alternative histories.

It has been argued that DeJong was the poster child for why it's better off to go year -to-year rather than commit long term early.

What they did actually do, as "bad" as some think it was, was likely the second best path they could have taken because they got such a cheap long term extension done early.

It's almost impossible for a team to "lose big" when doing these long term extensions for young players if they can get them done at the right price point.

[rockondlouie]

And if they crash & burn, then your payroll is screwed.

Not at $6, $7 million a year. That's next to nothing for the team.

Plus no agent worth two cents is letting his client sign a "team-friendly" deal, that's wish casting on your part matt.

They do all the time.

If you offer Burleson like 4 yrs./$24 million ($6 million AAV) with a team option year at $10 million, that kind of guaranteed money is potentially huge for him - that's potentially "generational wealth" with no risk - but negligible risk for the team.

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

If you feel they're only worth $6M-$7M (WAY TOO LOW A GUESS IMO), then why not just go through ARB giving you payroll insurance in case 1) they've already peaked and have no more upside and 2) injuries?

And agents do NOT sign lowball extensions like you mention for quality players "all the time".

The players you mention are average players, not all-stars and likely never going to be.

The ONLY player I'd even consider an early extension for is JJW and only IF he's everything we hope he'll be.

Finally, I'd rather wait till these average players EARN IT than hand them terrible extensions that could blow up BDWJr's SMALL ALREADY PAYROLL.

Your assuming these players are all going to have an upward trajection, a risky move that could mess up payroll for years.

Again, none of the players you mention are ready for extensions, perhaps in a year or two IF they continue to improve.

[ecleme22]

Regarding the "wait for them to earn it" philosophy, as much as CT liked to hate on the Cardinals having extended DeJong for 6 yrs./$26 million after his rookie year, consider what it would have been if they had waited until after the 2019 season when he hit 30 HRs, went to the ASG, and was a top defensive SS.

They could have been talking extending him for 6 years at that point for $100 million or so.

So a tiny early extension paid off in avoiding what would have turned out to be a much bigger mistake later.

Your argument is “well maybe the org would be dumber if they waited.”

My argument is that, if you're going to consider "alternative history," you should think about all alternative histories.

It has been argued that DeJong was the poster child for why it's better off to go year -to-year rather than commit long term early.

What they did actually do, as "bad" as some think it was, was likely the second best path they could have taken because they got such a cheap long term extension done early.

It's almost impossible for a team to "lose big" when doing these long term extensions for young players if they can get them done at the right price point.

Well you lose in flexibility to move on from a player. Also, when you invest in a prize pig, you’re not going to add to the roster that can potentially cut that pigs playing time.


When you go year to year, then maybe Paul’s first year of arb, he’s awarded 12mil. But THAT means his market value is around that, so if you want to trade him you can.

Of course there are exceptions. If you can trick an agent of a star player (Acuna) to sign low contract, cool.


But going year to year on everyone else is fine…

[mattmitchl44]

And if they crash & burn, then your payroll is screwed.

Not at $6, $7 million a year. That's next to nothing for the team.

Plus no agent worth two cents is letting his client sign a "team-friendly" deal, that's wish casting on your part matt.

They do all the time.

If you offer Burleson like 4 yrs./$24 million ($6 million AAV) with a team option year at $10 million, that kind of guaranteed money is potentially huge for him - that's potentially "generational wealth" with no risk - but negligible risk for the team.

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

If you feel they're only worth $6M-$7M (WAY TOO LOW A GUESS IMO), then why not just go through ARB giving you payroll insurance in case 1) they've already peaked and have no more upside and 2) injuries?

And agents do NOT sign lowball extensions like you mention for quality players "all the time".

The players you mention are average players, not all-stars and likely never going to be.

The ONLY player I'd even consider an early extension for is JJW and only IF he's everything we hope he'll be.

Finally, I'd rather wait till these average players EARN IT than hand them terrible extensions that could blow up BDWJr's SMALL ALREADY PAYROLL.

Your assuming these players are all going to have an upward trajection, a risky move that could mess up payroll for years.

Again, none of the players you mention are ready for extensions, perhaps in a year or two IF they continue to improve.

