With the NBA offseason calendar moving toward September and no trades in sight to his preferred trade destination in the Miami Heat, Damian Lillard reintegrated himself into the Portland Trail Blazers ecosystem. Over the past two weeks, team sources say Lillard has been working out at the Blazers’ practice facility, interacting with players and coaches.
Nearly three months after his trade request, was there a merger in progress? No, but Lillard wanted the Blazers to know he was willing to remain patient as his uncomfortable exit played out.
During a call between Lillard’s agent, Aaron Goodwin, and Blazers general manager Joe Cronin earlier this month, it was announced that Lillard would simply join Portland for training camp. Lillard has let the Blazers know he’s ready to be fully present for the start of the 2023-24 season, if only to give the organization more time to work on a potential trade with the Heat, according to sources informed of these conversations. But according to league sources, Cronin expressed skepticism about that approach. The Blazers were determined to get a deal done before camp started.
Over the next two weeks, the Blazers focused on trading Lillard before the start of training camp and media day on Oct. 2 — and suppressing speculation and what they believed to be a cloud over the organization. Cronin and his front office assembled tremendous young talent in Scoot Henderson and Shaedon Sharpe, and the Blazers were poised for a drama-free camp.
So the Blazers pulled off the long-awaited blockbuster trade on Wednesday, trading Lillard to the Milwaukee Bucks in a three-team deal that sent Jrue Holiday, Deandre Ayton, Toumani Camara, a Bucks first-round pick to 2029 and two trades of picks for the Bucks in 2028. and 2030 in Portland. Jusuf Nurkić, Nassir Little, Keon Johnson and Grayson Allen leave for Phoenix.
The trade has huge implications for the NBA landscape. The Bucks are now one of the favorites to win the 2024 championship, teaming Lillard with Giannis Antetokounmpo, Khris Middleton, Brook Lopez, NBA Sixth Man of the Year candidate Bobby Portis and shooters Pat Connaughton and Malik Beasley.
After he made public comments from being unsure about the Bucks’ desire to contend for a title and being unsure himself about signing an extension, Antetokounmpo was named an All-NBA player who is a perennial All-Star and was elected to the NBA 75th Anniversary Team And AthleticismNBA 75 roster.
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In 2020, with Antetokounmpo’s future uncertain ahead of what was a super max contract extension, the Bucks traded for Holiday to move the team closer to a championship. Eight months later, they won 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 lands Lillard by making the difficult and emotional decision to trade Holiday, the player he traded for to help the Bucks win that title in 2021. And the move could go a long way toward securing the Greek Freak’s future again.
But it was a deal that shocked much of the NBA world. With much of the expectation throughout this process being that Lillard could end up in Miami and with the loudest talk in the days leading up to the blockbuster trade being that he could go to Toronto, a deal with the Bucks seemed to be far off the radar.
Here’s how it all went down.
From the time Lillard requested a trade from the Blazers on July 1, he informed the team that he wanted a deal specifically with the Eastern Conference champion Heat, according to sources briefed on those discussions. Lillard thought he had retained the Blazers for 11 seasons and wanted the franchise to move him to its preferred landing spot.
The Blazers and Heat had several conversations in July, but the sides never engaged in substantive negotiations, according to these sources. In an initial call, the Blazers asked the Heat for Jimmy Butler or Bam Adebayo. The Heat came to believe that the Blazers had little to no interest in committing to a deal with them, and as much as Lillard and Goodwin wanted the Blazers to try to accommodate the seven-time All-Star’s wish, Portland refused. As the summer progressed, Lillard wanted the Blazers to reach a deal with Miami, but those wishes, in his mind, were also not met.
For their part, the Heat, according to league sources, were prepared in July and August to offer up to three first-round picks – with Tyler Herro joining a third team – and several second-round picks and trades as well as expiring contracts and 2022. first round pick Nikola Jović. But the Blazers were disinterested, with each side developing some level of feud.
