Actually, it turns out, the Boston Celtics won the Damian Lillard trade.
Sure, the Milwaukee Bucks can—and should—celebrate the arrival of Lillard, the best playmaker and pick-and-roll partner Giannis Antetokounmpo’s ever had. But now Jrue Holiday, who was sent from Milwaukee to Portland in the Lillard deal, is shipping up to Boston, and the balance of power in the Eastern Conference might have already shifted again.
Boston will reportedly send Malcolm Brogdon, Robert Williams III, and two future first-round picks—the Warriors’ 2024 top-four-protected selection and its own 2029 unprotected first—to Portland in exchange for Holiday. In the process, the Celtics accomplish three key tasks. First, they improve their own roster in a vacuum. Second, they add the one player in the entire NBA who is perhaps best suited to guard Lillard; remember how thoroughly Holiday’s Pelicans destroyed Lillard’s Trail Blazers in a 2018 playoff sweep. Third, they keep Holiday away from other Eastern Conference rivals—Miami? Philadelphia?—who could have so dearly used his valuable skill set.
It’s hard to overstate how fearsome the new Celtics rotation will be in a playoff setting, even if they consolidated two rotation players into one with this trade. After losing in the conference finals to the eighth-seeded Heat last spring, the Celtics have spent the offseason refining their rotation around the Jayson Tatum–Jaylen Brown core.
First, Boston sent longtime point guard Marcus Smart to Memphis in a shocking trade that brought back Kristaps Porzingis and the Warriors’ 2024 first-rounder. That deal sacrificed backcourt defense and playmaking for a higher ceiling in the frontcourt—yet now Holiday can not only fill Smart’s role, but improve upon his two-way play, while Porzingis’s rim protection allows the Celtics to weather Williams’s loss.
By dealing away Smart, the Celtics ran the risk of compromising the defensive identity that had elevated them to true championship contention over the past two seasons. Boston led the league in defensive rating in the 2021-22 season, when Smart won Defensive Player of the Year and the team reached the Finals, and ranked second last season. But even though Holiday doesn’t have a DPOY award of his own, he is just as stout a defender as Smart, if not better: Holiday is one of only three players, along with Draymond Green and Bam Adebayo, to be named to an All-Defensive team in each of the past three seasons.
Granted, Holiday is four years older than Smart, and in the longer term, he presents Boston with a tough decision when he becomes extension eligible later this season. (With Brown and Porzingis tied up in extensions already and Tatum on the verge of signing a supermax, the Celtics roster could grow especially expensive soon.) But the physical Smart suffered a noticeable defensive decline last season while Holiday enjoyed perhaps his best season at the age of 32.
And on the offensive end, Holiday should provide an upgrade over Smart as well. Although he’s prone to the same bouts of erratic shooting, Holiday’s game seems better fit for a secondary role, which is what Boston needs next to the higher-scoring Tatum, Brown, and Porzingis.
Holiday can help run the offense when Tatum sits, depending on how coach Joe Mazzulla chooses to stagger his top talents. And the newest Celtic is an underrated shooter who should thrive if defenses pay too much attention to Tatum and Brown. Over the past three seasons, Holiday made 39.5 percent of his 3-pointers in the regular season, placing him next to high-profile shooters like Kyrie Irving, Zach LaVine, and Buddy Hield on the league leaderboard.
The chief risk Boston assumes with this deal is an excessively top-heavy rotation. The team could run into depth issues over the course of the season, especially with regard to big men, where Porzingis and Al Horford are the only proven contributors. Porzingis is prone to injury, while Horford is 37 years old.
But the team’s top six rotation players offer such a remarkable blend of high-end talent and balance, with shooting, defensive tenacity, and positional versatility, that this trade is certainly worth the gamble. With Holiday and Derrick White in the backcourt, Tatum and Brown at the wings, and Porzingis and Horford in the middle, Boston boasts tremendous two-way potential and lineup flexibility against any potential playoff opponent. Even Milwaukee’s new-look starting lineup should struggle to score consistently against the Celtics’ mighty defense.
Just last season, the Nuggets demonstrated that an elite top six (their starting five plus Bruce Brown) can be enough to win a title with good health. The Celtics are attempting to repeat that same formula this season.
Meanwhile, the Trail Blazers’ side of the deal—really, the second branch of their Lillard transaction tree—is just as much of a slam dunk. They have now effectively turned Lillard, Nassir Little, and Jusuf Nurkic’s bloated contract into:
- Deandre Ayton
- Toumani Camara
- Three future first-round picks, two of them unprotected
- Two future pick swaps, both unprotected
And they can potentially flip Brogdon and/or Williams for more future draft assets. Brogdon is an obvious trade target for a contender in need of additional backcourt depth, even if the combo guard is often injured. The 25-year-old Williams presents a more complicated case because the Blazers could decide to keep him and dream about his potential as another ultra-athletic member of an ultra-athletic core—but they’re already doing the same with a center in Ayton, and Ayton-Williams lineups seem like nonstarters given both bigs’ lack of shooting.
In any event, the Trail Blazers certainly fetched more from Milwaukee and Boston in the past week than they would have from Miami (and another team, if they’d subsequently rerouted Tyler Herro as they did Holiday). It was a master class in patience—and in sneakily stoking their own arms race among Eastern Conference powers. Step one: Send Lillard to the Bucks for Holiday, thereby simultaneously creating a need for a top guard defender among Milwaukee’s rivals and acquiring that very top guard defender. Step two: Send Holiday to the Celtics. Step three: Profit.
Not since Haviland Tuf tricked the great houses in “A Beast for Norn” has someone so capably manipulated an arms race for their own gain. (And if you understood that obscure sci-fi reference to a George R.R. Martin story that isn’t in the Game of Thrones universe, The Ringer really is the right website for you.)
All summer, the biggest question in the NBA was where Lillard would play next. After Lillard was traded, the biggest question became where Portland would send Holiday. But now, with apologies to the 76ers’ James Harden drama and apparent Joel Embiid discontent, the new biggest question looks more toward the future: Can we fast-forward to the Bucks-Celtics conference finals and the Holiday-Lillard mini-battle now?