Fortunes change fast in the NBA. Three days ago, the Milwaukee Bucks were lauded (in this space and others) for upending the league with a blockbuster that vaulted them to the top of a vulnerable Eastern Conference. But then, on Sunday afternoon, in another shocking trade that should tweak most projection systems, the Boston Celtics acquired Jrue Holiday from the Portland Trail Blazers for Malcolm Brogdon, Robert Williams III, and two future first-round picks (Golden State’s top-four-protected 2024 selection and Boston’s unprotected 2029 pick).
In the aftermath of a disappointing conference finals loss and Milwaukee’s trade for Damian Lillard, the Celtics saw an opportunity to evolve a championship-ready roster that was already reshaped by June’s swap of Marcus Smart for Kristaps Porzingis, and they pounced.
It’s a hollow claim in early October, but Boston should now be considered the favorite to win it all. Some might argue this point, with the Nuggets, Suns, Warriors, and Bucks all worthy, but as of today, it’s so hard to find any meaningful holes on the Celtics roster relative to the competition.
Holiday is an ideal two-way combo guard who can shoot (he made 38.4, 41.1, and 39.2 percent of his 3s the past three seasons), run pick-and-rolls, engineer quality looks for himself and others, torment just about anyone who’s unfortunate enough to draw his defensive assignment, and accentuate Boston’s two All-NBA forwards, Jaylen Brown and Jayson Tatum, by assuming numerous tasks on both ends that they’ll no longer have to worry about. The organization’s dramatic shift toward size and offensive variation swung back toward the middle when a valuable player nobody thought would be available suddenly found himself up for grabs.
Holiday was an All-Star last season, averaging 19.3 points, 7.4 assists, and 5.1 rebounds per game. He finished 16th in estimated wins and sixth in DARKO. He also helped guide the Bucks to a title in 2021, both brazen and brilliant on the sport’s biggest stage. Holiday’s most frustrating tendencies (overly ambitious and antsy decision-making) shouldn’t infect the Celtics team, which doesn’t need to stretch his limitations—as the Bucks were forced to do when Khris Middleton was hurt in the 2022 playoffs. Holiday was inefficient in all three of his playoff runs with the Bucks, but his hasty shot selection in the last two can at least partially be attributed to critical injuries elsewhere on Milwaukee’s squad.
He’s a good fit anywhere. Knowing that, Boston’s determination was likely fueled by the fact that making this trade prevents the Heat, Sixers, Warriors, Clippers, or any other potential playoff foes from acquiring him and getting significantly better. On the Celtics, he’s perfect. They add a reliable ball handler who can do pretty much everything Smart and Brogdon could at an even higher level, be it running the show or pushing in transition. He creates turnovers and can match up in transition with just about anyone, easing the burden when Boston’s retreating after a made shot. The Bucks have had a great transition defense for years, and Holiday helps explain why.
Boston’s lineup possibilities are nightmare fuel. The Celtics will have a potential starting five that should be at the top of any conversation for most talented and potent in the league: Derrick White, Holiday, Brown, Tatum, and Porzingis will produce unstoppable offense crossed with more than enough athleticism, tenacity, rim protection, and versatility to shut opponents down.
Solutions to slow the revamped Celtics down are few and far between. They can bully you all over the court with the switch-everything lineups that have carried their defense for the past few years or big, brutish units that shut down the paint and force offenses to settle over and over again.
White and Holiday both cracked an All-Defensive Team in 2023. Brown and Tatum are above average to great on the ball. Al Horford can still shuffle his feet along the perimeter and absorb blows in the post. Porzingis is an effective drop defender who will look even better with Holiday and White pursuing the ball. The Celtics are about the same size that they were when the season ended, but with Williams gone, they can now essentially always have five-out units running spread pick-and-rolls with centers who can’t be left alone 25 feet away from the basket. There will be so much room to operate in a drive-and-kick scheme that now has several new crunch-time resources worth exploring.
Holiday can manufacture quality shots for himself, too, but he’s also damn good at capitalizing on the attention earned by others. That’s good news for the Celtics. According to Second Spectrum, Holiday generated 1.27 points per direct play as the ball handler in closeout situations last year. That was seventh best out of 202 players who logged at least 250 plays. (Porzingis finished eighth.)
Despite a turnover rate that’s a little high for a starting point guard—which he won’t really be with White and Tatum running the show—Holiday typically makes smart decisions off the bounce, forcing a rotation and finding an open man who’s either spotting up or cutting through the open paint.
He can hit contested jumpers late in a shot clock—he’s been one of the best pull-up shooters in basketball over the past couple of seasons—and made a career-best 69 percent at the rim last year, all in roomy lineups, albeit not as spacious as what Boston may create. But Holiday was also one of 12 players who ended last season with over 78 percent of all their shots being self-created, per Second Spectrum (minimum of 500 attempts). It’ll be a good sign if that rate drops and he reduces some of the unnecessarily tough looks that were on display last year:
Zooming out, the Celtics may encounter an interesting rotation-related debate in the playoffs should they match up against Joel Embiid, Giannis Antetokounmpo, or Nikola Jokic and need to beef up their front line. But if and when Boston gets there, a situation that motivates Joe Mazzulla to bring White off the bench and play two capable bigs at the same time should be seen as a luxury instead of an internal headache.