Again, for small AAV extensions, Burleson, Herrera, etc. don't need to be on upward trajectories. If they are just solid, average 2+ fWAR players for 4 or 5 years at $6, 7 million a year, that is a win for the team.

If the player is not interested in doing a long term extension at a price point like that, fine, but if the team projects them as a solid 2+ fWAR player they should make the offer and let them say no.

[ecleme22]

And if they crash & burn, then your payroll is screwed.

Not at $6, $7 million a year. That's next to nothing for the team.

Plus no agent worth two cents is letting his client sign a "team-friendly" deal, that's wish casting on your part matt.

They do all the time.

If you offer Burleson like 4 yrs./$24 million ($6 million AAV) with a team option year at $10 million, that kind of guaranteed money is potentially huge for him - that's potentially "generational wealth" with no risk - but negligible risk for the team.

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

If you feel they're only worth $6M-$7M (WAY TOO LOW A GUESS IMO), then why not just go through ARB giving you payroll insurance in case 1) they've already peaked and have no more upside and 2) injuries?

And agents do NOT sign lowball extensions like you mention for quality players "all the time".

The players you mention are average players, not all-stars and likely never going to be.

The ONLY player I'd even consider an early extension for is JJW and only IF he's everything we hope he'll be.

Finally, I'd rather wait till these average players EARN IT than hand them terrible extensions that could blow up BDWJr's SMALL ALREADY PAYROLL.

Your assuming these players are all going to have an upward trajection, a risky move that could mess up payroll for years.

Again, none of the players you mention are ready for extensions, perhaps in a year or two IF they continue to improve.

Again, for small AAV extensions, Burleson, Herrera, etc. don't need to be on upward trajectories. If they are just solid, average 2+ fWAR players for 4 or 5 years at $6, 7, 8 million a year, that is a win for the team.

If the player is not interested in doing a long term extension at a price point like that, fine, but if the team projects them as a solid 2+ fWAR player they should make the offer and let them say no.

And what happens if it’s not done?

Also, AB has never earned a 2 WAR

[mattmitchl44]

And if they crash & burn, then your payroll is screwed.

Not at $6, $7 million a year. That's next to nothing for the team.

Plus no agent worth two cents is letting his client sign a "team-friendly" deal, that's wish casting on your part matt.

They do all the time.

If you offer Burleson like 4 yrs./$24 million ($6 million AAV) with a team option year at $10 million, that kind of guaranteed money is potentially huge for him - that's potentially "generational wealth" with no risk - but negligible risk for the team.

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

If you feel they're only worth $6M-$7M (WAY TOO LOW A GUESS IMO), then why not just go through ARB giving you payroll insurance in case 1) they've already peaked and have no more upside and 2) injuries?

And agents do NOT sign lowball extensions like you mention for quality players "all the time".

The players you mention are average players, not all-stars and likely never going to be.

The ONLY player I'd even consider an early extension for is JJW and only IF he's everything we hope he'll be.

Finally, I'd rather wait till these average players EARN IT than hand them terrible extensions that could blow up BDWJr's SMALL ALREADY PAYROLL.

Your assuming these players are all going to have an upward trajection, a risky move that could mess up payroll for years.

Again, none of the players you mention are ready for extensions, perhaps in a year or two IF they continue to improve.

Again, for small AAV extensions, Burleson, Herrera, etc. don't need to be on upward trajectories. If they are just solid, average 2+ fWAR players for 4 or 5 years at $6, 7, 8 million a year, that is a win for the team.

If the player is not interested in doing a long term extension at a price point like that, fine, but if the team projects them as a solid 2+ fWAR player they should make the offer and let them say no.

And what happens if it’s not done?

Also, AB has never earned a 2 WAR

Burleson was 2.1 fWAR last year. Herrera was 2.7.

You go year -to-year. But you don't have them under team control/contract for their age 30, 31 seasons, maybe not even age 29. So if make it to FA and you decide you want them back, it will cost you more like $12-$15 million a year.

[ecleme22]

And if they crash & burn, then your payroll is screwed.

Not at $6, $7 million a year. That's next to nothing for the team.

