Damian Lillard’s goal was ultimately fulfilled. Mostly. The seven-time All-Star guard is reportedly being acquired by the Milwaukee Bucks from the Portland Trail Blazers as part of a three-team trade with the Phoenix Suns.
In exchange, the Blazers will receive Jrue Holiday, Deandre Ayton, and Toumani Camara in addition to the Bucks’ unprotected first-round selection in 2029 and their unprotected swap rights in 2028 and 2030. Jusuf Nurki, Grayson Allen, Nassir Little, and Keon Johnson join the Suns.
Lillard made a trade request on the second day of free agency in 2023 after years of what seemed like back-and-forth negotiations with Portland over how to assemble a championship-caliber team around him. In the summer of 2022, he agreed to a contract extension with a two-year maximum. Over the following four seasons, Lillard is due $216.2 million in payments, including $63.2 million in the 2026–27 season.
Lillard had a career-high scoring average of 32.2 points per game last year after struggling with injuries for much of the previous two seasons. During that time, he missed 77 games, which is double the amount of games he missed in his first ten seasons combined. The previous two seasons, the Trail Blazers failed to make the playoffs.
Lillard guided the team to eight postseason outings, including one that saw them advance to the Western Conference finals in 2018–19. Even with the best player in team history, the Blazers frequently endured first-round exits and were never able to reach the top of the league.After surpassing Clyde Drexler in 2022, Lillard leaves Portland as the Blazers’ all-time top scorer (19,376 points), as well as the club leader in made 3-pointers, made free throws, and scoring average.
Lillard’s commitment to Portland was one of the NBA’s most frequently brought up topics by this point. However, after a poor end to the 2020–21 campaign, rumors regarding whether he would ever leave for brighter pastures rose to new heights.
The Blazers lost to the Nuggets in the first round in six games, marking their fifth Round 1 exit in eight postseason appearances under head coach Terry Stotts. This happened despite Denver playing without injured star guard Jamal Murray, despite Damian Lillard scoring 55 points on 24 shots in a crucial Game 5 that Portland lost in double overtime, and despite Portland holding a 14-point lead in Game 6 at halftime. Lillard made it clear in his on-the-record remarks following that demoralizing loss that he expected the Blazers front office and then-general manager Neil Olshey to act with greater urgency in their resumed pursuit of championship contention.
Olshey sacked Stotts and hired Chauncey Billups, a first-time head coach, in his place. He also re-signed swingman Norman Powell to a five-year, $90 million contract and added Cody Zeller, Tony Snell, and Ben McLemore to the roster as rotational depth players. (The Blazers fired Olshey a few months later, alleging transgressions of the team’s code of conduct discovered during an inquiry into workplace wrongdoing within the company.) Without substantial additions, and with Lillard missing a career-low 29 games due to an abdominal injury that later required surgery, Portland fell to a 27-55 record, setting the setup for what Lillard called a “critical summer” During which he agreed to extend his previous supermax contract for an extra two years at a cost of $122 million