In the meantime, the Celtics have all sorts of lineup combinations to experiment with that are explosive, stout, and flexible, aided by a supporting cast that’s thin on paper but primed to contribute in complementary spots. Sam Hauser, Payton Pritchard, and Svi Mykhailiuk are all movement shooters who can knock down open looks while holding their own in lineups that surround them with elite individual defenders. Oshae Brissett, Jordan Walsh, and Dalano Banton can provide a necessary injection of energy, hustle, and length. Holiday makes sense next to all of them.
(Unlike several other teams that are built to win the championship, Boston still owns its first-round picks in 2024, 2025, 2026, and 2027. Assembling enough salary to create a package that can then be dealt to improve on what they already have won’t be easy, but the Celtics still have tradable assets to play with, now and after the season.)
Health is a question for the Celtics, though. Boston just traded two very good role players to Portland, and will be asking an injury-prone Porzingis and a 37-year-old Horford to hold things down in the frontcourt. That’s a tough pill to swallow. Two years ago, they looked invincible with Time Lord on defense. (During the 2022 Finals, they were plus-30 with him on the court and minus-54 when he sat. Both were a team high.) Last year, the Celtics finished first in defensive rebounding rate and were never more capable on the glass than when Williams played. And in the conference semifinals, Boston was on the brink of elimination before Mazzulla stuck Rob back in the starting five. As a lob threat and someone who could really simplify pick-and-rolls for Tatum, he had singular skills that are impossible to replicate. Williams spaced the floor vertically and threw down anything that was tossed near the backboard. Will Porzingis be happy assuming some of that dirty work, creating second-chance opportunities on tip outs and putbacks? (The loss of Grant Williams stings now, too, with more size going out the door. But he’s far from irreplaceable.)
Brogdon’s exit removes a key scorer and the reigning Sixth Man of the Year. While Mazzulla can make up for the functional loss by staggering Tatum’s, Brown’s, Holiday’s, and White’s minutes, it’s here where Pritchard matters. As Boston’s third guard off the bench, the 25-year-old will be asked to spark an offensive punch, invigorate the game’s tempo, run coherent action, and face more responsibilities and higher stakes than he’s ever seen before. (Despite Pritchard’s size, he’ll also need to help out on the boards.)
Losing Brogdon and Williams III is a gamble that can potentially create issues that didn’t previously exist. But adding an All-Star—who has already been the missing piece on a title team—is worth that price. Sometimes you have to surrender awesome pieces to get even better. It’s a brand-new experience for everyone involved; only five rotation players remain from the 2022 Finals. Only Brown and Tatum are left from the bubble. But Mazzulla and his staff (including Charles Lee, who spent three seasons with Holiday in Milwaukee) have months to analyze who and what is in front of them, deciphering roles, delineating responsibilities, shaping their rotation, and formalizing a style of play that maximizes all that talent.
Holiday’s arrival makes that task a lot less complicated than it might’ve otherwise been. For 10 straight years, his teams have outscored opponents when he’s on the court and been worse when he sat. Put simply, he’s now on a team that can use all the ways he’s masterful without necessarily being desperate for any of them. There will be times when he’s a fourth option and games when he won’t have to guard the opponent’s top scorer. That’s basketball splendor. It also punches Boston’s ceiling up several notches to a height it hasn’t been in 15 years.
There are reports of mutual interest in a long-term extension, but that’s far from guaranteed at this stage. Nothing can be legally signed until March. (Something to keep in mind on that front: Holiday’s agent, Jason Glushon, also represents Brown, Horford, and Smart.) Until then, all the focus will be on raising an 18th banner at the end of this season. It’s championship or bust. There’s a deluge of pressure, a ton of money invested—this trade pushed the Celtics over the second luxury tax apron—and, now, more than one important contributor operating on the wrong side of 30.
Still, Sunday’s trade made every other contender sweat. Boston might’ve already had the most formidable team before Brad Stevens decided to enhance his nucleus by tacking on another All-Star, the type of player who should never be traded.
The Bucks felt otherwise. Just a few days ago, they were celebrating their own transformation, a league-shaking bet on one of the most gifted point guards who’s ever lived. Now, it’d be fascinating to know what Bucks GM Jon Horst truly feels, knowing his actions ultimately reinforced an archrival and gave it a defensive menace who’s had success guarding his new star point guard in the past. The irony is torture.
Would Horst still make the same choice if he knew Holiday would end up in Boston? Maybe. We’ll never know. But the Celtics sure are thrilled he did.
