Boston Celtics end up winners of Damian Lillard trade after Bucks loss

BOSTON — When the Bucks traded for Damian Lillard before the 2023-24 season, not only did it shock the NBA world, but it was clearly a message sent to Giannis Antetokounmpo. The Bucks had floundered since winning the 2021 NBA title, and with an aging core, Milwaukee elected to trade for Lillard from Portland in a stunning deal.

Lillard had long been rumored to prefer the Heat as a landing spot at the time. Back then, Miami was fresh off winning the East in 2023. While the assets were a major question mark, it was no secret Lillard wanted to be a part of the Heat. But instead, the Bucks made the huge three-team trade that also sent Jrue Holiday to Portland.

Turns out, the Celtics came out the real winners of that Lillard deal. Not only did they not see their hated rival in the Heat end up with Lillard, they landed Holiday by making a separate deal with the Trail Blazers. The C’s dealt for the All-Star guard right before the start of training camp, giving them a formidable core as they dealt away depth pieces in Robert Williams and Malcolm Brogdon, plus draft assets.

Holiday was a key piece for the Celtics to win the 2024 NBA championship to get back to the mountaintop. While Holiday was leaned on as a huge offensive contributor with the Bucks, he was one of the many quality players for the Celtics. He was the lone champion on the roster last season and helped the C’s hang Banner No. 18.

On the flip side, the Heat and Bucks look like disasters now. Both teams were main playoff rivals earlier in the decade but bowed out in 2025 unceremoniously. The Heat were swept by the Cavaliers in the first round in the most lopsided series in NBA playoffs history. The Bucks lost to the Pacers in five games, including a stunning collapse in overtime to put a bow on their season.

Antetokounmpo’s future is uncertain in Milwaukee considering the team’s mediocrity despite MVP-level play. Lillard tore his left Achilles tendon in Game 4, and at 34, his NBA future is murky. While Antetokounmpo is still at the height of his powers, the supporting cast simply isn’t good enough in Milwaukee. Fans need to squint to see who’s left from the 2021 title squad as the Bucks enter a potentially-transformational offseason.

The Heat aren’t in a much better position. They shocked the East and the Celtics on their way to the 2023 NBA Finals. But since then, they’ve lost in the first round the past two playoffs. Their drama with star Jimmy Butler was well-chronicoled during the season before shipping him to Golden State. And now, the Heat have to watch “Playoff Jimmy” star for the Warriors from home as their roster is also in a state of flux.

That’s life in the NBA; situations change in an instant. While both the Heat and Bucks are mired in uncertainty, the defending champion Celtics march onto the second round after blowing out the Magic in Game 5. It’s unclear if the C’s will repeat as champs this season, but their roster is set up to compete beyond the 2025 playoffs. That’s a far, far cry from their rivals in the Heat and Bucks.

• Jayson Tatum makes candid admission after Boston Celtics series win vs. Magic
• Boston Celtics unlock dream scenario after Magic Game 5 rout
• Boston Celtics star passes critical tests in series win over Magic
• So far, Celtics’ killer instinct is better than it was in 2024 title run