Jrue Holiday’s Contract Extension

[Moranis]

My statement was absolutely about the 25-26 season and beyond.  Next year if Jrue opts in, Boston has about 200 million and 11 players under contract (the top 6, PP, Springer, Brissett, Hauser, Walsh).  Even if Jrue drops down 15 million, the team will probably not avoid the 2nd apron, but if it does it will be so close to it, it won't matter all that much practically.

In 25-26, the only 4 players under contract are Jaylen at 53 million, Porzingis at 31 million, PP at 7 million, and Walsh at 2 million.  The cap is currently projected at 155 million, which puts Tatum extension at just over 54 million.  Let's say White gets a Zinger type contract so 32 million.  So that leaves about 40 million to fill out the roster and stay below the 2nd apron.  It may be inevitable that year, but it is not in 26-27 if Jrue is small enough.  That is where the benefit lies, i.e. getting out of the 2nd apron sooner. 

[Roy H.]

I don't think he'll decline his player option because I don't think he'll get as much if he hits free agency, simply because of his age - who is going to give Holiday a long-term contract that competes with just claiming his player option?

What if the Celtics told him to decline and take a 4-year, $100 million deal? Sure, he'd be giving up $15 million initially, but he's essentially getting that and then some back at the end.

That's what I see happening – a Paul Pierce-style option decline for a longer-term contract.

https://www.espn.com/nba/story/_/id/5384171

that is worse for Boston long term.  It is much better to be 39.4 next year and just add 3 years 60 million on end in that scenario.

Has anybody done the math on this?  I know I haven't.  There's a world where that $39 million next year is worse, because we're paying an exorbitant amount of tax.  Minimizing the first year of the contract and spreading out the cap hit over multiple years is what the team preferred with Porzingis.  I'm not sure if it's the better call with Jrue or not.

It has less to do with the tax paid by ownership and more to do with the fact that White (UFA) and Tatum (player option) will be up for new deals in 2025-2026 and the priority should be giving White, in particular, the most competitive offer possible.

Again, though, it's a math calculation.  Using made up numbers, let's say that cutting Jrue's salary next season by $15 million yields $40 million in tax savings. 

If Wyc applies that $40 million in '25-'26, does that make it easier to retain White?

There are other considerations, such as repeater tax, and eventually, second apron repeater penalties.  But, without running the math -- which includes significant increases to the salary cap the next two years -- people seem to be stating guesses as fact.

So I had a big post eaten up by being logged out, but the upshot is that I'm not convinced that it makes a huge difference in the context of the two deals being discussed - namely between 4/100 and 39+ a smaller 3-year deal.

However, If we believe Jrue can be extended on something like a 3/60 or 4/80, then the team is in a great position going forward, but I don't think Holiday accepts 3/60 and I don't think the team wants to offer him a four-year deal.

Just to recap where I sit very briefly:

If we believe that the front office wants an extension done this season, I feel like the C's will probably offer something around/below the three-year, 75-80 deal being discussed put on the table, let alone maxing him out at 4-years/100.

I don't think it's four years because: 1) he's not a 32-year-old Pierce, and 2) he's not playing under a cap system where signing an extension creates a significant amount of flexibility for the Celtics - in fact, the most flexible move for the team, as other posters have said, is for him to opt into the PO and then take a smaller deal in free agency after next season, but that's a move that entirely favours the front office, rather than the player, so unlikely.

The team should offer him a four-year deal as long as the value doesn’t increase from year to year.  If he’s cooked in the final year, that’s the cost of doing business, and the cap/tax lines will be around 35% higher than they are today so it will be a little easier to absorb $20-25 million of dead space on the roster, or even $30 million, frankly.  It’s a much lower downside if he’s cooked in four years than if he walks this summer.

I wonder if he'd go for something like this:

2025:  $25 million
2026:  $25 million
2027:  $23 million
2028:  $21 million

So, four years, $94 million.  It's essentially a 3 year, $54 million extension, which seems fair for a soon to be 34 year old.

