The Milwaukee Bucks sent the NBA fandom into a frenzy on Wednesday afternoon, trading Jrue Holiday, Grayson Allen, and future draft capital to acquire Damian Lillard from the Portland Trail Blazers. After months of Lillard banging the drum for a Miami Heat trade, he ends up with the team Miami eliminated from the postseason, poised for a productive partnership with two-time MVP Giannis Antetokounmpo.
The two sides also roped in the Phoenix Suns, who sent beleaguered center Deandre Ayton to the Blazers in exchange for a gaggle of role players.
The Bucks are huge winners here. There is undeniable risk in dealing for a 33-year-old Lillard with four years and over $200 million left on his contract. The risk is offset, however, when the centerpiece of the deal is 33-year-old Jrue Holiday. There is also the Giannis factor. He has spent all summer threatening to leave the Bucks at the first sign of trouble. Dame reinforces the Bucks' focus on winning now — and winning big.
Milwaukee will enter the season as favorites to win the East, and maybe even the whole darn thing. Lillard is coming off the best individual campaign of his career — 32.2 points and 7.3 assists on 64.5 TS% — and he's the ideal pairing skill-wise for Giannis. Dame stretches defenses thin with his deep range; Giannis breaks them down the middle with his bulldozing drives.
Again, it is essential to emphasize how good Damian Lillard is. Much was said about his age, injury history, and the size of his contract. But this is Damian Lillard, a generational offensive talent who now joins the best team of his career.
The Bucks fanbase should be reveling in the streets. These teams, however, will probably come to regret their reticence upon watching the first Lillard-Giannis pick-and-roll.
5. Why the 76ers will regret not trading for Damian Lillard
Could the Philadelphia 76ers beat the Bucks' offer? That's the most important question here, and the answer is yes. The combination of Ayton, a former No. 1 pick, and Holiday (who the Blazers can flip for more assets) is a striking package, but it's far from the best superstar trade package in recent history.
The Sixers' only path to matching or exceeding the Bucks' offer would have been the inclusion of Tyrese Maxey. It's fair to question the logic of such a trade from both sides — Maxey is the Sixers' only real shade of youth, and the Blazers have too many guards already — but Maxey is a 22-year-old with room to grow. He is a better individual asset than Holiday or Ayton, and he would fit the Blazers' timeline.
The buzz all summer from Philadelphia was that Maxey is off the table for Dame or any other player. It's hard to argue with the Sixers' desire to keep such a promising talent in-house, especially with the volatility of the roster's older core. There's no telling when Daryl Morey will have to pivot to a rebuild.
On the other hand, the goal has to be to maximize Joel Embiid's title window. The Sixers can't afford to hedge their bets, because it will only result in more second-round exits. Losing Maxey would have been a tough pill to swallow and the risk would have been significant, but it's Damian Lillard. His 3-point shooting and halfcourt playmaking, paired with Embiid's scoring prowess inside the arc, would have established Philadelphia as Eastern Conference favorites. It may even have been doable without involving James Harden, who could either return for one last season under Morey or deliver more quality contributors to Philadelphia as part of a separate trade.
4. Why the Pelicans will regret not trading for Damian Lillard
The New Orleans Pelicans have more future first-round picks than they know what to do with. Team president David Griffin has done a tremendous job of building out a deep and talented roster while also stockpiling draft picks. At some point, New Orleans will have to consolidate assets. It's hard to imagine a better opportunities than this.
Lillard is the ideal point guard for New Orleans' roster. His 3-point dynamism, combined with Zion Williamson's rim pressure, would force defenses into an unsolvable conundrum. Factor in Brandon Ingram as the secondary initiator and connective tissue, and the Pelicans would potentially field the best offense in the NBA.
It is understood that Lillard would have protested an outcome like this, but he has four years left on his contract and narry a no-trade clause in sight. His bargaining power was ultimately very limited, and the results would speak plainly on the court. New Orleans is running out of time to make the Zion era happen. It's time to get risky. The Bucks got Lillard for a bargain-bin price. This was a huge missed opportunity for the Pels, who have all the assets necessary to blow Milwaukee out of the water in a bidding war.
With CJ McCollum as the tradable salary filler, it's not hard to pick out an intriguing collection of players from New Orleans' supporting cast — Trey Murphy III, Herb Jones, Jose Alvarado, Larry Nance Jr. — to go along with a few picks to sweeten the pot. That trade probably works out better for Portland, and it lands the Pelicans firmly in the contenders circle. There is risk, of course, primarily tied to health, but it's impossible to win a championship without taking a few swings.
