Derrick White, extends 4yrs/$125.9M

wade boggs chicken dinner

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As an intellectual exercise, people need to try and make a stronger case for why DWhite would be awesome on other teams. Everyone is searching for the evidence for why he'd be less valuable, to convince themselves it's really likely the Cs can re-sign him at $31/year.
DW is an all-NBA defensive player and an All-Star level player. There is no question that were he an UFA this summer, he'd get multiple max offers.

I don't know DW from Adam so I have no idea what he's thinking but my WAG is that DW isn't taking a max offer from a non-contender just to get paid. But there are several contenders who would be great fits - he would great in GSW (if they could work out a sign-and-trade), OKC (if they really wanted him, which I'm not sure they would do), NO, IND, etc. He would probably be happy playing 45+ minutes every night for Thibs too. :cool:

But fortunately he's not a UFA this summer and as BenHogan and others have mentioned, hopefully he's happy with the additional $120+M of guaranteed money plus a chance to win championships rather than playing out the final year of his contract and going through the FA process.

BTW, if he doesn't sign the extension, my guess is that he's gone, which would absolutely suck.
 

lovegtm

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BTW, if he doesn't sign the extension, my guess is that he's gone, which would absolutely suck.
Is this true? It might just mean he wants the Celtics to pay him a lot more than $31M/year. His potential starting salary in 2025 would be over $45M, with potential 8% raises. In addition, he could sign for 5 guaranteed years for what is almost certainly his last really big contract.

There's zero chance the Celtics would max him, and not much chance he'd ask for that. But we're talking about locking in $200M+ easily, as opposed to $125M, if you wait one season. With other bidders waiting in the wings. It's a pretty material difference.
 

InstaFace

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Is this true? It might just mean he wants the Celtics to pay him a lot more than $31M/year. His potential starting salary in 2025 would be over $45M, with potential 8% raises. In addition, he could sign for 5 guaranteed years for what is almost certainly his last really big contract.

There's zero chance the Celtics would max him, and not much chance he'd ask for that. But we're talking about locking in $200M+ easily, as opposed to $125M, if you wait one season. With other bidders waiting in the wings. It's a pretty material difference.
How sure are we that a White under contract for next year for his age-30 season, would view a 4-year extension through age 34, as being "his last big contract"? Jrue Holiday just got more than White would be getting, for Holiday's age 34-37 seasons. White's odometer is pretty low, his skillset one that should age well. And he'd have the ability to get the last year of that extension as a player option (3+1), so if he wants to terminate after age 33, he could do it, or even have it be 2+1, if he thinks that optimizes the value of his next contract.

He may well believe he'd get a max if he waits a year, in which case we're in deep trouble as far as keeping him. But if he thinks he'd end up in the $35-40 range, vs locking in $31-32 now (pending all-defense bump), it's probably a closer call financially than the above comparison might suggest.
 

wade boggs chicken dinner

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Is this true? It might just mean he wants the Celtics to pay him a lot more than $31M/year. His potential starting salary in 2025 would be over $45M, with potential 8% raises. In addition, he could sign for 5 guaranteed years for what is almost certainly his last really big contract.

There's zero chance the Celtics would max him, and not much chance he'd ask for that. But we're talking about locking in $200M+ easily, as opposed to $125M, if you wait one season. With other bidders waiting in the wings. It's a pretty material difference.
DW may not ask the Cs for a max, but if he goes to FA, my guess is that he'll get max offers.

And while I'd certainly be over the moon if Wyc agreed to sign DW for 5 years starting at $45M, I have to think there's a line somewhere. You'd know better than I would what the tax bills would be; not being a math guy, my only guess is that they would be north of outrageous.

I just don't see it being very likely that the Cs would be able to keep him if he doesn't sign an extension with the player option.
 

lovegtm

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DW may not ask the Cs for a max, but if he goes to FA, my guess is that he'll get max offers.

And while I'd certainly be over the moon if Wyc agreed to sign DW for 5 years starting at $45M, I have to think there's a line somewhere. You'd know better than I would what the tax bills would be; not being a math guy, my only guess is that they would be north of outrageous.

I just don't see it being very likely that the Cs would be able to keep him if he doesn't sign an extension with the player option.
They can keep him if they sign him for a higher number--it just means someone else would go.

