As the NBA’s offseason calendar shifts to September and sees no trade to his preferred trade destination of the Miami Heat, Damian Lillard has integrated himself back into the Portland Trail Blazers ecosystem. For the last two weeks, team sources said Lillard has been working out at the Blazers’ practice facility, interacting with players and coaches.
Almost three months after his trade request, has there been a reconciliation of affairs? No, but Lillard wants the Blazers to know he’s willing to stay patient as his uncomfortable exit plays out.
In a call between Lillard’s agent, Aaron Goodwin, and Blazers general manager Joe Cronin earlier this month, it was made known that Lillard would be content to rejoin Portland for training camp. Lillard has informed the Blazers that he is ready to be fully fit for the start of the 2023-24 season, if only to give the organization more time to work toward a potential trade with the Heat, sources in those talks said. . But according to league sources, Cronin expressed skepticism about that approach. The Blazers are determined to get a deal done before camp begins.
For the next two weeks, the Blazers’ focus has turned to trading Lillard before the start of training camp and media day on Oct. 2 — and removing the speculation and what they believe is a cloud over the organization. Cronin and his front office landed tremendous young talent in Scoot Henderson and Shaedon Sharpe, and the Blazers are poised for a drama-free camp.
So the Blazers made the long-awaited blockbuster trade Wednesday, trading Lillard to the Milwaukee Bucks in a three-team deal that sent Jrue Holiday, Deandre Ayton, Toumani Camara, a 2029 first-round Bucks pick and two Bucks pick swaps in 2028 and 2030 in Portland. Jusuf Nurkić, Nassir Little, Keon Johnson and Grayson Allen are headed to Phoenix.
The trade has massive implications for the NBA landscape. The Bucks are now one of the favorites to win the 2024 championship, pairing Lillard with Giannis Antetokounmpo, Khris Middleton, Brook Lopez, NBA Sixth Man of the Year candidate Bobby Portis and shooters Pat Connaughton and Malik Beasley.
Then he made public comments about being unsure of the Bucks’ aspirations to contend for a title and unsure himself of signing an extension, Antetokounmpo was outplayed by an All-NBA player who was a perennial All-Star and voted to The NBA’s 75th anniversary team and The AthleticNBA 75 list.
DEEP
Damian Lillard on the Bucks? A deal that makes the NBA say, ‘Holy (bleep)!’
In 2020, with Antetokounmpo’s future more uncertain than what a super-maximum contract extension would be, the Bucks traded for Holiday to push the team closer to a championship. Eight months later, they secured their first NBA championship in 50 seasons with a victory over the Suns in the 2021 NBA Finals.
Three years later and with similar questions about Antetokounmpo’s future amid extension eligibility, Bucks general manager Jon Horst acquired Lillard by making the tough and emotional decision to trade Holiday , the player he traded for to help the Bucks win that title in 2021. And the move will go a long way toward securing the Greek Freak’s future again.
But it was a deal that surprised much of the NBA world. With most expectations throughout this process being that Lillard could end up in Miami and with the loudest chatter in the days leading up to the blockbuster trade that he would end up in Toronto, a deal with the Bucks seems off the radar.
Here’s how it all comes together.
From the moment Lillard requested a trade from the Blazers on July 1, he let the team know he wanted a deal specifically with the Eastern Conference champion Heat, sources said about those talks. Lillard believes he has given the Blazers loyalty for 11 seasons and wants the franchise to move him to his desired landing spot.
The Blazers and Heat had multiple conversations in July, but the sides never got down to substantive negotiations, according to those sources. In the initial call, the Blazers asked the Heat for either Jimmy Butler or Bam Adebayo. The Heat believed the Blazers had little interest in making a deal with them, and as much as Lillard and Goodwin wanted the Blazers to try to satisfy the seven-time All-Star’s wishes, Portland refused. As the summer progressed, Lillard wanted the Blazers to find a deal with Miami, but those wishes, in his mind, weren’t coming true either.
For their part, the Heat, league sources said, were prepared in July and August to offer up to three first-round draft picks — with Tyler Herro going to the third team — and multiple second-rounders and swap with expiring contracts and 2022 first-round pick Nikola Jović. But the Blazers have no interest in either side having that level of contention.
