In a blockbuster move Wednesday, the Portland Trail Blazers agreed to trade star guard Damian Lillard to the Milwaukee Bucks, pairing Lillard with two-time MVP Giannis Antetokounmpo and immediately forming one of the most prolific duos in the NBA.
The full details of the three-team trade, which also included the Phoenix Suns:
Lillard’s trade out of Portland may have been a long time coming, but offseason developments accelerated the seven-time NBA All-Star’s ask to leave the franchise where he’s spent more than a decade.
Earlier this offseason, Lillard — who’s making $45.6 million this year — made it clear he preferred to play for the Eastern Conference champion Miami Heat, a position that led to the NBA issuing a memo to all 30 teams warning against a one-team trade demand.
But what led to the fizzling between the Blazers and their longtime cornerstone point guard? And how did he end up in Milwaukee rather than Miami? Here’s a timeline of the events.
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2021-2023: The seeds are planted
The first signs of Lillard’s eventual separation with the Blazers appear as far back as 2021, after Portland suffers a first-round playoff defeat to a Denver Nuggets team missing Jamal Murray due to injury. As The Athletic’s Jason Quick wrote:
The lowest of lows for Damian Lillard was in the summer of 2021, on the heels of an embarrassing playoff loss to the Denver Nuggets. In the nights that followed the first-round exit, he said he couldn’t sleep. His insomnia wasn’t because he was eliminated by a Nuggets backcourt that started Facundo Campazzo and Austin Rivers, it was because he questioned if the people around him in the Blazers organization cared about the loss as much as he did.
That summer triggered a switch in Lillard. Suddenly, it seemed, an organization that did everything for him — his approval and opinion were sought on everything from player moves and coaching hires, to practice times and plane departures — wasn’t doing enough.
So he began to voice his displeasure, first internally and then publicly, albeit in ways that would allow Lillard to proclaim no one ever heard it from his mouth, thus protecting him from backlash. He felt the Blazers should have been giving him more help with the roster, a feeling that only heightened that summer as he watched P.J. Tucker win a ring with the Milwaukee Bucks in July 2021.
Still, Lillard remains publicly committed to Portland, even as the Blazers suffer back-to-back losing seasons. That would soon change.
April 9, 2023: Blazers finish losing season, Lillard wants chance to ‘go for it’
Portland closes the 2022-23 season with a 33-49 record, capping the campaign with a 56-point loss to the Golden State Warriors at home. Despite the team’s losing season, Lillard, who missed most of the previous campaign with an abdominal injury, posts a career-highs in points (32.2), 3-pointers made (4.2) and attempted (11.3) per game, and ties his career-best field goal percentage (46.3 percent). He says he doesn’t want Portland to draft another young player and wants proven veterans who can immediately help the team.
“I’m just not interested in that,” Lillard says of adding another young player. “That’s not a secret. I want a chance to go for it. And if the route is to (draft youth), then that’s not my route.”
General manager Joe Cronin and coach Chauncey Billups express similar sentiments and appear aligned with Lillard’s thinking.
“We don’t want to go through this anymore,” Cronin says. “It’s time for us to start winning basketball games.”
Billups adds: “We’ve done the tweak thing. A few times. We’ve got to be more aggressive than that. If we want to actually do right by the best player in the history of the organization, we have to be aggressive.”
May 16, 2023: Portland lands third pick in NBA Draft Lottery
The Trail Blazers leap up to secure the third pick in the 2023 NBA Draft, finishing behind the San Antonio Spurs and Charlotte Hornets in the 2023 NBA Draft Lottery. While the Spurs selecting French phenom Victor Wembanyama seems to be a foregone conclusion, there’s uncertainty over who the Hornets will pick between forward Brandon Miller or point guard Scoot Henderson. Portland’s fortune means the team must decide if it wants to draft an elite prospect rather than move the pick for a proven veteran to help Lillard.
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Lillard has indicated he ‘wants to win now’ and drafting youth is ‘not my route’
June 7, 2023: Miami, Brooklyn ‘obvious’ choices for Lillard, if traded
A clip of Lillard recording a podcast with Showtime goes viral, in which Lillard is asked which team — between the New York Knicks, Miami Heat, Boston Celtics or Brooklyn Nets — he would prefer to play for if traded. He responds, “Miami, obviously. Miami is the obvious one, and Bam (Adebayo) is my dawg. Bam is my dawg, for real.”
