Damian Lillard trade has 3 big winners, and 4 real losers

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Let’s give out winners and losers from the blockbuster Damian Lillard trade.

Damian Lillard’s trade request was the NBA storyline that just wouldn’t end. For three months, Lillard’s trade request was stuck at the same crossroads: the superstar guard claimed he only wanted to play for the Miami Heat, but his Portland Trail Blazers had no interest in anything they could offer.

On Wednesday, out of nowhere, a mystery team emerged to land Lillard and change the 2024 NBA championship picture all at once.

The Milwaukee Bucks acquired Lillard in a three-team trade with the Trail Blazers and Phoenix Suns. Portland is landing Jrue Holiday (who is expected to be flipped in another trade), an unprotected Bucks pick in 2029, and first round swaps in 2028 and 2030. The Blazers are also adding Deandre Ayton while sending Jusuf Nurkic and Nassir Little to the Suns, where they will be joined by Grayson Allen.

We’ve already graded this trade for every team involved. Now let’s hand out some winners and losers.

Winner: Giannis Antetokounmpo

Antetokounmpo delivered the Bucks their first NBA championship in 50 years with an all-time great run through the 2021 playoffs, capped off by a 50-point performance for the ages in the Game 6 clincher of the NBA Finals. Since then, the Bucks have fallen short in consecutive seasons, and were thrown into crisis after being on the wrong end of a 1-8 upset in the first round of last season’s playoffs by the Miami Heat.

Giannis spent his summer publicly telling the Bucks that he wasn’t going to be satisfied with one championship. If he couldn’t get another ring in Milwaukee, he said, he’d go to another team where it would be possible.

The Bucks’ bold trade for Lillard might not happen without Giannis’ threats. By trading for Dame, the Bucks are going all-in around Antetokounmpo with the intention of getting him to sign another extension in Milwaukee. Giannis has never had a teammate as talented as Dame, or played with anyone who is such a perfect fit next to him offensively.

The small market Bucks aren’t worried about the luxury tax or future draft picks out the door — they’re trying to maximize their championship window with the best player they’ve had since Kareem Abdul-Jabbar, someone on the path to being an all-time great in his own right. Giannis applied the pressure, and the Bucks delivered. That’s how it’s supposed to be done.

Winner: The Bucks’ 2024 championship chances

The Bucks were considered a championship contender even before the Dame trade, but it was hard to be confident in them. The first round collapse against the Heat cost head coach Mike Budenholzer his job, with Milwaukee hiring rookie head coach Adrian Griffin to replace him. The Bucks brought back Brook Lopez and Khris Middleton in free agency, but didn’t make any meaningful additions to the roster. They really needed Middleton to regain his All-Star caliber play to hit their ceiling after a couple down years because of injuries.

Not anymore. Lillard immediately makes the Bucks a juggernaut, solving their biggest on-court problems and allowing everyone else to slide into more appropriate roles. The Bucks’ half-court offense had been incredibly stagnant in big moments, as teams loaded up on Giannis’ drives to the basket and dared anyone else to beat them. Enter Lillard, perhaps the most deadly pick-and-roll guard alive. Milwaukee has never someone with this level of pull-up shooting and pick-and-roll dynamism in the Giannis era before. The defense will slip, but the offense just became so, so much scarier.

The Bucks are now the favorites in the East. They might be the favorites to win the championship. Lillard is simply a perfect on-court fit in Milwaukee, and the rest of the league’s contenders should be very, very afraid.

Loser: Miami Heat

The Heat have had a rough offseason since making a Cinderella run to the 2023 NBA Finals as a No. 8 seed. Miami lost Gabe Vincent and Max Strus in free agency, and their biggest addition was Josh Richardson on a small contract. The Heat had no reason to panic because a Dame trade seemed inevitable. Now that Lillard is in Milwaukee, the Heat are staring down a season that could see them take a real step back.

Lillard would have been a perfect fit on the Heat next to Jimmy Butler and Bam Adebayo. Either Portland didn’t want any of their assets, Miami didn’t make its best offer, or the Blazers decided they didn’t like the idea of Dame requesting a trade to only one team, and wrote Miami off because of it. Either way, seeing Dame land with an East rival in the Bucks is a nightmare scenario for the Heat. For as incredible as their postseason run last year was, it’s hard to imagine this team pulling it off again against a new and improved Bucks squad, and without some key contributors in Strus and Vincent.

