Contract Conundrum: Do We Sign Jrue, Derrick, Sam? For How Much?

Auger34

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I don’t get this. The previous two years, his usage was 12th and 15th in the league, and he averaged 25 a game on a 57.8% TS. This year his TS is 57.4%.

He’s absolutely capable of going off when he’s hot, but leading the league in scoring, which is like 33+ a game? His game isn’t really equipped to deal with consistently being the focal point of defenses. He’s league average with efficiency while being in the perfect situation.
Honestly, I don't think Jaylen could lead the league in scoring. His 3 ball isn't good enough.

But your last two sentences don't really have anything to do with the discussion and probably lead to the confusion. The OP didn't say he'd lead the league in scoring, improve his efficiency and go on a deep playoff run (I bring up the deep playoff run because I don't think being the focal point of defenses in the regular season is the same as being a top 2 option in the playoffs). And if he's trying to lead the league in scoring, this really isn't the perfect situation. Too many mouths to feed (just like this isn't the perfect situation for Tatum to win MVP or get himself a scoring title)
 

RorschachsMask

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Honestly, I don't think Jaylen could lead the league in scoring. His 3 ball isn't good enough.

But your last two sentences don't really have anything to do with the discussion and probably lead to the confusion. The OP didn't say he'd lead the league in scoring, improve his efficiency and go on a deep playoff run (I bring up the deep playoff run because I don't think being the focal point of defenses in the regular season is the same as being a top 2 option in the playoffs). And if he's trying to lead the league in scoring, this really isn't the perfect situation. Too many mouths to feed (just like this isn't the perfect situation for Tatum to win MVP or get himself a scoring title)
Unless it’s one of the 3ish worst teams in the league, I don’t think any team would give a guy the green light to score 32-34 in today’s game if it’s on something like a 55-56% TS.

I also don’t think current Jaylen would force it enough to average that much, even if on a meh team. He’s figured out that consistently involving others makes the team better, and he’s started trusting that he will get the ball back if he moves it.
 

ALiveH

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I think that would be the plan. There is some belief that the groundwork of an extension was laid at the time of the trade. Barring catastrophe, my expectation would be that they keep this core together through the Porzingis extension and then reassess.
Yeah, I agree - keep the core together as long as possible, but once the cost starts to become prohibitive, Jrue seems like the one that is the most duplicative of other skills, oldest, worst player of the starting 5. And at his age, as a smallish guard, his production can drop off a cliff at any time. Lots of reasons to move on from him, even if the return isn't that much.
 

wade boggs chicken dinner

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Yeah, I agree - keep the core together as long as possible, but once the cost starts to become prohibitive, Jrue seems like the one that is the most duplicative of other skills, oldest, worst player of the starting 5. And at his age, as a smallish guard, his production can drop off a cliff at any time. Lots of reasons to move on from him, even if the return isn't that much.
Man, Jrue is the "worst player" and a "smallish guard" - he's had to sacrifice his reputation as well as his game this year. :)

By all accounts, Jrue is the leader of the defense and when they play the 2-1-2, he basically gets to do whatever he wants. That might be hard to replace.

However, as I posted upthread, it makes the most sense to me that if BOS needs to cut payroll, they'll shop Jrue around first. Hopefully, they get him at least one title before that happens. I'm excited to see Jrue in the playoffs - I definitely think he's got another gear, particularly defensively.
 

lovegtm

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Yeah, I agree - keep the core together as long as possible, but once the cost starts to become prohibitive, Jrue seems like the one that is the most duplicative of other skills, oldest, worst player of the starting 5. And at his age, as a smallish guard, his production can drop off a cliff at any time. Lots of reasons to move on from him, even if the return isn't that much.
When people say "small-ish guard", they almost always mean a 6-1 scoring guard who relies on quickness to score. Jrue is the opposite of that in a number of ways.

Brad acquired Jrue in order to extend him, and nothing Jrue has shown this year would have changed that plan. He's been great, and also looks like he's pacing himself, as wade boggs noted.
 

128

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When people say "small-ish guard", they almost always mean a 6-1 scoring guard who relies on quickness to score. Jrue is the opposite of that in a number of ways.

