While Damian Lillard has spent more than half a season with the Bucks, seeing him in anything other than a Trail Blazers uniform is still jarring.
Lillard’s tenure in Portland was fruitful. Over 11 seasons, he became the franchise’s all-time scoring leader, earned a selection to the NBA’s 75th Anniversary Team, led the Blazers to eight playoff appearances and earned a reputation for clutch play. due to countless memorable moments at the end of the game.
In the 2023 offseason, Lillard’s time with the Blazers came to an end when he was traded to the Bucks as part of a blockbuster three-team deal. And although many saw the trade as an inevitable reality, the news still sent shockwaves through the basketball world.
Why did the Trail Blazers trade Lillard? Review the events and reports that led to Portland’s decision to part ways with its franchise player.
Why did the Trail Blazers trade Damian Lillard?
The Trail Blazers traded Lillard to honor a commercial application He did it on July 1.
During the 2022-23 season, there were rumors that Lillard’s time in Portland could be coming to an end. While Lillard had the best statistical season of his career, he appeared in only 58 games and the Blazers finished with a 33-49 record.
Lillard, who would turn 33 during the 2023 offseason, fully expressed that he was not interested in being part of a rebuilding franchise. Portland, however, had signaled a rebuild by bringing in young talent through the draft, a group that includes point guard Scoot Henderson, the third overall pick in the 2023 NBA Draft.
In the time leading up to Lillard’s request, he was said to have been in constant communication with Portland’s front office regarding the direction of the organization.

Immediately following Lillard’s request, it was reported that his preferred destination was Miami. Later, Lillard’s agent, Aaron Goodwin, suggested that his client would not fulfill his contract with any other team. This resulted in the NBA sending a memo to all 30 teams that served as a warning to Lillard and Goodwin.
While Lillard’s trade to the Heat was at one point seen as a foregone conclusion, no real progress was ever made in negotiations as Portland was unimpressed with Miami’s trade offers. Nearly three months after the request, the Trail Blazers agreed to trade Lillard to the Bucks as part of a three-team deal on September 27.
After the trade, TNT Sports’ Chris Haynes detailed the “messy divorce” between the two parties, reporting that Lillard was willing to rescind his request, but Trail Blazers general manager Joe Cronin told Lillard there was “no turning back.”
In a Washington Post interview Before the season, Cronin had this to say about the decision to trade Lillard: “Our directions didn’t match up. Things didn’t work out. We had pure intentions in our desire to build a winner around him. We just couldn’t get it done. Take him away. I don’t think that it was a lie. We just couldn’t do it.”
Damian Lillard contract details
Lillard is under contract through at least the 2025-26 season. He has a player option for the 2026-27 season in which he could earn more than $63 million by the age of 36.
| Season | Age | Salary |
| 2023-24 | 33 | $45,640,084 |
| 2024-25 | 3. 4 | $48,787,676 |
| 2025-26 | 35 | $58,545,211 |
| 2026-27 | 36 | $63,228,828 |