Jrue Holiday’s Contract Extension

[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

Oh definitely an extension is in the cards - I didn't realise he would be eligible for one in April, thought it was after the season ended - and it's a good point because Holiday's on the record wanting to be extended, the Celtics are going to have a difficult time replacing him if he leaves, and this is probably going to be his last big NBA contract. All points for Jrue to push for an extension.

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.

[Moranis]

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.

[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.

[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?

[BitterJim]

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.

[ozgod]

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?

I guess Tenn's objection is to the amounts being discussed...at some point anything over a certain amount gets tagged by our brains as "too much money" and we have trouble making a distinction between different amounts over that. So $25m seems the same as $40m - it's an obscene amount of money, especially if the player has already made millions. As fans we would hope he would be willing to take less "for the good of the team".

Of course for people who do have money, there are many different categories of "being rich"...someone with a net worth of $20m would not be able to make certain investments or acquire certain parcels of real estate as someone who has $100m. Just like that $100m guy might not be able to have access to certain investments as a $500m guy, like be an investor in a sports team for example. But it's all too much for our everyday person brains to comprehend 

And of course, salaries in the NBA are usually negotiated as a percentage of the salary cap, like a max contract is 35%, and the scale drops from there. So as the cap goes up the salaries they negotiate all go up based on that cap number. And the cap number goes up because the league itself is financially thriving. So if someone is going to take a discount, there would usually have to be a good reason why he would accept being paid like a lesser player would. Sometimes that might mean "for the good of the team", like Harden took a discount on his extension to help Daryl Morey sign more players, and on the expectation that 2 years later Daryl would return the favor. Of course we now all know Daryl did not - which is why it's understandable that these guys chase as much money as they can. Cold blooded business, this 

[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.

[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.

[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?

I guess Tenn's objection is to the amounts being discussed...at some point anything over a certain amount gets tagged by our brains as "too much money" and we have trouble making a distinction between different amounts over that. So $25m seems the same as $40m - it's an obscene amount of money, especially if the player has already made millions. As fans we would hope he would be willing to take less "for the good of the team".

Of course for people who do have money, there are many different categories of "being rich"...someone with a net worth of $20m would not be able to make certain investments or acquire certain parcels of real estate as someone who has $100m. Just like that $100m guy might not be able to have access to certain investments as a $500m guy, like be an investor in a sports team for example. But it's all too much for our everyday person brains to comprehend 

And of course, salaries in the NBA are usually negotiated as a percentage of the salary cap, like a max contract is 35%, and the scale drops from there. So as the cap goes up the salaries they negotiate all go up based on that cap number. And the cap number goes up because the league itself is financially thriving. So if someone is going to take a discount, there would usually have to be a good reason why he would accept being paid like a lesser player would. Sometimes that might mean "for the good of the team", like Harden took a discount on his extension to help Daryl Morey sign more players, and on the expectation that 2 years later Daryl would return the favor. Of course we now all know Daryl did not - which is why it's understandable that these guys chase as much money as they can. Cold blooded business, this 

I think this is true, and this is the best way I've seen to adjust for this disconnect:

A million seconds is 12 days.

A billion seconds is 31 years.

[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.

[ozgod]

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.

I did the math on next season but not on the ones after...I'm guessing Moranis was talking about in relation to having 4 years of $25m each vs 1st year of $40m and 3 years of $20m and picking between those two, because it's front loaded and as Kernewek said we have a lot of big player spend coming up, and probably because if Jrue is declining, have his lower numbers heading into the future to make it easier to offload him at that point. And I don't think I've ever met a fan that cares about the tax owners have to pay in any case 

And I think we would be a second apron team whether he's at $40m next season or $25m. Obviously a 4 year $20m a season would be the best option of the three 

Here's a snapshot of our cap next season, with guaranteed contracts, the options and the holds which came from Spotrac, I just converted it to Excel.

[ozgod]

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.

My guess is that it's the latter rather than the former that would inform any decisions about Jrue's extension. It's about how much flexibility Brad can have while operating as a second apron team for the next few years.

[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.

I did the math on next season but not on the ones after...I'm guessing Moranis was talking about in relation to having 4 years of $25m each vs 1st year of $40m and 3 years of $20m and picking between those two, because it's front loaded and as Kernewek said we have a lot of big player spend coming up, and probably because if Jrue is declining, have his lower numbers heading into the future to make it easier to offload him at that point. And I don't think I've ever met a fan that cares about the tax owners have to pay in any case 

And I think we would be a second apron team whether he's at $40m next season or $25m. Obviously a 4 year $20m a season would be the best option of the three 

Here's a snapshot of our cap next season, with guaranteed contracts, the options and the holds which came from Spotrac, I just converted it to Excel.

If Jrue took $15 million less, that seemingly could get us below the second apron, and would save tens of millions in tax. 

Just doing some very quick math in my head, we could pick up all of the options and bring back three free agents at a minimum salary, and be right at the second apron line if Drew agreed to a $15 million reduction in year one.

[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.

I won't have time to sit down with the data and see exactly where the line is until later in the week, unfortunately.

[Celtics2021]

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.