Loser: Damian Lillard’s Miami dreams

Dame really wanted to play in Miami. Lillard called out the Heat on a podcast as the team he’d like to play for weeks before he actually requested a trade. As his trade request dragged on for three months, most people around the NBA assumed he’d eventually end up in Miami.

Milwaukee is about as far as it gets from South Beach, culturally. I think Dame will get over it quickly — now he’s playing for championships around a top-2 player in the world. There is still probably a small part of him that’s disappointed, though.

Loser: Eastern Conference parity

The East seemed wide open for the taking only 24 hours ago. Boston felt like the favorites, but they still had questions after trading Marcus Smart for Kristaps Porzingis. Milwaukee was replacing its very successful head coach. The Sixers had to deal with James Harden’s trade request. Meanwhile, the Pacers, Magic, and Hawks all seemed poised to take a step up.

Now, there’s a real powerhouse in the East again. Giannis and Dame is a problem without a solution if the players around them are healthy and locked in. Milwaukee’s biggest issues — halfcourt offense, pull-up shot-making from the perimeter — have been addressed, while the defense remains strong enough to insulate Lillard. The Celtics are still a real contender in the East, but it’s hard to say the conference is wide open anymore. There’s a true powerhouse here again with Lillard’s Bucks.

Winner: Deandre Ayton

Ayton’s inclusion in this deal is far from the headliner, but it’s a real piece of the Suns’ title dreams and the Blazers’ rebuild. Phoenix selected Ayton with the the No. 1 overall pick in the 2018 NBA Draft over Luka Doncic, and he was fantastic during the team’s run to the 2021 NBA Finals. Since then, the relationship between Ayton and the franchise had fractured, largely because he didn’t get along with former coach Monty Williams. With the Suns now having so many mouths to feed with Kevin Durant, Devin Booker, and Bradley Beal, Ayton was never going to get a huge share of offensive possessions. He quickly became the odd man out.

Still, I’m not sure where the upside in this deal comes for Phoenix. Jusuf Nurkic has been extremely unreliable the last few years, and doesn’t offer Ayton’s potential. It also feels like, by getting involved in this trade, the Suns helped one of their biggest competitors for the championship — the Bucks — move closer to a title.

The trade is a big win for Ayton either way. He moves to a young team in Portland without any pressure to win immediately. He should see the ball way more often as the team starts to build around Scoot Henderson and Shaedon Sharpe. Ayton still has ideal size and athleticism for a center — he just needs to play with more force. For a player who badly needed a change of scenery, moving to Portland could be the perfect fresh start.

Loser: Phoenix Suns

The Suns have a loaded roster and could still win the 2024 NBA championship. I personally believe they moved further away from the title goals with their inclusion in this trade for a couple reasons:

Ayton had plenty of issues as a player, but he offered way more upside than Nurkic in the middle. Perhaps Frank Vogel could have repaired a relationship frayed by Monty Williams in recent years. Even if Phoenix was determined to trade him, I think they could have gotten a better return than an uninspiring, older center and a few questionable role players.
Phoenix getting into this trade made one of its biggest rivals in the Bucks even stronger. Would Portland have sent Lillard to Milwaukee if they couldn’t get Ayton? I’m not so sure. Now Milwaukee is ahead of Phoenix in the championship pecking order in my opinion, and it was all made possible by the Suns getting in this trade to ditch Ayton.
Jrue Holiday is going to be traded to a contender soon. It’s possible the Warriors trade Chris Paul, Jonathan Kuminga, and a pick for him. It’s possible another Western Conference team pulls off a similar deal. Either way, with Holiday now on the trade market, there’s going to be another contender that adds a great piece to go up against the Suns.

It’s totally possible this take will blow up in my face, and Devin Booker and Kevin Durant will lead the Suns to their first championship in franchise history. For now, though, I’m skeptical moving Ayton in the Dame trade gets Phoenix closer to a title.