It's almost better to table the cap discussions at this point, and see where things go this playoffs and next year. If they win 1-2 titles, a lot of things will change, for better and worse.
 

Eric Fernsten's Disco Mustache

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Most teams who are under the 2nd apron could work out a S&T, and Boston would likely go along with one in that scenario... [and]... take picks rather than nothing.
I... think you artificially limited the number of suitors by excluding S&Ts
I'm probably guilty as charged

Both because (i) which teams will have cap space to sign a >$30M UFA next summer is hard to predict, and (ii) job / parenthood / etc., I haven't gone very far down the rabbit hole of how many and which teams this might be

I will flag quickly, tho, that DWhite and his agent setting up a S&T next summer, in the scenario where Boston legit wants to resign him, has some real complications and risk. To pull it off they will have to
  1. Talk a team with >$30M in cap room (call this Team #1) into making White a serious offer as a UFA, without them finding out that White doesn't really want to go there
  2. Persuade their preferred team that does not have this room (call this Team #2) to make Boston a sign-and-trade offer
  3. While Boston and Team #2 are negotiating the potential sign-and-trade, they have to keep Boston from manipulating Team #1 into retracting their offer, since that would destroy Team #2s leverage
  4. Consummate the deal between Boston and Team #2 quickly, because free agency moves fast and neither Team #1 nor Team #2 are going to want to have >$30M of their cap space sitting in limbo while their fallback plans are signing with other teams
Obviously, this is doable, but it's not a slam dunk

And if it falls apart, and ~48 hours into free agency more or less no other franchises end up being a viable path, than White's options turn into (i) resign for the best offer Boston is willing to make, or (ii) accept an exception contract (somewhere in the $5-15M range) from a team that's over the cap. Call the second the Dennis Schroeder approach to free agency.

I dunno if this next is significant or not, but...

To my memory, most NBA sign-and-trades of the sort we're speculating about are either over lower-paid back end starter/rotation players, where the fungibility of contracts is higher and the stakes are lower. Or they involve superstars that have so much power that they can dictate terms to Teams. White kinda isn't in either category. Big contract. But he's not LeBron. Heck, as Dame found out when he tried to force his way to Miami, even being Dame wasn't enough of a big deal.
 

lovegtm

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I'm probably guilty as charged

Both because (i) which teams will have cap space to sign a >$30M UFA next summer is hard to predict, and (ii) job / parenthood / etc., I haven't gone very far down the rabbit hole of how many and which teams this might be

I will flag quickly, tho, that DWhite and his agent setting up a S&T next summer, in the scenario where Boston legit wants to resign him, has some real complications and risk. To pull it off they will have to
  1. Talk a team with >$30M in cap room (call this Team #1) into making White a serious offer as a UFA, without them finding out that White doesn't really want to go there
  2. Persuade their preferred team that does not have this room (call this Team #2) to make Boston a sign-and-trade offer
  3. While Boston and Team #2 are negotiating the potential sign-and-trade, they have to keep Boston from manipulating Team #1 into retracting their offer, since that would destroy Team #2s leverage
  4. Consummate the deal between Boston and Team #2 quickly, because free agency moves fast and neither Team #1 nor Team #2 are going to want to have >$30M of their cap space sitting in limbo while their fallback plans are signing with other teams
Obviously, this is doable, but it's not a slam dunk

And if it falls apart, and ~48 hours into free agency more or less no other franchises end up being a viable path, than White's options turn into (i) resign for the best offer Boston is willing to make, or (ii) accept an exception contract (somewhere in the $5-15M range) from a team that's over the cap. Call the second the Dennis Schroeder approach to free agency.

I dunno if this next is significant or not, but...

To my memory, most NBA sign-and-trades of the sort we're speculating about are either over lower-paid back end starter/rotation players, where the fungibility of contracts is higher and the stakes are lower. Or they involve superstars that have so much power that they can dictate terms to Teams. White kinda isn't in either category. Big contract. But he's not LeBron. Heck, as Dame found out when he tried to force his way to Miami, even being Dame wasn't enough of a big deal.
Agents do steps 1-4 all the time. The reason there are fewer S&Ts lately is that fewer stars hit free agency. When they do (Durant in 2019, Butler in 2019), the deals get done pretty easily, even between in-conference rivals like Philly and Miami.