Brad acquired Jrue in order to extend him, and nothing Jrue has shown this year would have changed that plan. He's been great, and also looks like he's pacing himself, as wade boggs noted.
Yeah, we can enjoy an elite player for a full season before plotting to move him?
 

lovegtm

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Iguodala is a pretty good comp for Jrue. Let's hope it has the same effect!
You can use Iggy generally as the comp for anyone who can guard across most/all positions, is a good passer, and can do some things offensively. Jrue is smaller and so can't guard up quite as high, but he's a much much better shooter, and he scales that up further by relocating well around the court.
 

ALiveH

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Of course it makes sense to extend Jrue b/c the contract slot has value in a trade and when over the cap can't spend that money on a free agent.

I guess Jrue is really an average size guard, not smallish. Nevertheless, at 34 next year, he's in similar boat as four years older Al Horford (bigs age better than smalls) that he could drop off any year.

In addition to being the only starter well past his prime, my read is that out of the starters he's clearly the worst player (which is not a knock - he's still a great player) - each of the other four received at least some all-star consideration this year.
 

ALiveH

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If Iggy is the comp, he had about two good seasons left in him at Jrue's current age before he notably declined. And, that was with much less wear and tear (he was playing much fewer mpg than Jrue), and he's slightly bigger (bigger players tend to age better than smaller players).

You can use Iggy generally as the comp for anyone who can guard across most/all positions, is a good passer, and can do some things offensively. Jrue is smaller and so can't guard up quite as high, but he's a much much better shooter, and he scales that up further by relocating well around the court.
 

HomeRunBaker

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Of course it makes sense to extend Jrue b/c the contract slot has value in a trade and when over the cap can't spend that money on a free agent.

I guess Jrue is really an average size guard, not smallish. Nevertheless, at 34 next year, he's in similar boat as four years older Al Horford (bigs age better than smalls) that he could drop off any year.

In addition to being the only starter well past his prime, my read is that out of the starters he's clearly the worst player (which is not a knock - he's still a great player) - each of the other four received at least some all-star consideration this year.
I talk about a players value differing from one team to the next based on their role and there may be no greater example than Jrue. Really disagree with “well past his prime” when you can make the argument that he is coming off the two best seasons of his career.” Stats lie without context.

His first season in Boston kinda reminds me of Ray Allen’s in that when you aren’t as involved in the offense as you were previously it doesn’t mean that you are in decline in their cases….it is that your numbers and opportunities are simply a function of your diminished role in that teams offense from what you’re accustomed to being. He’s like inverse Jalen Brunson where they say in NY coffee shops wow look at how he miraculously improved over the 4-month summer….when he was the same player last year in Dallas in games when he had similar opportunity (without Doncic in the lineup).
 
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TripleOT

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ABC showed a graphic in the Knicks game of Jrue’s record the past few years when he plays. I added when he doesn’t play.

Plays Sits
2024 41-11 4-1
2023 50-17. 8-7
2022 47-20. 4-11
2021 41-16. 5-10

His winning percentage, the last four seasons, when he plays equates to a 60 wins season.
His team‘s winning percentage the last four season was when he does not play equates to a 33 win season.

To me, not re-signing Jrue is insanity. If he signs for four more seasons, and is only a decent player in year three, it still will be worth it. He is the ultimate team player, and his game is so well rounded that he can take any role that is needed.

Of course, I’m not writing the checks, but I would spend on the starters, and fill in the rest of the spots with minvets and rookie deal guys. Jrue and White is the dream backcourt to complement the Jays, and KP is the perfect center. Especially if Boston wins this season, ring chasers will line up for spots at the back of the rotation the next few years if Boston can’t afford AL, PP, and Hauser.
 

Imbricus

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ABC showed a graphic in the Knicks game of Jrue’s record the past few years when he plays. I added when he doesn’t play.

Plays Sits
2024 41-11 4-1
2023 50-17. 8-7
2022 47-20. 4-11
2021 41-16. 5-10
It's interesting the one year that there isn't a big split is this year (2024), but I think that's mainly a function of the Celtics just being insanely deep. So whether Jrue is on the court or not, they win anyway. Nice problem to have!

Sign me up (so to speak) for keeping Jrue. He's such a great complementary, selfless player. The three-point shooting has gone from pedestrian to elite, presumably as he's getting better looks at the basket from better spots.