[Kernewek]

I don't think he'll decline his player option because I don't think he'll get as much if he hits free agency, simply because of his age - who is going to give Holiday a long-term contract that competes with just claiming his player option?

What if the Celtics told him to decline and take a 4-year, $100 million deal? Sure, he'd be giving up $15 million initially, but he's essentially getting that and then some back at the end.

That's what I see happening – a Paul Pierce-style option decline for a longer-term contract.

https://www.espn.com/nba/story/_/id/5384171

that is worse for Boston long term.  It is much better to be 39.4 next year and just add 3 years 60 million on end in that scenario.

Has anybody done the math on this?  I know I haven't.  There's a world where that $39 million next year is worse, because we're paying an exorbitant amount of tax.  Minimizing the first year of the contract and spreading out the cap hit over multiple years is what the team preferred with Porzingis.  I'm not sure if it's the better call with Jrue or not.

It has less to do with the tax paid by ownership and more to do with the fact that White (UFA) and Tatum (player option) will be up for new deals in 2025-2026 and the priority should be giving White, in particular, the most competitive offer possible.

Again, though, it's a math calculation.  Using made up numbers, let's say that cutting Jrue's salary next season by $15 million yields $40 million in tax savings. 

If Wyc applies that $40 million in '25-'26, does that make it easier to retain White?

There are other considerations, such as repeater tax, and eventually, second apron repeater penalties.  But, without running the math -- which includes significant increases to the salary cap the next two years -- people seem to be stating guesses as fact.

So I had a big post eaten up by being logged out, but the upshot is that I'm not convinced that it makes a huge difference in the context of the two deals being discussed - namely between 4/100 and 39+ a smaller 3-year deal.

However, If we believe Jrue can be extended on something like a 3/60 or 4/80, then the team is in a great position going forward, but I don't think Holiday accepts 3/60 and I don't think the team wants to offer him a four-year deal.

Just to recap where I sit very briefly:

If we believe that the front office wants an extension done this season, I feel like the C's will probably offer something around/below the three-year, 75-80 deal being discussed put on the table, let alone maxing him out at 4-years/100.

I don't think it's four years because: 1) he's not a 32-year-old Pierce, and 2) he's not playing under a cap system where signing an extension creates a significant amount of flexibility for the Celtics - in fact, the most flexible move for the team, as other posters have said, is for him to opt into the PO and then take a smaller deal in free agency after next season, but that's a move that entirely favours the front office, rather than the player, so unlikely.

The team should offer him a four-year deal as long as the value doesn’t increase from year to year.  If he’s cooked in the final year, that’s the cost of doing business, and the cap/tax lines will be around 35% higher than they are today so it will be a little easier to absorb $20-25 million of dead space on the roster, or even $30 million, frankly.  It’s a much lower downside if he’s cooked in four years than if he walks this summer.

I wonder if he'd go for something like this:

2025:  $25 million
2026:  $25 million
2027:  $23 million
2028:  $21 million

So, four years, $94 million.  It's essentially a 3 year, $54 million extension, which seems fair for a soon to be 34 year old.

This makes sense if we are advocating from the position of Holiday & his agent. As a fan, it makes sense to me, but I am still not certain the Celtics would agree to it and I'm certain their starting offer will be lower.

It's possible that the deal looks like this in the end, of course: buoyed by the fact that Holiday's agent can say 'look, Jrue came in and replaced the DPOY whilst making the world-beating offense even better: you've said in public that the old team had to be blown up for the team to win a championship, so do you think this contract extension is a fair price to pay for a championship? If not, what would you like me to tell my client?'

[otherdave]

I think Jrue's game (at least offensively) will age well like Horford's has.  Neither player's game ever depended on elite athleticism like Blake's did.

Defensive might become an issue at some point, but Jrue is just so crafty.