You're overcomplicating this in order to feel better about Boston's chances of getting DWhite way below market. I want him below market too, and think there's a ~50% chance it happens, but I'm trying to be clear-eyed about NBA S&T mechanics.
 

Eric Fernsten's Disco Mustache

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You're overcomplicating this in order to feel better about Boston's chances of getting DWhite way below market.
You may well be right and I'm overcomplicating this. (It's been known to happen; just ask my wife).

From a place of kindness, tho, I'd caution against assuming you know *why* a stranger on the internet is (from your perspective) overcomplicating this




Agents do steps 1-4 all the time. The reason there are fewer S&Ts lately is that fewer stars hit free agency. When they do (Durant in 2019, Butler in 2019), the deals get done pretty easily, even between in-conference rivals like Philly and Miami.

Mmmmmm.... kinda

When Jimmy Butler wanted out of Philly in 2019 one key to the sign-and-trade negotiation was that Philly wanted him gone. He'd been clashing with Brett Brown and Ben Simmons, and the front office threw their lot in with Simmons and Tobias Harris. Is a sign-and-trade easier when the player's current team wants that guy gone? Sure. As you've said upthread, at that point the choice is between something or nothing. And the former looks better.

When Kevin Durant hit free agency in 2019 the Brooklyn Nets were sitting on >$30M of almost-max cap space and had little trouble moving a few small contracts to get all the way there. So, in effect, Brooklyn could sign Durant as a UFA whether Golden State played along or not. Given no leverage, Golden State was happy to explore a deal that got them better than nothing.

...

Turning to next summer, the potential Derrick White free agency scenario we're talking about is one where presumably his current team wants him to stay (different from Butler) and presumably the potential new team can't sign White as a UFA (different than Durant). At that point a sign-and-trade becomes a more challenging negotiation to pull off.

Because Boston's (presumed) desire to keep White points in the opposite direction of working something out fast to the satisfaction of White's agent and the other team(s).
 

lovegtm

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You may well be right and I'm overcomplicating this. (It's been known to happen; just ask my wife).

From a place of kindness, tho, I'd caution against assuming you know *why* a stranger on the internet is (from your perspective) overcomplicating this







Mmmmmm.... kinda

When Jimmy Butler wanted out of Philly in 2019 one key to the sign-and-trade negotiation was that Philly wanted him gone. He'd been clashing with Brett Brown and Ben Simmons, and the front office threw their lot in with Simmons and Tobias Harris. Is a sign-and-trade easier when the player's current team wants that guy gone? Sure. As you've said upthread, at that point the choice is between something or nothing. And the former looks better.

When Kevin Durant hit free agency in 2019 the Brooklyn Nets were sitting on >$30M of almost-max cap space and had little trouble moving a few small contracts to get all the way there. So, in effect, Brooklyn could sign Durant as a UFA whether Golden State played along or not. Given no leverage, Golden State was happy to explore a deal that got them better than nothing.

...

Turning to next summer, the potential Derrick White free agency scenario we're talking about is one where presumably his current team wants him to stay (different from Butler) and presumably the potential new team can't sign White as a UFA (different than Durant). At that point a sign-and-trade becomes a more challenging negotiation to pull off.

Because Boston's (presumed) desire to keep White points in the opposite direction of working something out fast to the satisfaction of White's agent and the other team(s).
I'm sorry for assigning motives to the overcomplication. I will withdraw that, and say that, for any number of possible reasons, you making the degree of difficulty of an S&T higher than it generally is, and that that materially impacts DWhite's free agent options.

Durant and Butler were the first two examples that came to mind. Off the top of my head, I cannot think of a single example in the last 20 years where a UFA wanted an S&T and wasn't able to get it because the original team blocked it. Probably there are some, but it's really, really really rare.
 

Eric Fernsten's Disco Mustache

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I will withdraw that
No worries


I cannot think of a single example in the last 20 years where a UFA wanted an S&T and wasn't able to get it because the original team blocked it
If we're talking about (1) a UFA who wants to go to a team that can sign him as a UFA, then I'd suspect you're 100% correct

This may be my own stupidity, but I thought we were exploring (2) how easily White could orchestrate a sign-and-trade to a team that *couldn't* sign him as a UFA, and so needed Boston's collaboration to pull this off.