I have noticed that quick guards tend to get past him, but he also seems to be able to dial up his defense to another level, and I think that's what we'll see come playoff time. My concern with Jrue is mainly over the money: I think we've got to be able to extend him at around $30 million per, or less, and not $35-$40. But I assume Brad has worked out those numbers with his agent.
 

benhogan

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I'm guessing Jrue will extend in April for ~ 3yrs/$90MM.

Adam Taylor weighed in on Jrue contract thoughts in a mailbag:

What sort of contract do you see Jrue Holiday receiving for 2024 and beyond?

Wow, a tough one right off the bat! Let’s start by looking at Holiday’s current deal. He has a player option for next season worth $37.3 million. Next season, he will be turning 34.

Earlier this week, The Athletic’s Shams Charania reported that Holiday is expected to be part of Team USA’s 12-man roster for the 2024 Olympics in Paris. MassLive Brian Robb believes his addition to the national team could expedite contract discussions between Holiday and the Boston Celtics front office.


"Holiday’s commitment to Team USA could be viewed as a sign that he feels like his long-term future will be settled well before Team USA begins training camp in late June," Robb wrote. "It would be a somewhat risky scenario for a veteran player coming off a deep playoff run to suit up at camp without having their future settled by that point with NBA free agency not set to begin until June 30th."
Let me preface this by saying that I’m not a cap guy. Still, I’ll give it a shot.

My take: The Celtics wait until Holiday is extension eligible, which is sometime in early April. A four-year deal with the final year being a player option makes sense. Given his age, the Celtics would likely look to reduce his salary but could reward him for sticking around. Something like a four for $72 million is a potential avenue.

That would provide Holiday with some additional security in the final stage of his career. An annual salary of $18 million would be a valuable trade chip in the current market, giving Boston some optionality on the back end of his contract if they decide to pivot toward a younger rotation in year three or four of the deal.

Holiday has discussed his desire to remain with the Celtics beyond his current contract.

“I’d like to be here,” Holiday said. “I feel like I’m getting more and more comfortable, loving the guys, loving the organization and loving the city.”

Boston is a second-apron team. They have a supermax contract negotiation on the horizon with Jayson Tatum. The ownership group will undoubtedly be willing to pay the tax for a contending roster. However, there has to be a line. That’s why $18 million per year makes sense to me. It’s (hopefully) enough to keep Holiday on the team and allow flexibility in the future.

If Brad Stevens can get Holiday to agree to a lower salary, perhaps in the $10-$15 million per year range, that would be a huge win. After all, he’s turning 34 next season. There will undoubtedly be a decline toward the back end of that contract. The key is making Holiday feel valued for the impact he’s made this season and will likely have in the coming years while also projecting age-related decline and limitations in the final year or two of the contract.
 

InstaFace

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Yeah @AdamTaylorNBA I just can't see Holiday taking a ~50% paycut in a rising-cap environment with him showing no signs of decline... there are too many teams out there who'd be happy to give him at least $25 possibly $30 the day that free agency opens and he can decline his option. Every marginal dollar we pay him is ~$4 out of Wyc's pocket, but other than extending him (or I guess a sign-and-trade), we have no real way under the cap to replace his talent level as a starter. I think he has a lot of leverage, and if they already have a handshake deal in place, it's probably for at least $25 and I would join the consensus here in expecting a $30 AAV. If Brad can get him to extend for less than that, add one more tale to his legend, I guess. But it's one thing to say "players like you tend to decline in their mid 30s, so I hope we can agree on $X", it's quite another to say "you, Jrue Holiday, who are performing more or less at the same level as the last 5 years, ought to be paid less now simply because you've aged a bit" and get him to agree. I can see him agreeing to a slight haircut in exchange for contract certainty, but not for anywhere near $18M, nevermind $10-15.
 