He adds, “Brooklyn is another obvious one cause Mikal Bridges is my dawg, too.”
June 22, 2023: Portland drafts youth
After the Spurs take Wembanyama at No. 1 and the Hornets select Miller at No. 2, the Trail Blazers elect to keep the No. 3 pick and select 19-year-old Henderson. They also draft then-22-year-old Kris Murray, a forward out of Iowa, in the first round (No. 23) and 19-year-old shooting guard Rayan Rupert in the second round (No. 43). Although the move for Henderson appears to solidify the Blazers’ backcourt of the future with him and 2022 first-rounder Shaedon Sharpe, it also presents obvious questions about Lillard’s future with the franchise.
Cronin says selecting Henderson would be more impactful than any trade for veteran help.
“I would say we made the biggest move possible by drafting Scoot Henderson,” Cronin says. “He’s going to be better than any player that would maybe be perceived as that big move. And then you start to factor in other things that matter in this league — the salary cap, (Henderson) on a rookie scale — that allows us to build a lot more depth than we would have been able to otherwise.”
Cronin also says that while gathering his draft intel, he made inroads on possible deals ahead of the looming free agency period.
“There’s still a lot of movement to be had,” Cronin says. “We’ve planted a lot of seeds on deals. The goal now is to add some veteran players who can continue to ramp up this team.”
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Trail Blazers think they made move that trumps any trade in drafting Scoot Henderson
June 23, 2023: Will Smith’s ‘Miami’ song ‘just a coincidence’ on Lillard’s IG Live, agent says
A clip of captured video from Lillard’s Instagram Live goes viral in which he’s seen smiling and laughing at a club in Paris while listening to Will Smith’s song, “Miami,” hours after the NBA draft. Lillard’s agent, Aaron Goodwin, tells The Athletic that the music was “just a coincidence” and the DJ, presumably, was making light of the player’s uncertain situation.
“Damian’s not disrespectful,” Goodwin says. “He’s not an instigator, so he’s not going to do anything out of character. There would be no reason for him to do that. That’s why he laughed (in the video). It’s a funny coincidence that a DJ would put that on.”
The DJ also played Whitney Houston’s classic, “I Wanna Dance With Somebody,” which includes the lyric, “I wanna feel the heat with somebody.”
June 26, 2023: Blazers ‘remain committed to building a winner’ around Lillard
Cronin says in a statement that the team remains “committed to building a winner” around Lillard. The GM says he met with Lillard and Goodwin that day and the trio “had a great dialogue.” (Goodwin negotiated Lillard’s two-year, $122 million extension he signed with Portland in July 2022, which kept him under contract through 2026-27 season.)
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Quick: On Damian Lillard’s future, and the simple concept that solves his angst
Joe Cronin talks with Damian Lillard of the Portland Trail Blazers prior to the game against the Charlotte Hornets at Moda Center in December 2021 in Portland, Ore. (Photo: Soobum Im / Getty Images)
July 1, 2023: Lillard requests trade to Heat
As NBA free agency opens, Lillard requests a trade out of Portland, specifically to Miami, where he could team up with Jimmy Butler and Adebayo. The trade request isn’t a total surprise. Several reports, including that of The Athletic’s Sam Amick, had the Heat as Lillard’s top choice. Other teams that have interest include the Philadelphia 76ers, LA Clippers and Utah Jazz.
“We have been clear that we want Dame here but he notified us today he wants out and he’d prefer to play someplace else,” Cronin says in a statement. “What has not changed for us is that we’re committed to winning, and we are going to do what’s best for the team in pursuit of that goal.”
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July 10, 2023: Cronin addresses Lillard situation, says he ‘failed’ guard
Cronin says he “failed” Lillard, adding that he wishes he had more time to make trades.
“I don’t feel that I did everything I could because I didn’t get done what I needed to get done,” Cronin says at the Las Vegas Summer League. “In that sense, I do feel like I failed Dame. Our goal was to win now as quickly as possible. If he didn’t feel that way, it was a failure on my end.”