3. Why the Celtics will regret not trading for Damian Lillard
The Boston Celtics pretty much sealed themselves out of the Damian Lillard hunt when Jaylen Brown signed his historic five-year, $303.7 million extension. That made Brown trade ineligible for a year, but it also made him significantly less appealing. Portland would have ultimately had to bite the bullet on the same deal, but it's like a new car. Once you drive it off the lot, it loses its luster.
Still, Boston would have been wise to strike while the proverbial iron was hot. Lillard is roughly seven years older than Brown and there's value in continuity. Say what you will about the Celtics' locker room last season, but Brown has been through hellfire with Jayson Tatum. That group has gone to battle time and time again. There's a certain level of unshakable trust and camaraderie that comes with that.
Here's the plain and simple truth, though: Damian Lillard is significantly better than Jaylen Brown. That's true in a vacuum, and it's especially true for the Celtics. Boston's core weakness was a lack of reliable playmaking in the backcourt. Lillard can generate advantages and share the ball. Brown is a talented shot-maker, but he's a butterfingered ball-handler with little peripheral vision on drives to the cup. The fit with Tatum has always been strained; not because of the skills they share, but because of the skills they lack (Brown far more severely than Tatum, to be clear).
Lillard's ability to create from scratch, spread the wealth, and execute in clutch time — or should we say 'Dame Time' — would have set the Celtics apart from a crowded Eastern Conference. Instead, the Bucks are a head above now. Boston should have been making every effort to get Dame in-house, even after Brown's extension. That made it complicated, but not impossible. And the Celtics can't let complicated get in the way of them and Banner No. 18 right now.
2. Why the Raptors will regret not trading for Damian Lillard
For a fleeting minute, it felt like Damian Lillard was going to the Toronto Raptors. ESPN scribe Marc J. Spears dubbed Toronto the "frontrunner," and the entire NBA fandom felt the striking similarity to Masai Ujiri's last blockbuster trade as Raptors GM: the trade that brought Kawhi Leonard north from San Antonio.
It would appear the Raptors were ultimately unwilling to part with O.G. Anunoby, the only sensible centerpiece for a Toronto package. While the Raptors' ongoing commitment to the 26-year-old out of Indiana is admirable, let's keep it real: Anunoby isn't good enough for the "off-table" treatment in Damian Lillard trade talks. If the Raptors are at all serious about winning, trading Anunoby for Lillard is a no-brainer.
There's a strong argument to be made that Toronto should simply rebuild, rather than clinging so tightly to a flawed roster with little hope of legitimate title contention. Lillard is a top-shelf talent, but he's not Prime Kawhi. The Raptors would not be favorites — or even second or third-favorites — in the East post-trade.
Unfortunately, the Raptors have swerved away from a rebuild at every possible fork in the road. Ujiri has passed up golden opportunities to trade veterans such as Kyle Lowry or Fred VanVleet, only to watch them walk away in free agency. The guiding principle behind such mishaps was a desire to win. If that's how Ujiri is going to run his team, why balk at an opportunity to genuinely compete?
Lillard is the perfect solution to Toronto's ailments on paper. He's a volume shooter and a gifted halfcourt playmaker who would give new head coach Darko Rajaković a bedrock to build his system upon. Alas, the Raptors will now gaze up from NBA purgatory as the Bucks make another title run.
1. Why the Heat will regret not trading for Damian Lillard
In the end, it felt like the Blazers were determined to send Lillard somewhere other than Miami. The Heat didn't even get the chance to counter Milwaukee's final offer, which goes to show how far apart the two sides were. For Lillard's agency to even hint at Milwaukee as a desirable destination probably took a serious lack of traction on the Heat front.
Still... Miami had the chance to make their best possible offer — including Tyler Herro, Caleb Martin, and the full complement of young prospects and draft picks — but never did. The Heat are an old team with very little financial flexibility. Miami is always a star destination, and Lillard won't be the last high-level player to come knocking, but there are only so many top-20 players who fight tooth and nail for Miami and only Miami. The Heat didn't deliver.
Now the Bucks are towering title favorites in the East. Jimmy Butler gets another year older and the Heat's supporting cast looks worse than last season. Miami's 2023 Finals run was built on a rather improbable hot spell from 3-point range. Don't count on a statistical anomaly to save them again. Miami was the No. 8 seed last season, a team riddled with plenty of glaring holes. To get Dame without giving up either Butler or Adebayo would have truly kept the Heat on the map. Now, the reigning conference champs feel like afterthoughts.
This will all sound silly when the next superstar demands a trade to Miami, but the Heat have missed out on a string of potential stars to pair with Butler and Adebayo. Blockbuster trade requests are the way of the NBA world nowadays, but Dame represents a huge failure on the part of Miami's front office. Maybe the Blazers simply preferred Ayton to Herro and that's that, but it's clear the Heat never made their best offer. Whether that was strategic or a misfire in judgement, we may never know. All we do know is that it was a mistake.