DavidTai

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In some ways, though, I can see him thinking "I don't want to move all over again". Having a large contract at the period he declines is gonna get him moved for a younger player who fits that slot better. If, on the other hand, he did like 30 million each for the first two years and dropped it after that, would he still be as desirable as a movable contract?
 

wade boggs chicken dinner

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Yeah @AdamTaylorNBA I just can't see Holiday taking a ~50% paycut in a rising-cap environment with him showing no signs of decline... there are too many teams out there who'd be happy to give him at least $25 possibly $30 the day that free agency opens and he can decline his option. Every marginal dollar we pay him is ~$4 out of Wyc's pocket, but other than extending him (or I guess a sign-and-trade), we have no real way under the cap to replace his talent level as a starter. I think he has a lot of leverage, and if they already have a handshake deal in place, it's probably for at least $25 and I would join the consensus here in expecting a $30 AAV. If Brad can get him to extend for less than that, add one more tale to his legend, I guess. But it's one thing to say "players like you tend to decline in their mid 30s, so I hope we can agree on $X", it's quite another to say "you, Jrue Holiday, who are performing more or less at the same level as the last 5 years, ought to be paid less now simply because you've aged a bit" and get him to agree. I can see him agreeing to a slight haircut in exchange for contract certainty, but not for anywhere near $18M, nevermind $10-15.
Yeah, so long as his contract is reasonable compared to the market, the Cs will sign him and worry about luxury tax later as they can always break up his contract into smaller pieces. I got to think the Cs would be happy to do 4/$120M but Jrue could likely get a lot more than that on the open market (even if his chance of winning goes down.)

In some ways, though, I can see him thinking "I don't want to move all over again". Having a large contract at the period he declines is gonna get him moved for a younger player who fits that slot better. If, on the other hand, he did like 30 million each for the first two years and dropped it after that, would he still be as desirable as a movable contract?
I think Jrue and his agent are smart enough to know that in today's NBA, most contracts no matter the size are movable. The only way he can stop himself from being moved is getting a no-trade clause, which the NBA doesn't give out very often (see Bradley Beal).

Still taking a discount and adding a no-trade clause in this case could be a win for everyone - particularly us as fans. Watching Jrue day-in and day-out (particularly on defense) has been a joy. His footwork is so good.
 

benhogan

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In some ways, though, I can see him thinking "I don't want to move all over again". Having a large contract at the period he declines is gonna get him moved for a younger player who fits that slot better. If, on the other hand, he did like 30 million each for the first two years and dropped it after that, would he still be as desirable as a movable contract?
Jrue was an All-Star last year and is being mentioned as one of the TOP 12 American NBA players (via Olympic team) this year.

I suspect Jrue sacrificing pointZ for the greater good of the team is the only sacrifice he'll be expected to make. Again, I expect Zaren/Brad already worked out the extension amount with Glushon/JH before trading 2 Firsts/Brogdon/TL.

They extended KP at $30MM/yr & would expect similar money for Jrue (and White this summer).

Jrue has developed into one of the better 3&D wings in the NBA (he'll age well with that role)
 

Devizier

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I speculated that Jrue would get something like what Lowry got with the Heat, which cap adjusts to around 3/105.
 

Imbricus

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They extended KP at $30MM/yr & would expect similar money for Jrue (and White this summer).
Upthread, lovegtm said they can only extend White at 140% of his contract until 2025, when he becomes an UFA. So this summer a deal would have to get done at about $28 million if I'm not mistaken with my math. Don't know if White takes that. I can see him holding out for something in the low to mid 30s, because this is his best chance to get paid.

And I agree with the consensus: Jrue ain't taking less than $20 million. If Brad pulls that off, I'll certainly kneel at the shrine.
 

benhogan

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Upthread, lovegtm said they can only extend White at 140% of his contract until 2025, when he becomes an UFA. So this summer a deal would have to get done at about $28 million if I'm not mistaken with my math. Don't know if White takes that. I can see him holding out for something in the low to mid 30s, because this is his best chance to get paid.

And I agree with the consensus: Jrue ain't taking less than $20 million. If Brad pulls that off, I'll certainly kneel at the shrine.
Agreed. $28MM Year 1

It would scale up yearly so somewhere around $30MM++/yr on average over 3 seasons
 

wade boggs chicken dinner

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Upthread, lovegtm said they can only extend White at 140% of his contract until 2025, when he becomes an UFA. So this summer a deal would have to get done at about $28 million if I'm not mistaken with my math. Don't know if White takes that. I can see him holding out for something in the low to mid 30s, because this is his best chance to get paid.

And I agree with the consensus: Jrue ain't taking less than $20 million. If Brad pulls that off, I'll certainly kneel at the shrine.
White has already turned down the 3/$85M extension I'm sure. I'm not exactly sure what White could get if he signed an extension this summer but I would guess that it would be something like 4/$125.

If BOS can get him to sign that extension, they'd do in a heartbeat.