After 11 loyal seasons with the Portland Trail Blazers, Damian Lillard finally got what he had long resisted: a ticket out.
In a blockbuster three-team trade completed in September 2023, Lillard was sent to the Milwaukee Bucks, sending shockwaves through the NBA and instantly reshaping the power dynamics of the Eastern Conference. It marked the end of an era in Portland — and the beginning of a new, high-stakes chapter in Milwaukee’s title pursuit.
🧨 The Trade That Shook the League
The final deal, which came after months of speculation and a trade request by Lillard, was one of the biggest of the offseason:
Milwaukee Bucks received:
Damian Lillard (from Portland)
Portland Trail Blazers received:
Jrue Holiday (later flipped to Boston)
Deandre Ayton (from Phoenix)
Toumani Camara
2029 unprotected first-round pick (from Milwaukee)
Two pick swaps
Phoenix Suns received:
Jusuf Nurkić
Grayson Allen
Nassir Little
Keon Johnson
For the Bucks, it was an all-in move to maximize the championship window of Giannis Antetokounmpo, who had made subtle but pointed remarks in the offseason about wanting to see more urgency from the front office. Acquiring Lillard — one of the game’s most feared scorers — was the answer.
> “This is a dream scenario,” Lillard said at his introductory press conference. “To play next to someone like Giannis, in a city with championship aspirations? That’s exactly what I’ve been working for.”
🏀 The Dame-Giannis Effect
While the Bucks lost an elite two-way guard in Jrue Holiday, they gained what they had long needed: a true offensive closer.
Lillard averaged 24.3 points and 6.5 assists in his first season with Milwaukee. His ability to hit deep, contested shots opened up the floor for Giannis and transformed the Bucks’ late-game offense, which had previously struggled in the postseason under defensive pressure.
Their pick-and-roll action became unguardable, with defenders forced to choose between containing Giannis’ downhill power or Lillard’s pull-up threat from 30 feet.
Even with both stars battling minor injuries throughout the season and playoffs, the Bucks remained a top contender and reclaimed their spot as one of the most dangerous duos in the league.
🧭 What It Meant for Portland
For the Trail Blazers, the trade marked the end of an emotional era. Lillard had become synonymous with Portland — a loyal star who stayed committed through multiple rebuilds, coaching changes, and playoff heartbreaks.
He left the franchise as:
All-time leading scorer
7× All-Star
Beloved community icon
One of the league’s most respected leaders
In return, Portland embraced a full rebuild. They handed the keys to Scoot Henderson, Anfernee Simons, and Shaedon Sharpe, and reshaped the roster around youth and long-term growth.
The post-Dame era is still in its early stages, but with Ayton anchoring the frontcourt and promising guards in place, Portland has a clear direction — and no pressure to rush the process.
🌍 Impact on the Eastern Conference
Lillard’s move didn’t just impact the Bucks — it had ripple effects across the East.
The Boston Celtics, after acquiring Jrue Holiday from Portland in a follow-up deal, became Milwaukee’s biggest rival again — and eventually defeated them in the 2024 playoffs.
The Philadelphia 76ers and Miami Heat — who heavily pursued Lillard — were left scrambling.
The Bucks instantly became the betting favorite in the East after the trade.
While Milwaukee didn’t win the title in Year 1 of the Dame-Giannis era, the foundation is in place — and with more time to build chemistry, the duo could still deliver the franchise’s second championship in four years.