The number of teams in each category is unknowable now, but if White were hitting free agency this summer group (1) would be only 5-6 teams. And group (2) the rest of the league, or >25 teams.
 
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pjheff

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DW doesn't seem to have the natural confidence that the other players at his level do. It's something that he has openly talked about.
I can see that if we’re talking about the playoffs in ‘22, but does it still hold true now?
 

lovegtm

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No worries




If we're talking about (1) a UFA who wants to go to a team that can sign him as a UFA, then I'd suspect you're 100% correct

This may be my own stupidity, but I thought we were exploring (2) how easily White could orchestrate a sign-and-trade to a team that *couldn't* sign him as a UFA, and so needed Boston's collaboration to pull this off.

The number of teams in each category is unknowable now, but if White were hitting free agency this summer group (1) would be only 5-6 teams. And group (2) the rest of the league, or >25 teams.
Yes, we were talking about teams that needed collaboration. I just can't think of any cases where even that was blocked.

Then there's the whole category of "teams that can credibly threaten to clear space, even if it hurts them somewhat", which opens things up further.

For these reasons, I don't think it makes analytical sense to restrict DWhite's market in 2025. If he wants to take the injury risk of not extending to get a huge payday and play for a good team, he can do it.
 

jmcc5400

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Yes, we were talking about teams that needed collaboration. I just can't think of any cases where even that was blocked.

Then there's the whole category of "teams that can credibly threaten to clear space, even if it hurts them somewhat", which opens things up further.

For these reasons, I don't think it makes analytical sense to restrict DWhite's market in 2025. If he wants to take the injury risk of not extending to get a huge payday and play for a good team, he can do it.
Wouldn't White be a perfect complement to Wemby? Culturally he already fits into the Spurs mold and I am sure he has a comfort level there. I think he's the type of guy who will take less than top dollar to stay in Boston because that's just his personality, but if there is one team that strikes me as being a "threat" to poach him, it's San Antonio.
 

wade boggs chicken dinner

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This may be my own stupidity, but I thought we were exploring (2) how easily White could orchestrate a sign-and-trade to a team that *couldn't* sign him as a UFA, and so needed Boston's collaboration to pull this off.
I can't think of an example where a team blocked a FA from going to the destination of his choice. Given a choice between leaving for nothing (going to a team with cap space) and getting something back in a S&T, it would be difficult to imagine a situation where a team would tell the player to just leave.

Plus if the acquiring team doesn't have the cap space, the team losing the player has lots of leverage to get something better than zero.
 

lovegtm

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Wouldn't White be a perfect complement to Wemby? Culturally he already fits into the Spurs mold and I am sure he has a comfort level there. I think he's the type of guy who will take less than top dollar to stay in Boston because that's just his personality, but if there is one team that strikes me as being a "threat" to poach him, it's San Antonio.
Wemby would be in year 3. Minny is already contending for a title with Ant in year 4, and Boston was with Tatum in year 3.

It's one great fit. There are plenty of others.
 

benhogan

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His Playoff 3-point shooting is money

2023: 45.5% - 50/110 in 20 games
2024: 50% - 28/56 in 6 games

For the millionth time, the ball needs to be in his hands more when they initiate the offense
 

lovegtm

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If being a top-10 player is about having all your jumpers go in while playing good D (hi, Twitter!), we should add Derrick to the "Tatum vs Ant" thread.

Seriously though, "40%+ on high-volume with all the other stuff he does" DWhite should be uncomfortably high on player ranking lists.
 

benhogan

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Preach. This drum needs to continue to be beat.
Everyone in the rotation can shoot, & only gets better when the bench enters.

Has there ever been an NBA team with a TOP 8 that hits 3s like this group?
Usually, a team will have one stiff (The Dubs had non 3-point shooters like ZaZa, Looney, Livingston, Bogut)

I'm drinking the Mazzulla ball kool-aid
 

BigSoxFan

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Apropos of this thread title, the idea that White is a “playoff alpha” is not getting a lot of support from the dude’s play tonight
My math may be a game or two off but I counted the Celtics to be 37-7 this year, including playoffs, when White scores 15 or more.

That’s basically a 69 win pace. So, just like tonight, when he’s not scoring….I get worried.
 

Eric Fernsten's Disco Mustache

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Sorry about that post, I was tired and frustrated and angry.

