Jrue Holiday trade tips balance in East (again) with consequences far beyond Boston

By David Aldridge, Sam Amick, John Hollinger and Mike Vorkunov

Amick: At least the Bucks squeezed in their Welcome-to-Milwaukee rally for Damian Lillard on Saturday before the Eastern Conference ante was upped yet again.

The Boston Celtics would like the star player spotlight now, please. And with good reason.

By landing 33-year-old All-Star guard Jrue Holiday in a deal with Portland that was finalized on Sunday, when they sent point guard Malcolm Brogdon, big man Robert Williams and two first-round picks to the Trail Blazers, this Celtics organization that came just two wins away from the title in 2022 pulled off the kind of “hold our beer” countermove that many will argue makes them the new favorites in the East. When it comes to being bold and going for broke (literally and figuratively) during this time when the NBA’s new rules were supposed to discourage this kind of roster craziness, this has been an impressive few days for Bucks general manager Jon Horst and the Celtics’ Brad Stevens.

Before we analyze this latest megadeal from every angle, this much has to be said: Poor Joel Embiid. All summer long, the reigning MVP stayed patient during the contentious James Harden saga that still has no resolution in Philadelphia. He saw Bradley Beal get the kind of hoops help he’s always dreamed of by going from Washington to Phoenix in June, with Lillard following suit when he was dealt to the Giannis Antetokounmpo-led Bucks group that is absolutely loaded. But as Embiid hinted on social media in the immediate aftermath of the Holiday deal, this one might have hurt the most.

Cue the sad trombones…

Holiday, who was drafted by the Sixers out of UCLA in 2009 and spent his first four seasons in the City of Brotherly Love, would have fit in beautifully with these Sixers. The veteran presence. The championship credentials. The two-way play that remains among the best in the Association. Alas, it was not to be.

The Sixers were among the many teams known to be pursuing Holiday in recent days, with the Clippers also seen by rival teams as a serious suitor. But the Celtics got the deal done, and I can’t help but wonder what it might mean for the next phase of the Harden experience that’s to come. As you all know, the rumblings about Embiid eventually asking out have been growing louder for quite some time now, and nothing that transpired in recent days did much to lower the decibel level on that front. Also, by the way, the Sixers have media day in Philly on Monday and will be in Fort Collins, Colo., for training camp starting Tuesday. After Harden vowed in mid-August to never be a part of any organization that includes Sixers executive Daryl Morey, it’s unclear if he will take part in camp.

So before we talk about all the ways the Celtics got even more dangerous, how do you see the ripple effect on the Philly situation here?


Jrue Holiday trade grades: Boston rotation takes a hit; will it be worth it?

Aldridge: I’m here in Philly! At the Commanders-Eagles game Sunday. I’ll be at Sixers media day Monday. Should be … fun.

Hollinger: It feels like it creates more urgency for Philadelphia (or Miami, for that matter) to do something, but … what, exactly? Clearly there is now a Red Sea-level separation between the top two contenders in the East and everyone else, an amazing thing to say since neither Boston nor Milwaukee won the conference last season. But Miami lost key pieces and the all-in move for Lillard and/or Holiday evaded them, and Philly has yet to come anywhere close to finding a suitable Harden trade after losing to Boston in seven games this past spring.

Certainly Embiid has to be looking around and at least, you know, asking some questions. The Sixers are still set up to have max cap room a year from now and could potentially use it to bring in Embiid’s fellow Cameroonian Pascal Siakam, but is that really a move that gets them over the top in this East? And what about the coming season? They can’t just punt a year of Embiid’s prime on a meh roster that maybe wins one playoff series, right?

As bad as this all went for Miami, you could argue it may be even worse for Philadelphia, which still has no Harden resolution, has seen the market remove two All-Star Harden replacements from the potential acquisitions list and is having to navigate the same rumblings of superstar impatience that both created Lillard’s trade demand and the Bucks’ subsequent move to acquire him. The Sixers will try to wait this out, I guess, as they did with Ben Simmons, but I don’t yet see a great exit strategy for Philly if Harden either refuses to play or (perhaps worse) shows up but mails it in.

Amick: You do wonder now if the Clippers might finally feel compelled to put more on the table for Harden. Despite his well-chronicled desire to land there, the Clippers were clearly serious about going with Holiday instead. But maybe their increased level of desperation here is the Sixers’ silver lining.

For all of our focus on Philly and Miami, there’s been a shift in the West power structure too with the Beal-Suns move and even the Chris Paul addition to the Warriors. The Clippers, who are four years into this Kawhi Leonard-Paul George era and have very little to show for it, haven’t been able to keep up just yet.

