Jrue Holiday's new contract: How does it impact the Celtics roster construction?

Cap connoisseur Keith Smith answers some of my burning questions following Jrue Holiday's contract extension.

The Boston Celtics have inked Jrue Holiday to a four-year $132 million contract extension. He will reportedly opt out of his player option for next season, slashing approximately $35 million off the Celtics' luxury tax. Overall, this is another All-Star piece of cap acrobatics by Brad Stevens and Mike Zarren.

Still, there’s no denying that the Celtics, as currently constructed, project to become a mouth-watering, mind-boggling, time-space-continuum-bending, Excel-sheet-breakingly expensive team in the coming years.

Jaylen Brown’s Supermax contract kicks in next season. Holiday’s new deal will now kick in. Jayson Tatum will eventually sign a Supermax contract. Derrick White is extension-eligible — which the Celtics will need to resolve sooner rather than later.

Luke Kornet and Xavier Tillman are both entering unrestricted free agency this summer. And Sam Hauser will be entering the final year of his deal next season.

There’s a lot to keep track of, and there are also a ton of caveats to consider, such as Boston owning White’s Bird Rights and the punitive second apron.

I’m no cap expert. I don’t claim to be. So, the best way for us to get a better grip on this subject is to reach out to someone in the know. We need to find an expert. Fortunately, my former colleague at CelticsBlog, and someone I consider to be a personal friend,

Keith Smith

of the

The Basketball Bulletin

newsletter (I highly recommend subscribing) is one of the best around.

Keith has graciously provided me with some of his time so that we can better grasp how Holiday’s contract extension could potentially impact the Celtics moving forward.

The discussion was laid out in Q&A format to make it easier to chunk my questions and the answers Keith provided. Let’s jump in.

Adam: Bobby Marks shared some numbers after the deal was announced. For the non-cap experts in the group, how does this deal save Boston money, and can they duck under the second apron in the summer or before the 2025 trade deadline?

**The above image is from Marks’s tweet after the deal had been announced. Click here to see his Tweet in full.**

Keith: Ducking under the apron this season for Boston, even with Holiday at about $30 million, is nearly impossible. And that's actually a good thing for Celtics fans because it means the team won't be getting broken up. If we include Oshae Brissett and Sam Hauser (they have a player and team option, respectively), and the team's first-round pick, Boston projects to be at about $192 million.

That's before filling the final couple of roster spots and before any kind of new deal for Luke Kornet, Xavier Tillman Sr. or Svi Mykhailiuk. That means being over the second apron is a reality, minus making a major move to shed some salary.

Adam: Holiday's new deal could see him earning ~$30 million at age 37. Some might view this as an overpay. Does this deal give the Celtics a potential trade chip on the back end of this contract? What I'm essentially asking is...Is this the sort of deal teams could look to hand out as they navigate the new CBA rules...So that they have a significant contract to match salaries in bigger trades or to turn one player into two or three?

Keith: One of the overlooked things about this deal is that it locks in Holiday for the Celtics, which is obviously good. It reduces the tax bill for next year, which is good for ownership. But it also gives Brad Stevens some tradable salary to work with down the line. Let's say we're in the 2026 offseason, and Boston has some depth issues. They can move Holiday, who will likely be making around $35 million that season, in a deal to replace some depth. Having some movable salary is going to be huge for teams dealing with the second apron.

Adam: With Holiday's contract secured, attention will turn to Derrick White who is extension eligible. Boston has White's bird rights...The question is, how much does Holiday's deal potentially impact Brad Stevens' ability to retain White as well? 

Keith: Retaining White is really a question for Stevens to work out with ownership. Nothing prevents Boston from signing White to whatever it will take to keep him...beyond massive salary plus tax implications. All these moves are being done with the immediate and the long-term in mind. But there's also a bit of "let tomorrow's problems be tomorrow's problems" at play here. Such is life when you're trying to win a title.

Adam: Tatum will need to sign a supermax deal eventually, too...Can the Celtics sustain all of these contracts long-term? After all, Brown's supermax kicks in next season...Factor in Holiday, Porzingis' extension, and potentially White...How long can this team stay together? 

Keith: The simple answer: For as long as they are competing for the title. Long playoff runs and potentially winning a championship will go a long way toward easing any concerns over paying a massive payroll bill. The more difficult answer involves hitting a decision point if the team falls short of contending for a title. At that point, paying this kind of money for a team that isn't getting it done is untenable.

Adam: The Celtics are committing a ton of money to the top of their rotation...Sam Hauser will be entering his final year next season...Can they afford to keep him around, too? There has to be an inflection point somewhere, right? 

Keith: To an extent, Hauser could end up a casualty. Something will eventually have to give, especially around the edges of the rotation. But if Boston can get Hauser locked up to an extension that pays him fairly but not exorbitantly, that's important. It's more likely that Hauser on a fair-value deal will stick than, say, Jaylen Brown or one of the guards. Moving off of ~$10 million in salary simply doesn't have the bang for the buck that moving $30 to $40 million would.

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Some thoughts on Holiday’s extension

The news of Holiday’s extension broke while I was asleep. That’s something I’ve become accustomed to. Covering the NBA, or even being an NBA fan, from this side of the pond has its quirks. I like to look at this with a glass-half-full mindset. Yes, I’m behind on the news cycle sometimes. But by the time everyone else wakes up, I’m all caught up, I’ve done my research, and I’m sharing opinions just like everybody else.

Speaking of opinions, here’s mine.

Holiday and White have proven themselves to be the best two-way backcourt in the NBA. Both are elite defenders, can run an offense, and can thrive without the ball in their hands.

Since joining the Celtics, White has been utilized in a multitude of ways. He’s operated as a release valve in the corners, where he’s converting his shots at a 43% clip, per Cleaning The Glass. He’s shone as an inverted screener and inverted dunker spot threat. And he cooked when switching onto bigger opponents on the defensive end.

There’s a reason the Celtics have used him as the “spy” in their 2-1-2 zone defense and why they’ve started out games cross-matching him onto bigger, stronger opponents. His versatility, processing speed, and selflessness have all been core factors in how he’s successfully embedded himself into what is clearly a championship roster.

I get that it’s easy to look at his impact metrics and see a slide this season. He’s averaging an 11-year low +1.8 in Estimated Plus/Minus.

However, you have to contextualize the talent around him. The role he’s playing and how he’s doing more to impact the game in ways that don’t always show up on the box score. As we’ve seen when players are out of the rotation, Holiday is still capable of sliding into a bigger role, similar to what we’ve seen from him in previous seasons.

That’s why Stevens has been wise to extend his contract. There aren’t many players who would be willing to take such a significant step back in role and production while gladly signing up for more of the same. When you have as much talent and depth as the Celtics do, everybody has to sacrifice — some more than others. Holiday has bought into that mindset. Some might view that as drinking the Kool-Aid. I view it as a veteran doing what needs to be done to put himself in a position to win another ring.

Holiday was once the missing piece to the Milwaukee Bucks’ championship aspirations. He could prove to be Boston’s missing piece, too. Either way, trying him down for another four years on a contract that gives the front office some flexibility in the trade market on the back end of the deal is a massive win for the Celtics.

I’m sure we will be diving deeper into Holiday’s impact on the roster in the near future. I’m also guessing there will be a film breakdown at some point (because, let’s face it, I can never help myself), and I’m hoping I get to write a contemplative piece after Banner 18 has been secured at the end of the season.

For now. I’m all in on keeping this championship window open as long as possible.

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