IIRC, when I put it up White had tried, twice, to take a mediocre defender off the dribble and not been able to get around him, and then had fumbled around for a bit with ball while help defenders complicated things, after which he (i) missed a midrange shot badly; and (ii) made a bad pass for a turnover. So, not what you'd want to see from someone who creates advantages that other people build on.

Either way, it's a bad idea to post when you're grumpy.
 

lovegtm

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Sorry about that post, I was tired and frustrated and angry.

IIRC, when I put it up White had tried, twice, to take a mediocre defender off the dribble and not been able to get around him, and then had fumbled around for a bit with ball while help defenders complicated things, after which he (i) missed a midrange shot badly; and (ii) made a bad pass for a turnover. So, not what you'd want to see from someone who creates advantages that other people build on.

Either way, it's a bad idea to post when you're grumpy.
Yeah, he looked bad trying to create advantages for himself last night, and then forced a lot of 3s. It's weird, because he's usually able to beat the Garlands of the world.
 

Bunt4aTriple

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Any news on White? He hit that three, grabbed his side and threw up the German three fingers, then went to the tunnel. I saw him grabbing at after he returned.
 

joe dokes

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Any news on White? He hit that three, grabbed his side and threw up the German three fingers, then went to the tunnel. I saw him grabbing at after he returned.
Based on the quick return, I actually thought throwing up was a possibility. (Or he dropped a deuce before swishing a trey.)
 

Ale Xander

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I hope they can resign him but I doubt they can afford all of the top 5 (plus maybe even Horford) at the same time. He’s the second Celtic is most like to see stay on the team (after Tatum) even though he’s probably like the 4th or 5th most important.
Need that cap to go up convincingly.

(thank you for the invite, @InstaFace)
 

DeJesus Built My Hotrod

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I hope they can resign him but I doubt they can afford all of the top 5 (plus maybe even Horford) at the same time. He’s the second Celtic is most like to see stay on the team (after Tatum) even though he’s probably like the 4th or 5th most important.
Need that cap to go up convincingly.

(thank you for the invite, @InstaFace)
I bet Brad Stevens pulls into parking spaces differently than you.
 

scottyno

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I hope they can resign him but I doubt they can afford all of the top 5 (plus maybe even Horford) at the same time. He’s the second Celtic is most like to see stay on the team (after Tatum) even though he’s probably like the 4th or 5th most important.
Need that cap to go up convincingly.

(thank you for the invite, @InstaFace)
Good thing nba doesn't have a hard cap
 

InstaFace

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Good thing nba doesn't have a hard cap
Well, no, but the tax multipliers do get quite punitive now. I think repeaters end up paying $5 for every $1 they're over after a certain threshold. In theory it's just a problem for Wyc and Pags; in practice, it's one that ends up affecting the roster of every front office that's tested the outer limits of the tax system.
 

scottyno

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Well, no, but the tax multipliers do get quite punitive now. I think repeaters end up paying $5 for every $1 they're over after a certain threshold. In theory it's just a problem for Wyc and Pags; in practice, it's one that ends up affecting the roster of every front office that's tested the outer limits of the tax system.
Weren't you arguing that they wouldn't be able to afford to keep jrue like days before they extended him? They haven't done anything to show they aren't committed to keeping this group of 5 together for this cycle of the next few years
 

InstaFace

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Weren't you arguing that they wouldn't be able to afford to keep jrue like days before they extended him?
I don't think so? Feel free to quote me if I've said it, though. Wouldn't be the first time I've been wrong if so.

Generally, though, I've believed Wyc when he's said he's willing to spend any amount of money to build and keep a championship team. He's said that repeatedly, in public, and emphasized the lack of a hard budget. And since they did the Jaylen supermax without any hesitation, I think at this point he deserves to be believed in that statement until he shows otherwise.
 

Euclis20

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Weren't you arguing that they wouldn't be able to afford to keep jrue like days before they extended him? They haven't done anything to show they aren't committed to keeping this group of 5 together for this cycle of the next few years
If we fast forward 14 months and haven't won the title yet, I have a hard time believing that ownership will spend a billion dollars to keep together a group that has both never gotten over the hump and whose best days are likely behind them just based on the age of some of the starting five (average age will be just over 30 for the 25/26 season). I don't think that necessarily means that White is the one to go, but I have a hard time imagining us running out a starting five of White/Holiday/Brown/Tatum/Porzingis in October 2025 unless we've won the title either next month or next year.
 

