Who could have seen this happening? After months of the Damian Lillard saga with the Portland Trail Blazers, the Bucks made a surprising move to acquire the seven-time All-Star.
The Bucks traded Jrue Holiday, Grayson Allen, a 2029 first-round draft pick and agreed to swap picks in 2028 and 2029 in a three-team trade involving the Blazers and Suns, according to ESPN reporter Adrian Wojnarowski.
“We have been clear that we want Dame, but he notified us today he wants out and he’d prefer to play someplace else,” Trail Blazers general manager Joe Cronin said in a statement.
The trade request wasn’t a complete surprise, though. Earlier in his career, Lillard had significant success in clutch playoffs situations, earning him the nickname “Dame Time.”
However, after key teammates like CJ McCollum and LaMarcus Aldridge departed the team in recent seasons, the Blazers encountered numerous challenges in maintaining competitiveness. They failed to secure a playoff spot in the last two seasons and were eliminated in the first round of the playoffs in the two seasons before that.
This past season, the Blazers had some luck in the draft lottery, securing the second overall pick. They were poised to select promising prospect Sterling “Scoot” Henderson from the G League Ignite. Lillard wanted to trade the pick to acquire another star player to join him in Portland. The Blazers did not comply with that request.
What caught everyone off guard in the Lillard trade was that he did not get traded to the Miami Heat, despite his early insistence that he would only play for them, making teams hesitate to trade for him.
The Heat also were the best fit for Lillard because the franchise needed a “bucket-getting” guard. The Heat were sixth worst in the league in offensive rating for the 2023 regular season, according to Statmuse.
As talks between the Heat and Trail Blazers stalled, the Bucks swooped in to acquire Lillard. Even though Lillard didn't land in Miami, he embraced the chance to play for Milwaukee, given his strong friendship with Bucks star Giannis Antetokounmpo.
In the past, Lillard had expressed his desire to team up with Antetokounmpo. In December 2022, when asked which player he would choose to help win an NBA championship, he responded, "I would pick Giannis."
Lillard’s trade is great for the Bucks, especially because Antetokounmpo made it clear that he would consider leaving the team to chase a championship elsewhere. This was especially concerning for the Bucks because he still needed to sign a new contract extension. With this trade, it's likely that Giannis will stick with the Bucks to focus on winning a championship in Milwaukee.
Offensively, the Bucks are now loaded with a three-headed monster of Lillard, Antetokounmpo, and Khris Middleton. The pick-and-roll combination between Lillard and Antetokounmpo is expected to be one of the most challenging plays for opposing teams to defend in the NBA next season, further strengthening the Bucks' championship hopes.
For the Blazers, this is a great haul. The Blazers can focus on building their new star core of Anfree Simmons, Shaedon Sharpe, Sterling Henderson and newly acquired young talent in Deandre Ayton. The Blazers also have a great player in Jermai Grant, who they can leverage in trade conversations.
The blazers received all-star Jrue Holiday from the Bucks, whom they also flipped to the Celtics in exchange for young talent in Robert Williams and veteran Maclom Brogdon with two 1st overall picks.
Lillard’s return to Portland on January 31, 2024, is anticipated to be an emotional and heartfelt moment, considering his significant contributions to the city of Portland. Holiday will make his return to Milwaukee on January 11, 2024, with the Celtics.