As the Blazers began serious trade talks within the league on September 18, a slew of teams – the Bucks, Boston Celtics, New Orleans Pelicans, Toronto Raptors, Minnesota Timberwolves and Chicago Bulls — have all expressed interest in Lillard, according to league sources. said Athleticism. For everyone involved, the questions revolved around Lillard’s price tag and whether the team would be able to compete for a championship after the acquisition.
Meanwhile, in Lillard’s camp, sources briefed on the matter say there has been a realization that he should start seriously considering the prospect of playing somewhere other than Miami. This was the case all along, back when Lillard responded to a recruiting call from Celtics’ Jayson Tatum shortly after his trade request.
But when Cronin stopped responding to all communications from Goodwin in mid-September — as tension grew between the two sides along the way — sources briefed on the discussions say it inspired the agent to explore other team options that would be to Lillard’s liking. And it turns out Tatum wasn’t the only superstar who wanted to bring it to town.
Antetokounmpo was also a big fan.
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Throughout this Lillard saga, there was a question as to whether any team would take on his huge contract if he didn’t want to be there. Lillard has three years remaining on his contract plus 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.
Yet once Lillard was convinced that joining the Heat was virtually impossible, sources briefed on the discussions say he became open to the prospect of playing for the Bucks and Brooklyn Nets. The backchannel blessings have begun. Goodwin, according to sources briefed on the discussions, communicated Lillard’s interest to those teams in order to pave the way for a possible deal. League sources say the Suns, with their sights on Nurkić and other rosters, were planning to participate in trades with the Bucks, Nets or Heat.
The Blazers began discussing the scope of the Suns’ involvement in the Ayton-for-Nurkić trade in mid-July, but it took them two months to find the third team for Lillard and ensure they would not enter into the luxury tax since Ayton is present. maximum salary.
For the Trail Blazers, Phoenix was a vital part of any Lillard trade. Portland viewed Ayton, 25, as a fundamental piece to anchor a roster led by Henderson and Sharpe, and the talented big man is sure to be a 20-for-10 threat in his new home. As for the holidays, the Blazers are expected to work to find the two-time All-Star a new home with several playoff contenders right 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 (three years, $102.1 million). dollars), gives the franchise additional flexibility moving forward. a list with three maximum salaries in Devin Booker, Kevin Durant and Bradley Beal.
After their lackluster showing in the Western Conference semifinals last season, indications from the Suns organization were that it would be open to moving Ayton in a trade that made sense — and general manager James Jones, the CEO Josh Bartelstein and owner Mat Ishbia found one with the Blazers.
Milwaukee made a serious commitment over the past week, believing that pairing Lillard with Antetokounmpo would serve as a compelling factor for Lillard to want to be with the Bucks, even if they weren’t his initial 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 during next offseason. The Bucks gave Antetokounmpo the maximum three-year extension in recent days, according to league sources, and it’s not immediately clear how he and his representatives will reconsider a potential deal now rather than waiting for an evaluation after the season.
Milwaukee owners Wes Edens and Jimmy Haslam showed real aggression Wednesday, taking on the remaining four years and $216 million of Lillard’s contract. This went a long way in showing Antetokounmpo that, yes, they really want to win too.
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For his part, Lillard finally has the chance to win it all, something he’s always wanted, even if the city he landed in isn’t exactly the one he had in mind.
He has everything but a championship on his resume. Seven All-Star appearances. Seven All-NBA selections. All those playoff memories that helped make him the greatest Blazers player of them all.
But this is what he always dreamed of in the City of Roses – a roster of title contenders that fits his generational skillset so well.
“In a perfect world, I could spend my entire career in Portland,” he said on a podcast. earlier this month.
It was an imperfect process to say the least, and an imperfect match over the last few years. But both teams found a way to win, just in time for the games to begin.
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(Photo by Amanda Loman/Getty Images)