I might feel comfortable offering him a four year deal at the 94 million that Roy suggested.

[tenn_smoothie]

Good Lord, the league has lost it's mind. What possible reason would a person turn down $40M, especially given the millions Holiday has already made during his career? Is his life going to see significant change if he opts for $25M per for three seasons instead? I know, I know, it's the insane world of pro sports that we now live in, but some realistic perspective would be in order here. Of course, this same craziness is now trickling down into college and even high school. I find it very sad watching the slow death of amateur athletics. Pure greed from many sources has fueled this disaster.

Do you often take less money from your employer in order to do your job?

Typical response - Of course not, but you are comparing different universes in terms of money here, so that argument (which I ALWAYS hear) is missing the point. Apples & Oranges.

[tenn_smoothie]

Good Lord, the league has lost it's mind. What possible reason would a person turn down $40M, especially given the millions Holiday has already made during his career? Is his life going to see significant change if he opts for $25M per for three seasons instead? I know, I know, it's the insane world of pro sports that we now live in, but some realistic perspective would be in order here. Of course, this same craziness is now trickling down into college and even high school. I find it very sad watching the slow death of amateur athletics. Pure greed from many sources has fueled this disaster.

Team owners/the league have all the control of the money. They could take lower money TV deals (likely with channels that would give a better experience for fans) or charge less for seats, and both their profits and player salaries would go down as a result. Players don't have that sort of control. And owners won't do any of that, because they want all the money they can get.

Being mad at players for wanting their share of the billions that owners make from them just seems misplaced.

I was not placing blame on only the players. Notice I said, "the league has lost it's mind" and "pure greed from many sources has fueled this disaster. My comments regarding Holiday were more about the general insanity of the huge amounts of money in pro sports, not about his character.

[keevsnick]

I don't think he'll decline his player option because I don't think he'll get as much if he hits free agency, simply because of his age - who is going to give Holiday a long-term contract that competes with just claiming his player option?

What if the Celtics told him to decline and take a 4-year, $100 million deal? Sure, he'd be giving up $15 million initially, but he's essentially getting that and then some back at the end.

That's what I see happening – a Paul Pierce-style option decline for a longer-term contract.

https://www.espn.com/nba/story/_/id/5384171

that is worse for Boston long term.  It is much better to be 39.4 next year and just add 3 years 60 million on end in that scenario.

Has anybody done the math on this?  I know I haven't.  There's a world where that $39 million next year is worse, because we're paying an exorbitant amount of tax.  Minimizing the first year of the contract and spreading out the cap hit over multiple years is what the team preferred with Porzingis.  I'm not sure if it's the better call with Jrue or not.

It has less to do with the tax paid by ownership and more to do with the fact that White (UFA) and Tatum (player option) will be up for new deals in 2025-2026 and the priority should be giving White, in particular, the most competitive offer possible.

Again, though, it's a math calculation.  Using made up numbers, let's say that cutting Jrue's salary next season by $15 million yields $40 million in tax savings. 

If Wyc applies that $40 million in '25-'26, does that make it easier to retain White?

There are other considerations, such as repeater tax, and eventually, second apron repeater penalties.  But, without running the math -- which includes significant increases to the salary cap the next two years -- people seem to be stating guesses as fact.

So I had a big post eaten up by being logged out, but the upshot is that I'm not convinced that it makes a huge difference in the context of the two deals being discussed - namely between 4/100 and 39+ a smaller 3-year deal.

However, If we believe Jrue can be extended on something like a 3/60 or 4/80, then the team is in a great position going forward, but I don't think Holiday accepts 3/60 and I don't think the team wants to offer him a four-year deal.

Just to recap where I sit very briefly:

If we believe that the front office wants an extension done this season, I feel like the C's will probably offer something around/below the three-year, 75-80 deal being discussed put on the table, let alone maxing him out at 4-years/100.