Cronin adds that “building around Dame has always been the goal, all the way even through the draft,” but the team had difficulty finding the right deals.
“The previous two years we drafted at seven (Sharpe) and we drafted at three (Henderson) … in the meantime, we were scouring the market looking for more win-now players. What kept happening was those players were just not available.
“Each time we tried to weigh that — in Shaedon’s draft, pick seven, what does that look like versus what’s available in the market? And the answer was obvious: Shaedon is better. Same thing happened this time, what does pick three look like versus the return to market? It wasn’t close; had to go three.
“So it wasn’t necessarily intentional, it was just doing what is best for this team. And we kept doing that and I could see why, you know, Dame would look at it and say this isn’t a win-now opportunity. … From that regard, I understand his position, and I respect it, and it makes sense to me why he would look elsewhere.
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Joe Cronin Q&A: The Trail Blazers GM on the future of Damian Lillard
Cronin also says he will be patient in finding the best return for the Blazers while seeking to trade Lillard.
“We’re going to do what’s best for our team,” Cronin says. “We’re going to see how this lands. And if it takes months, it takes months.”
Regarding whether he’s prepared to have Lillard on the roster if a deal isn’t found, Cronin says, “The goal is to always have Dame as a Trail Blazer — always was and always will be.”
“We wanted him to retire a Trail Blazer,” he says. “So we are very open-minded to any time Dame wants to be a part of us.”
July 28, 2023: NBA sends memo to all teams regarding Lillard’s trade request to only Heat
The NBA informs all 30 teams that they interviewed Lillard, who turned 33 on July 15, and Goodwin about Lillard’s reported stance that he only wants to play for the Heat, league sources confirm to The Athletic on July 28. The league advises Lillard and Goodwin that any future comments “suggesting Lillard will not fully perform the services called for under his player contract in the event of a trade” will be subject to discipline, as will any similar comments by players or agents in the future.
“Recent media reports stated that Damian Lillard’s agent, Aaron Goodwin, called multiple NBA teams to warn them against trading for Lillard because Lillard’s only desired trade destination is Miami,” the memo says. “Goodwin also made public comments indicating that Lillard would not fully perform the services called for under his player contract if traded to another team.
“We interviewed Goodwin and Lillard and also spoke with several NBA teams to whom Goodwin spoke. Goodwin denied stating or indicating to any team that Lillard would refuse to play for them. Goodwin and Lillard affirmed to us that Lillard would fully perform the services called for under his player contract in any trade scenario. The relevant teams provided descriptions of their communications with Goodwin that were mostly, though not entirely, consistent with Goodwin’s statements to us.”
The memo essentially shows the NBA backs the Trail Blazers’ stance that there should be open bidding for Lillard’s rights, and warns other players and agents that a one-team trade demand won’t be tolerated.
Aug. 1, 2023: Heat working on Lillard trade package, but no real traction on deal
A month after Lillard’s trade request, there is no real traction on any kind of a deal, The Athletic reports. Lillard’s goal of playing the Heat hasn’t changed, and Miami has been working on a trade package that could include three to four first-round picks — with Tyler Herro going to a third team for assets — expiring contracts, a young player such as Nikola Jović and potentially second-round picks and draft swaps, per sources involved in the discussions.
Sept. 25, 2023: Raptors enter the bidding
With training camp approaching and the Heat and Blazers remaining far apart on any potential Lillard trade, Portland begins re-engaging with other teams about a potential Lillard move. One team that begins to gain buzz is the Toronto Raptors, though their offer does not include prized third-year forward Scottie Barnes. It’s unclear how serious those discussions ended up.
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Sept. 27, 2023: Blazers trade Lillard to Bucks in 3-team deal with Suns
Lillard’s finally on the move, and it’s not to the Heat or even a team that was rumored to be interested in acquiring him.
The Milwaukee Bucks agree to a deal with the Blazers and Suns to acquire Lillard. Portland gets Holiday, Ayton, Camara, a 2029 Bucks first-round pick and a Bucks pick swap. Phoenix gets Nurkic, Little, Johnson and Allen.
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(Photo: Sam Forencich / NBAE via Getty Images)