DA, you deemed the Lillard move a “Holy (bleep)!” moment a few days ago. How did this one hit you?

Aldridge: Can I just say how happy I am? Not because I’m a Celtics fan or a Bucks fan or a Suns fan. I’m an NBA fan. And the virtual ink on the new CBA isn’t yet dry, but here are multiple teams that are just blowing through the first and/or second luxury-tax aprons, whether immediately or in the near future, in pursuit of a championship. I know, “Ringz Culture” is bad now. It’s all about the journey and the joy in playing, etc. And there’s some truth in that. But we go through a six-month regular season and two months of playoffs to find out who wins. This isn’t a voluntary sports league, right?

I was concerned after the Warriors got Kevin Durant in 2016, because so many teams’ decision-makers seemed so resigned to Golden State dominating that they didn’t seem very enthusiastic about challenging them. Only Morey and the Rockets dug in and gave it a shot. And, if you go back and look at that Houston-Dubs West finals in 2018, sometimes you’re amazed that the Rockets didn’t win it. Houston missed 27 straight 3-pointers in Game 7 and still could have pulled it out.

This summer is the antithesis of that 2016 offseason. First, the Suns quickly agreed to take on the remaining three years of guaranteed money — $150.6 million — of Beal’s contract, along with the likely $57.1 million Beal will get in his option year of 2026-27. That was on top of the outlay for the last three years ($153.5 million) of KD’s extension, along with another $6 million in incentives, and the $222.6 million extension for Devin Booker that kicks in after this upcoming season. Yes, Phoenix gets some relief down the road from trading Deandre Ayton to Portland for Jusuf Nurkić, but Mat Ishbia’s going to be paying more tax than Enron (whoops, too soon?) for a good long while.

Then, Milwaukee went all-in on Lillard, knowing that if the deal achieves its primary goal of getting Antetokounmpo to sign a rest-of-my-prime extension next summer, the tax implications in three years, when Lillard is making $63 million(!!), are staggering. Now, there’s Boston, which just gave Jaylen Brown a $300 million extension this summer, will have to give even more to Jayson Tatum within the next couple of years, gave Kristaps Porziņģis a two-year, $60 million extension and will now be on the clock to give Holiday a new deal next year.



As Celtics trade for Jrue Holiday, Malcolm Brogdon saga comes to an end

Vorkunov: It’s so true. If there was any concern the new CBA and its avatar of destruction, the second apron, were going to lead to some mass de-escalation, this offseason has shown just the opposite. NBA contenders are leaning into the risk. It’s really a beautiful thing to see.

Whatever concerns management might have about paying increasing luxury-tax multipliers or frozen picks kind of get muted when Antetokounmpo lays down the gauntlet as he did. Then that has a tack-on effect of pushing other teams in the East further in. I’m sure the Bucks didn’t like to see Holiday head right back to a team it might meet in the Eastern Conference finals next spring, but the Celtics surely had to feel some pressure to make another move to keep up. As all-in as they were before, it gets diluted if it no longer makes you as competitive against your best competition.

Hollinger: I think part of the reason, ironically, is the new CBA. If you’re a tax team and you want to make an all-in trade, you had  do it right now — before future picks get put in jail, starting in 2025, and before the rules against aggregating multiple salaries come into play next summer. Additionally, the trade rules almost incentivize these teams to have at least one whale salary, because you can aggregate down but not up. In other words, trading Lillard’s monstrous salary in two years for two smaller ones is still possible if you’re the Bucks, but the same trade won’t be allowed in the opposite direction.

That said, I think DA hit on the bigger underlying reason that so many teams are pushing chips in right now: the perception that it’s wide open, and thus that a “one piece away” type move is even possible. When the KD-era Warriors were roaming the Earth, that was a much more difficult proposition for a front office to talk itself (and ownership) into.

Finally, kudos to these teams —Milwaukee, Phoenix and Boston — that have been willing to spend themselves deep into the tax to go for it. Assuming Holiday extends his contract with the Celtics, all three are going to be very pricey rosters two or three years down the line, and the tax penalties under this new CBA are even harsher. These aren’t New York/L.A. situations when they can offset the tax because their home arena prints money; they’re knowingly taking a hit in the hope that a flag flies forever.

Let’s talk about the Celtics in particular, though, because this was an absolutely brilliant offseason for them. In sum, they turned Marcus Smart, Malcolm Brogdon and Robert Williams into Porziņģis and Holiday.

And it all stemmed from the willingness at first to take a half-step back and deal Smart to Memphis, which I’ve been led to believe was already in the works when the Porziņģis trade came up. One of the picks from that Grizzlies trade went with Boston’s own 2029 first to acquire both Holiday and Porziņģis. The Celtics got better at both point guard and center, and they already were an elite team.