I don't think it's four years because: 1) he's not a 32-year-old Pierce, and 2) he's not playing under a cap system where signing an extension creates a significant amount of flexibility for the Celtics - in fact, the most flexible move for the team, as other posters have said, is for him to opt into the PO and then take a smaller deal in free agency after next season, but that's a move that entirely favours the front office, rather than the player, so unlikely.

The team should offer him a four-year deal as long as the value doesn’t increase from year to year.  If he’s cooked in the final year, that’s the cost of doing business, and the cap/tax lines will be around 35% higher than they are today so it will be a little easier to absorb $20-25 million of dead space on the roster, or even $30 million, frankly.  It’s a much lower downside if he’s cooked in four years than if he walks this summer.

I wonder if he'd go for something like this:

2025:  $25 million
2026:  $25 million
2027:  $23 million
2028:  $21 million

So, four years, $94 million.  It's essentially a 3 year, $54 million extension, which seems fair for a soon to be 34 year old.

Something in the 4/100 range gives the c's at least a shot of staying below the second apron next year.  I don
t care about Wyc's tax money, but not having the draft pick froze would be nice.

[Phantom255x]

20 oz. soda bottles which are typically $2 in most stores costs $8 at TD Garden

Keep the crew together 

[bdm860]

I don't think he'll decline his player option because I don't think he'll get as much if he hits free agency, simply because of his age - who is going to give Holiday a long-term contract that competes with just claiming his player option?

What if the Celtics told him to decline and take a 4-year, $100 million deal? Sure, he'd be giving up $15 million initially, but he's essentially getting that and then some back at the end.

That's what I see happening – a Paul Pierce-style option decline for a longer-term contract.

https://www.espn.com/nba/story/_/id/5384171

that is worse for Boston long term.  It is much better to be 39.4 next year and just add 3 years 60 million on end in that scenario.

Has anybody done the math on this?  I know I haven't.  There's a world where that $39 million next year is worse, because we're paying an exorbitant amount of tax.  Minimizing the first year of the contract and spreading out the cap hit over multiple years is what the team preferred with Porzingis.  I'm not sure if it's the better call with Jrue or not.

It has less to do with the tax paid by ownership and more to do with the fact that White (UFA) and Tatum (player option) will be up for new deals in 2025-2026 and the priority should be giving White, in particular, the most competitive offer possible.

Again, though, it's a math calculation.  Using made up numbers, let's say that cutting Jrue's salary next season by $15 million yields $40 million in tax savings. 

If Wyc applies that $40 million in '25-'26, does that make it easier to retain White?

There are other considerations, such as repeater tax, and eventually, second apron repeater penalties.  But, without running the math -- which includes significant increases to the salary cap the next two years -- people seem to be stating guesses as fact.

So I had a big post eaten up by being logged out, but the upshot is that I'm not convinced that it makes a huge difference in the context of the two deals being discussed - namely between 4/100 and 39+ a smaller 3-year deal.

However, If we believe Jrue can be extended on something like a 3/60 or 4/80, then the team is in a great position going forward, but I don't think Holiday accepts 3/60 and I don't think the team wants to offer him a four-year deal.

Just to recap where I sit very briefly:

If we believe that the front office wants an extension done this season, I feel like the C's will probably offer something around/below the three-year, 75-80 deal being discussed put on the table, let alone maxing him out at 4-years/100.

I don't think it's four years because: 1) he's not a 32-year-old Pierce, and 2) he's not playing under a cap system where signing an extension creates a significant amount of flexibility for the Celtics - in fact, the most flexible move for the team, as other posters have said, is for him to opt into the PO and then take a smaller deal in free agency after next season, but that's a move that entirely favours the front office, rather than the player, so unlikely.

The team should offer him a four-year deal as long as the value doesn’t increase from year to year.  If he’s cooked in the final year, that’s the cost of doing business, and the cap/tax lines will be around 35% higher than they are today so it will be a little easier to absorb $20-25 million of dead space on the roster, or even $30 million, frankly.  It’s a much lower downside if he’s cooked in four years than if he walks this summer.

