Damian Lillard traded to Bucks after 11 seasons with Portland Trail Blazers

Damian Lillard finally got his wish. Mostly. The Milwaukee Bucks are acquiring the seven-time All-Star guard from the Portland Trail Blazers in a three-team deal with the Phoenix Suns, the team announced Wednesday night.

As part of the deal, Jrue Holiday, Deandre Ayton and Toumani Camara are going to the Blazers, as well as the Bucks' 2029 unprotected first-round pick and unprotected swap rights in 2028 and 2030. The Suns land Jusuf Nurkić, Grayson Allen, Nassir Little and Keon Johnson.

Lillard requested a trade on the second day of 2023 free agency after years of seemingly going back and forth with Portland on trying to build a championship contender around him. He signed a two-year, max contract extension in the summer of 2022. Lillard is owed $216.2 million over the next four seasons, including $63.2 million in the 2026-27 campaign.

Lillard averaged 32.2 points per game last season, a career high, in a resurgent season after injuries hampered him for stretches of the past two seasons, missing 77 games in that stretch, double the games he missed over the first 10 seasons of his career. The Trail Blazers missed the postseason the past two seasons.

Lillard led the franchise to eight postseason appearances, making it to the Western Conference finals in the 2018-19 season. However, the Blazers mostly suffered first-round exits and could never make it to the pinnacle of the league despite having its best player in franchise history.

Lillard leaves Portland as the Blazers' all-time leading scorer (19,376 points), passing Clyde Drexler in 2022, and the franchise leader in 3-pointers made, free throws made and scoring average.

Why Damian Lillard is leaving the Portland Trail Blazers

Lillard’s loyalty to Portland had long since become one of the NBA’s most frequently repeated talking points. But speculation about whether he’d one day seek greener pastures reached new heights following a disappointing end to the 2020-21 campaign.

The Blazers bowed out to the Nuggets in six games in the first round — their fifth Round 1 exit in eight postseason appearances under head coach Terry Stotts — despite Denver playing without injured star guard Jamal Murray, despite Lillard putting up 55 points on 24 shots in a pivotal Game 5 that Portland lost in double overtime and despite holding a 14-point second-half lead in Game 6. After that dispiriting defeat, Lillard delivered loud and clear on-the-record comments about how he wanted to see increased urgency from then-general manager Neil Olshey and the Blazers’ front office in renewed pursuit of championship contention.

What followed underwhelmed: Olshey fired Stotts, replacing him with first-time head coach Chauncey Billups; brought back swingman Norman Powell on a five-year, $90 million deal; and signed Cody Zeller, Tony Snell and Ben McLemore as rotation ballast. (The Blazers fired Olshey a couple of months later, citing violations of the team’s code of conduct uncovered in an investigation of workplace misconduct within the organization.) Without significant reinforcements, and with Lillard struggling through an abdominal injury that would eventually require surgery, limiting him to a career-low 29 games, Portland plunged to a 27-55 record, setting the stage for what Lillard called a “critical summer” … during which he signed a $122 million extension to his previous supermax deal to stay under contract in Portland for two additional years.

Healthy again, Lillard turned in a career year last season, finishing third in the NBA in scoring at 32.2 points per game and 10th in facilitating at 7.3 assists a night. That wasn’t nearly enough to lift the Blazers out of the doldrums, though, as Portland stumbled to a 33-49 mark and another lottery pick — this time, third overall. Landing the No. 3 selection forced new Blazers GM Joe Cronin into a difficult choice. Would he dangle that enticing trade chip, and potentially talented young players like Anfernee Simons or Shaedon Sharpe, in search of established veterans who could help build a more competitive roster around Lillard? Or was it better to sit tight and take the pick, continuing to build out Portland’s young core — while also knowing that committing to the path of rebuilding might lead Lillard to finally ask out?

The draft came and went. The Blazers kept the pick, drafting G League Ignite star Scoot Henderson — a 19-year-old über-prospect who just happens to play Lillard’s position. Lillard and his agent, Aaron Goodwin, met with Cronin to discuss the future; Lillard reportedly said he’d wait to see what Cronin and Co. did at the start of free agency before making any decisions.

As soon as free agency opened, Portland gave Jerami Grant $160 million. The following morning, Lillard requested a trade from the only franchise he’s ever known.

The Blazers said they wanted to accommodate that request. But the fact Lillard had pegged Miami as the only place he wanted to go — and that his representatives were trying to depress the market by scaring off other potentially interested suitors, telling them they’d be getting an unhappy Dame if they dealt for him — complicated matters. (The NBA later sent all 30 teams a memo emphasizing any comments suggesting a player “will not fully perform the services called for under his player contract in the event of a trade” will be subject to league discipline.)

The most frequently theorized packages for Miami to send to the Pacific Northwest were headlined by former Sixth Man of the Year Tyler Herro. But adding another combo guard who’d cannibalize touches and playmaking opportunities for Simons, Sharpe and Henderson didn’t seem all that enticing to the Blazers … which is why Portland reportedly preferred constructions that would move Herro to a third team … which, with Herro just about to start a four-year, $120 million contract extension, profiled as a tricky bit of business.

And so: a holding pattern. The Blazers, who’d hoped for a return for Lillard on the order of what the Timberwolves gave up for Rudy Gobert or the Suns forked over for Kevin Durant, didn’t like Miami’s offer enough to quickly consummate a deal. The Heat, seeing no other actual offers on the board, felt no compulsion to bid against themselves and add any sweeteners to their package. And with Lillard having signed that extension to keep him under team control through at least the summer of 2026, the Blazers represented a willingness to just hunker down and wait for something better.

That made sense. The nearest pseudo-deadline in the proceedings was when NBA teams reconvene for media day on Monday ahead of the start of training camp. (Even the question of which camps Lillard would be willing to report to spurred a little drama.) Sure enough, ESPN’s Adrian Wojnarowski reported in mid-September the Blazers had “done a lot more talking with teams in the [previous two weeks] than they did probably in at least a month-plus prior,” with their sights set on constructing multi-team deals that could net a larger package of draft picks and young players than a straight one-to-one swap with Miami would offer.

Lillard, for his part, said during multiple media appearances that while “in a perfect world” he’d love to stay in Portland, he can’t help seeing himself and the Blazers organization moving in different directions.