(The Celtics also got the 25th pick from Memphis in the trade, sent the 35th pick to Washington, then traded down four times on draft night and got four future seconds to end up at No. 38 and take the player they were likely going to take anyway in Jordan Walsh. Shrewd, shrewd stuff.)

This does create some problems with their depth. Payton Pritchard has to step up into a rotation spot, Porziņģis has to stay healthy and 37-year-old Al Horford has to hold off Father Time for another year. The frontcourt depth in particular looks thin minus Williams and much less switchable in big moments. (The Warriors carved them up in the 2022 Finals any time Williams was off the floor, for instance.) Another steady wing would help too, and one would imagine they’re on the phone with the just-bought-out Reggie Bullock as we speak. Boston still also has its 2024 first to trade, among other picks, and could use that and aggregate several small salaries to get a quality frontcourt player, although it would make the Celtics even more expensive.

Is Boston too hollowed out now, or does it not really matter because the starters are so good?

Amick: I agree with everything you said there, John, but I do also wonder if this frontcourt path will ultimately pay off. A drop-off from Horford wouldn’t shock anyone, and Porziņģis’ health history is still the kind of thing where you’re always waiting for the other shoe to drop. This is still a move you have to make, but losing Williams, as you said, it’s hardly nothing.

Vorkunov: I’m really interested in how Boston has changed its team over the last year, not just with its roster. I thought maybe Boston was tilting a little too much toward offense and away from that voracious defense that got it to the Finals, especially in trading away Smart and adding Porziņģis. But in acquiring Holiday, the Celtics get a great defender again and another ballhandler and shooter who should benefit them on both sides of the court.

And let’s not get past the irony — if this happens — of seeing Holiday guarding Lillard in the Eastern Conference finals. You could not ask for a more obvious referendum on the Lillard/Bucks trade than that.

231010 Holiday Lillard scaled e1696214284616

Jrue Holiday and Damian Lillard meeting in the postseason for their respective new teams would be intriguing. (Jaime Valdez / USA Today)

Aldridge: I have to think, as John mentioned, that the C’s will be all-in on Bullock, who’s not looking to make all the money in the world, just to be on a good team that has a chance to compete at a high level. We all agree that fits Boston, right? Bullock and the Spurs had an amicable divorce; the Dame/Holiday machinations league-wide made a deal for the veteran marksman all but impossible this week, and no one wanted to wait any longer. But if they can’t get Bullock signed once he clears waivers Tuesday … I mean, a guy like Delon Wright, someone whose advanced defensive numbers are crazy good, is at least theoretically possible via trade. If Boston was willing to attach one or two of its remaining surplus picks in a potential deal, I can’t imagine Washington would reject it out of hand.

Hollinger: Is anyone else surprised this is the deal that Portland landed on? The draft picks aren’t likely to be as valuable as, say, two unprotected firsts from the Clippers or Heat. The Golden State pick likely ends up in the 20s, and the Celtics will probably still be good in 2029 with Tatum and Brown.

Is that an indication that rival teams weren’t ready to go quite so far in pursuit of Holiday? Or is there another angle here I’m missing? It seems like the Blazers valued getting Williams, who plays the same position as Ayton (whispers: and might actually be better) and is on a great contract that has three years left to run, so maybe that’s part of it. Brogdon presumably will move again, but I doubt he’s bringing back more than a dead contract and a couple seconds.

Aldridge: It feels a touch light, John, I agree. I’m guessing, though, that Portland didn’t want to haggle well into camp on maximizing a return for Holiday. Plus, Harden’s still out there, and there may wind up being multiple teams involved in that; they may have told Joe Cronin they’re keeping their powder dry until Philly makes a call on the Beard — whether or not they’re involved in the deal as a facilitator. OTOH, as elite as Holiday is defensively, he is 33, and he is the living definition of streaky offensively, and he is going to get one more massive payday. Would teams on the periphery of “contention” — good, solid playoff teams, but not great ones — be willing to anchor themselves to a nine-figure deal for him going forward? Just positing.

Vorkunov: To DA’s point, I wonder if this might be a real effect of the new CBA, that the guys who are very good but still sub-elite and also expensive or about to be very expensive are just going to get a smaller return on the trade market because of how punitive it becomes for the acquiring team. Holiday will make $36 million-plus and then potentially more if he opts out next summer when he’s 34. Maybe teams are willing to go big on a top-15 guy but will be a little more hesitant on players who don’t reach that level.

(Top photo of Jrue Holiday: Dustin Bradford / Getty Images)

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