I wonder if he'd go for something like this:

2025:  $25 million
2026:  $25 million
2027:  $23 million
2028:  $21 million

So, four years, $94 million.  It's essentially a 3 year, $54 million extension, which seems fair for a soon to be 34 year old.

Not a lot of older guards get big contracts to compare, but the recent market off the top of my head:

In 2021, Chris Paul $120m/4yrs ($84m guaranteed), going into the season when he'd be 36.
In 2021, Mike Conley $68m/3yrs ($58m guaranteed), going into the season when he'd be 34.
In 2024, Mike Conley $21m/2yrs extension, in the middle of this season when he's 36.
In 2021, Kyle Lowry $85m/3yrs, going into the season when he'd be 35.

So 3 years ago (also when Jrue signed his current deal), 6' guards between ages 34-36 were getting between $58m-$85m for 3 years.  Cap has gone up 20% since then.   $54m/3yrs might be a little on the low for a 35 year old 6'4" guard.  He's not as accomplished as Paul or Lowry (but a combination of hindsight and koolaid says Jrue will be better from ages 35-38 than Lowry), but it's probably fair to put him closer to Mike Conley.

Now if the team could get Jrue for Mike Conley extension money, that would be awesome.

[Kernewek]

Good Lord, the league has lost it's mind. What possible reason would a person turn down $40M, especially given the millions Holiday has already made during his career? Is his life going to see significant change if he opts for $25M per for three seasons instead? I know, I know, it's the insane world of pro sports that we now live in, but some realistic perspective would be in order here. Of course, this same craziness is now trickling down into college and even high school. I find it very sad watching the slow death of amateur athletics. Pure greed from many sources has fueled this disaster.

Do you often take less money from your employer in order to do your job?

Typical response - Of course not, but you are comparing different universes in terms of money here, so that argument (which I ALWAYS hear) is missing the point. Apples & Oranges.

Perhaps you should entertain the idea that you always hear the argument because you are not considering it rationally, rather than everyone else 'always' missing your point.

[tenn_smoothie]

Good Lord, the league has lost it's mind. What possible reason would a person turn down $40M, especially given the millions Holiday has already made during his career? Is his life going to see significant change if he opts for $25M per for three seasons instead? I know, I know, it's the insane world of pro sports that we now live in, but some realistic perspective would be in order here. Of course, this same craziness is now trickling down into college and even high school. I find it very sad watching the slow death of amateur athletics. Pure greed from many sources has fueled this disaster.

Do you often take less money from your employer in order to do your job?

Typical response - Of course not, but you are comparing different universes in terms of money here, so that argument (which I ALWAYS hear) is missing the point. Apples & Oranges.

Perhaps you should entertain the idea that you always hear the argument because you are not considering it rationally, rather than everyone else 'always' missing your point.

Actually, there were a few responses here that understood the point I was making about the fallacy of comparing salaries that are worlds apart.

[Kernewek]

Good Lord, the league has lost it's mind. What possible reason would a person turn down $40M, especially given the millions Holiday has already made during his career? Is his life going to see significant change if he opts for $25M per for three seasons instead? I know, I know, it's the insane world of pro sports that we now live in, but some realistic perspective would be in order here. Of course, this same craziness is now trickling down into college and even high school. I find it very sad watching the slow death of amateur athletics. Pure greed from many sources has fueled this disaster.

Do you often take less money from your employer in order to do your job?

Typical response - Of course not, but you are comparing different universes in terms of money here, so that argument (which I ALWAYS hear) is missing the point. Apples & Oranges.

Perhaps you should entertain the idea that you always hear the argument because you are not considering it rationally, rather than everyone else 'always' missing your point.

Actually, there were a few responses here that understood the point I was making about the fallacy of comparing salaries that are worlds apart.

But it's not a fallacy, because your employment situations are directly comparable.