As the Blazers began serious league-wide trade talks on Sept. 18, a group of teams — the Bucks, Boston Celtics, New Orleans Pelicans, Toronto Raptors, Minnesota Timberwolves and Chicago Bulls — all expressed interest in Lillard, the league sources said The Athletic. For all involved, questions revolved around the price tag for Lillard and whether the roster could compete for a championship post-acquisition.
Meanwhile, in Lillard’s camp, sources on the matter say there is a realization that he needs to seriously consider the possibility of playing somewhere other than Miami. That’s been the case since the beginning, back in Lillard fielded a recruiting call from Jayson Tatum of the Celtics not long after his trade request.
But when Cronin stopped responding to all communications from Goodwin in mid-September — with tensions rising between the two sides along the way — sources briefed on the discussions said it inspired the agent to explore other team options that would be Lillard’s preference. And Tatum, as it turns out, isn’t the only superstar who wants to bring him to town.
Antetokounmpo is also a big fan.
DEEP
The Bucks trade for Damian Lillard signals one thing: It’s time for another championship push
Throughout this Lillard saga, there has been the looming question of whether a team would pick up his massive contract if he didn’t want to be there. Lillard has three years remaining on his deal and a player option for 2026-27 for a projected $63.2 million. For example, the Raptors’ interest was serious, but Lillard’s disinterest in playing in Toronto remained an obstacle until the end.
But once Lillard was convinced that joining the Heat was nearly impossible, sources said he became open to the possibility of playing for the Bucks and Brooklyn Nets. Backchannel blessings began. Goodwin, sources in the talks said, expressed Lillard’s interest in those teams as a way to pave the way for a possible deal. League sources say the Suns, eyed on Nurkić and other roster depth, are planning to be part of a trade with the Bucks, Nets or Heat.
The Blazers began discussing the framework of the Suns’ involvement in the Ayton-for-Nurkić swap in mid-July but needed two months to find a third team for Lillard and ensure they didn’t incur the luxury tax that Ayton was given. highest salary.
For the Trail Blazers, Phoenix is an important part of any Lillard trade. Portland values Ayton, 25, as a foundational piece to anchor a roster led by Henderson and Sharpe, and the talented big man is sure to be a 20-and-10 threat in his new home. In terms of Holiday, the league-wide expectation is that the Blazers will work hard to find the two-time All-Star a new home with several playoff contenders in the mix.
In Phoenix, Nurkić is seen as a better fit for the Suns’ style of play and culture, and his contract (three years, $54.4 million), compared to Ayton’s deal (three years, $102.1 million) gives the franchise additional flexibility moving forward a roster with three top salaries in Devin Booker, Kevin Durant and Bradley Beal.
After their lackluster finish in the Western Conference semifinals last season, indications from the Suns organization that it would be open to moving Ayton in a trade made sense — and general manager James Jones, CEO Josh Bartelstein and owner Mat Ishbia found one of the Blazers.
Milwaukee got serious last week, believing that pairing Lillard with Antetokounmpo would serve as a convincing reason for Lillard to want to join the Bucks, even if they weren’t his original preferred destination.
Now, Antetokounmpo is eligible for a three-year, $186.6 million extension with the Bucks before the start of the regular season or a commitment of up to four years and $260 million next offseason. The Bucks gave Antetokounmpo the max, three-year extension in recent days, league sources said, and it’s unclear how he and his representatives will reconsider a potential deal now versus waiting to review after the season.
Milwaukee owners Wes Edens and Jimmy Haslam showed true aggressiveness Wednesday, picking up the four years and $216 million remaining on Lillard’s contract. It went a long way to show Antetokounmpo that, yes, they want to win, too.
DEEP
How will the Heat recover from the loss of Damian Lillard? They can’t stand pat
For Lillard’s part, he’s finally getting a chance to win it all, something he’s wanted for a long time, even if the city he’s landed in isn’t exactly what he had in mind.
He has everything but one championship on his résumé. Seven All-Star appearances. Seven All-NBA selections. All those playoff memories that helped make him the best Blazers player of them all.
But this — a title-contending roster that fits his generational skill set — is what he’s always dreamed of in the City of Roses.
“In a perfect world, I could spend my entire career in Portland,” he said on a podcast earlier this month.
It’s an imperfect process, in other words, and a flawed pairing in recent years. But both sides found a way to win, just in time for the games to begin.
Related reading
Quick: After the Lillard trade, what’s left is worth celebrating
Harper: Grading the NBA’s latest megadeal
Related listening
(Photo by Amanda Loman/Getty Images)