Plus no agent worth two cents is letting his client sign a "team-friendly" deal, that's wish casting on your part matt.

They do all the time.

If you offer Burleson like 4 yrs./$24 million ($6 million AAV) with a team option year at $10 million, that kind of guaranteed money is potentially huge for him - that's potentially "generational wealth" with no risk - but negligible risk for the team.

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

If you feel they're only worth $6M-$7M (WAY TOO LOW A GUESS IMO), then why not just go through ARB giving you payroll insurance in case 1) they've already peaked and have no more upside and 2) injuries?

And agents do NOT sign lowball extensions like you mention for quality players "all the time".

The players you mention are average players, not all-stars and likely never going to be.

The ONLY player I'd even consider an early extension for is JJW and only IF he's everything we hope he'll be.

Finally, I'd rather wait till these average players EARN IT than hand them terrible extensions that could blow up BDWJr's SMALL ALREADY PAYROLL.

Your assuming these players are all going to have an upward trajection, a risky move that could mess up payroll for years.

Again, none of the players you mention are ready for extensions, perhaps in a year or two IF they continue to improve.

Again, for small AAV extensions, Burleson, Herrera, etc. don't need to be on upward trajectories. If they are just solid, average 2+ fWAR players for 4 or 5 years at $6, 7, 8 million a year, that is a win for the team.

If the player is not interested in doing a long term extension at a price point like that, fine, but if the team projects them as a solid 2+ fWAR player they should make the offer and let them say no.

And what happens if it’s not done?

Also, AB has never earned a 2 WAR

Burleson was 2.1 fWAR last year. Herrera was 2.7.

Burleson has a career 2.2 WAR according to BBR

[mattmitchl44]

And if they crash & burn, then your payroll is screwed.

Not at $6, $7 million a year. That's next to nothing for the team.

Plus no agent worth two cents is letting his client sign a "team-friendly" deal, that's wish casting on your part matt.

They do all the time.

If you offer Burleson like 4 yrs./$24 million ($6 million AAV) with a team option year at $10 million, that kind of guaranteed money is potentially huge for him - that's potentially "generational wealth" with no risk - but negligible risk for the team.

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

If you feel they're only worth $6M-$7M (WAY TOO LOW A GUESS IMO), then why not just go through ARB giving you payroll insurance in case 1) they've already peaked and have no more upside and 2) injuries?

And agents do NOT sign lowball extensions like you mention for quality players "all the time".

The players you mention are average players, not all-stars and likely never going to be.

The ONLY player I'd even consider an early extension for is JJW and only IF he's everything we hope he'll be.

Finally, I'd rather wait till these average players EARN IT than hand them terrible extensions that could blow up BDWJr's SMALL ALREADY PAYROLL.

Your assuming these players are all going to have an upward trajection, a risky move that could mess up payroll for years.

Again, none of the players you mention are ready for extensions, perhaps in a year or two IF they continue to improve.

Again, for small AAV extensions, Burleson, Herrera, etc. don't need to be on upward trajectories. If they are just solid, average 2+ fWAR players for 4 or 5 years at $6, 7, 8 million a year, that is a win for the team.

If the player is not interested in doing a long term extension at a price point like that, fine, but if the team projects them as a solid 2+ fWAR player they should make the offer and let them say no.

And what happens if it’s not done?

Also, AB has never earned a 2 WAR

Burleson was 2.1 fWAR last year. Herrera was 2.7.

Burleson has a career 2.2 WAR according to BBR

He improved significantly in 2025.

Look - if you don't believe in him being a 2+ fWAR player going forward, then you don't give him an extension, and you should arguably be trying to trade high on him now.

[rockondlouie]

And if they crash & burn, then your payroll is screwed.

Not at $6, $7 million a year. That's next to nothing for the team.

Plus no agent worth two cents is letting his client sign a "team-friendly" deal, that's wish casting on your part matt.

They do all the time.

If you offer Burleson like 4 yrs./$24 million ($6 million AAV) with a team option year at $10 million, that kind of guaranteed money is potentially huge for him - that's potentially "generational wealth" with no risk - but negligible risk for the team.