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I think we should all take with a grain of salt the idea that management and ownership has really clear plans that they're committed to for more than a few weeks or a few months into the future

Too much changes in the league, and in the lives of NBA owners, for that to work in practice. Wyc and Pags and Brad have probably talked in general terms about how much they think they'll be willing to spend in a year or two or three. But nobody knows what the TV deal is going to bring in, or what the team and the league will be like then. I suspect the front office is operating on some list of broad principles, and then tacking back and forth all over the place in response to current events.

So Jrue becomes available and you trade for him. Was it discussed at some point previously as a hypothetical? Almost surely. Was it consistent with the general direction they'd agreed on? Probably. Was it part of some detailed plan for how the last few years was going to go? I doubt such a thing exists, in a form we'd recognize.

I doubt there's a detailed plan for the next few years, either. There are too many unknowns. I suspect they have a bunch of operating principles, and then a bunch of scenarios for how they imagine acting on them, and then they're figuring out the rest as they go
 

lovegtm

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If we fast forward 14 months and haven't won the title yet, I have a hard time believing that ownership will spend a billion dollars to keep together a group that has both never gotten over the hump and whose best days are likely behind them just based on the age of some of the starting five (average age will be just over 30 for the 25/26 season). I don't think that necessarily means that White is the one to go, but I have a hard time imagining us running out a starting five of White/Holiday/Brown/Tatum/Porzingis in October 2025 unless we've won the title either next month or next year.
Wyc's already shown that he'll say to blow it up and reconfigure if the situation warrants, so yes.

They'll have the matching salaries and draft picks to change on the fly if they need to (this applies even if they win the title).

It's the NBA, so I expect the roster to look drastically different in 2026. Stuff always changes, and fast.
 

lexrageorge

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I think we should all take with a grain of salt the idea that management and ownership has really clear plans that they're committed to for more than a few weeks or a few months into the future

Too much changes in the league, and in the lives of NBA owners, for that to work in practice. Wyc and Pags and Brad have probably talked in general terms about how much they think they'll be willing to spend in a year or two or three. But nobody knows what the TV deal is going to bring in, or what the team and the league will be like then. I suspect the front office is operating on some list of broad principles, and then tacking back and forth all over the place in response to current events.

So Jrue becomes available and you trade for him. Was it discussed at some point previously as a hypothetical? Almost surely. Was it consistent with the general direction they'd agreed on? Probably. Was it part of some detailed plan for how the last few years was going to go? I doubt such a thing exists, in a form we'd recognize.

I doubt there's a detailed plan for the next few years, either. There are too many unknowns. I suspect they have a bunch of operating principles, and then a bunch of scenarios for how they imagine acting on them, and then they're figuring out the rest as they go
Agree, as there was no way Stevens and Wyc were sitting in a room in 2021 with a plan that said "trade for Jrue Holliday in 2023". Too many things happen to be able to plan that far ahead with any degree of precision.
 

slamminsammya

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The new TV deal is possibly several multiples of the old one (I have seen multiple sources saying 3x the current annual figure). While the salary cap can only increase max 10% annually, I would think substantially more TV revenue might soften the blow to the Celtics' cash flow if that is an issue.
 

lovegtm

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14,290
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The new TV deal is possibly several multiples of the old one (I have seen multiple sources saying 3x the current annual figure). While the salary cap can only increase max 10% annually, I would think substantially more TV revenue might soften the blow to the Celtics' cash flow if that is an issue.
At the very least, it will open up some creative financing deals that would make the cash outlays for a massive tax bill somewhat sustainable.
 

benhogan

Granite Truther
SoSH Member
Nov 2, 2007
22,219
Santa Monica
Weren't you arguing that they wouldn't be able to afford to keep jrue like days before they extended him? They haven't done anything to show they aren't committed to keeping this group of 5 together for this cycle of the next few years
FWIW we talked about a Jrue April extension around here since the day Brad made the trade 8 months ago. There was very little pushback. I can't recall a poster thinking ownership wasn't going to ante up (vs. Sox fans angry with ownership FA spending)

I guess there were a few who thought Jrue would want to maximize his earnings by going to UFA this summer.