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

If you feel they're only worth $6M-$7M (WAY TOO LOW A GUESS IMO), then why not just go through ARB giving you payroll insurance in case 1) they've already peaked and have no more upside and 2) injuries?

And agents do NOT sign lowball extensions like you mention for quality players "all the time".

The players you mention are average players, not all-stars and likely never going to be.

The ONLY player I'd even consider an early extension for is JJW and only IF he's everything we hope he'll be.

Finally, I'd rather wait till these average players EARN IT than hand them terrible extensions that could blow up BDWJr's SMALL ALREADY PAYROLL.

Your assuming these players are all going to have an upward trajection, a risky move that could mess up payroll for years.

Again, none of the players you mention are ready for extensions, perhaps in a year or two IF they continue to improve.

Again, for small AAV extensions, Burleson, Herrera, etc. don't need to be on upward trajectories. If they are just solid, average 2+ fWAR players for 4 or 5 years at $6, 7 million a year, that is a win for the team.

If the player is not interested in doing a long term extension at a price point like that, fine, but if the team projects them as a solid 2+ fWAR player they should make the offer and let them say no.

We've been down this road before matt (re: the Braves), I'm never going to be a fan of giving extensions to players w/one-two-three years of MLB experience unless they've proved to be well above average, actually closer to being all-star players.

For every A. Pujols great extension you can find players who've flopped, and even the great Pujols didn't get his extension until after his THIRD SEASON!

And all Albert had done for those three years was slash .334 .412 .613 1.025, hit 114 HR's, drive in 381 runs while winning ROY, two silver sluggers, two all star appearances and two MVP runner-up seasons plus a fourth place finish to boot!

NOW that's a player you easily hand an extension too.

Not Winn, Burleson, Libby type players.

(And I still think you've thrown out really low extension figures to support your argument that aren't realistic)

JMO

[ecleme22]

And if they crash & burn, then your payroll is screwed.

Not at $6, $7 million a year. That's next to nothing for the team.

Plus no agent worth two cents is letting his client sign a "team-friendly" deal, that's wish casting on your part matt.

They do all the time.

If you offer Burleson like 4 yrs./$24 million ($6 million AAV) with a team option year at $10 million, that kind of guaranteed money is potentially huge for him - that's potentially "generational wealth" with no risk - but negligible risk for the team.

NO EXTENSIONS until they've earned it

Waiting for them to "earn it" is how you end up paying a lot more for past production rather than future production.

If you feel they're only worth $6M-$7M (WAY TOO LOW A GUESS IMO), then why not just go through ARB giving you payroll insurance in case 1) they've already peaked and have no more upside and 2) injuries?

And agents do NOT sign lowball extensions like you mention for quality players "all the time".

The players you mention are average players, not all-stars and likely never going to be.

The ONLY player I'd even consider an early extension for is JJW and only IF he's everything we hope he'll be.

Finally, I'd rather wait till these average players EARN IT than hand them terrible extensions that could blow up BDWJr's SMALL ALREADY PAYROLL.

Your assuming these players are all going to have an upward trajection, a risky move that could mess up payroll for years.

Again, none of the players you mention are ready for extensions, perhaps in a year or two IF they continue to improve.

Again, for small AAV extensions, Burleson, Herrera, etc. don't need to be on upward trajectories. If they are just solid, average 2+ fWAR players for 4 or 5 years at $6, 7, 8 million a year, that is a win for the team.

If the player is not interested in doing a long term extension at a price point like that, fine, but if the team projects them as a solid 2+ fWAR player they should make the offer and let them say no.

And what happens if it’s not done?

Also, AB has never earned a 2 WAR

Burleson was 2.1 fWAR last year. Herrera was 2.7.

Burleson has a career 2.2 WAR according to BBR

He improved significantly in 2025.

Look - if you don't believe in him being a 2+ fWAR player going forward, then you don't give him an extension, and you should arguably be trying to trade high on him now.

He improved in 2025 to a 2.1 WAR...nearly your baseline for extensions.

And he will be on the team in 2026. Does he need to be extended? No. If no extension, does he need to be traded? No.

Sometimes you can have a homegrown player on the team without worrying about marrying him or divorcing him...