Inside the Damian Lillard trade to Milwaukee and how it came together

As the NBA offseason calendar shifted to September and there was no trade in sight to his preferred trade destination of the Miami Heat, Damian Lillard incorporated himself back into the Portland Trail Blazers’ ecosystem. For the last 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 reconciliation in the works? No, but Lillard wanted the Blazers to know he was willing to remain patient while his uncomfortable exit played out.

On a call between Lillard’s agent, Aaron Goodwin, and Blazers general manager Joe Cronin earlier this month, it was communicated that Lillard would be content rejoining Portland for training camp. Lillard let the Blazers know he was willing to be fully present 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 briefed on those conversations say. But according to league sources, Cronin expressed skepticism about that approach. The Blazers were determined to get a deal done before the start of camp.

Over the next two weeks, the Blazers’ focus turned toward trading Lillard before the start of training camp and media day on Oct. 2 — and removing the speculation and what they believed was a cloud over the organization. Cronin and his front office have amassed tremendous young talent in Scoot Henderson and Shaedon Sharpe, and the Blazers were ready for a drama-free camp.

So the Blazers made the much-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 2029 first-round Bucks pick and two Bucks pick swaps in 2028 and 2030 to Portland. Jusuf Nurkić, Nassir Little, Keon Johnson and Grayson Allen are off to Phoenix.

The trade has massive implications for the landscape of the NBA. 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 about being unsure about the Bucks’ desires to contend for a title and being unsure himself of signing an extension, Antetokounmpo has been delivered an All-NBA player who is a perennial All-Star and was voted onto the NBA’s 75th-anniversary team and The Athletic’s NBA 75 list.

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In 2020, with Antetokounmpo’s future uncertain ahead of what was a super-maximum contract extension, 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 lands Lillard by making the tough and emotional decision to trade Holiday, the player for whom he traded to help the Bucks secure that title in 2021. And the move could go a long way in securing the future of the Greek Freak once again.

But this 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 chatter in the days before 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 came together.

From the moment Lillard requested a trade from the Blazers on July 1, he informed the team that he wanted a deal specifically to the Eastern Conference champion Heat, sources briefed on those talks say. Lillard believed he gave the Blazers loyalty over 11 seasons and wanted the franchise to move him to his preferred landing spot.

The Blazers and Heat had multiple conversations in July, but the sides never engaged in substantive negotiations, according to those 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 engaging in a deal with them, and as much as Lillard and Goodwin wished that the Blazers would attempt to satisfy the seven-time All-Star’s wish, Portland refused. As the summer progressed, Lillard wanted the Blazers to find a deal with Miami, but those wishes, in his mind, also went unfulfilled.

For their part, the Heat, league sources say, were prepared in July and August to offer up to three first-round draft picks — with Tyler Herro going to a third team — and multiple second-rounders and swaps along with expiring contracts and 2022 first-round pick Nikola Jović. But the Blazers were disinterested with each side developing a level of contentiousness.

As the Blazers began to start serious trade talks across the league on Sept. 18, a bevy of teams — the Bucks, Boston Celtics, New Orleans Pelicans, Toronto Raptors, Minnesota Timberwolves and Chicago Bulls — all showed interest in Lillard, league sources have told The Athletic. For all involved, the questions revolved around the price tag for Lillard and whether the roster would be able to compete for a championship post-acquisition.

Meanwhile, in Lillard’s camp, sources briefed on the matter say there was a realization that he would need to start seriously considering the prospect of playing somewhere other than Miami. That had been the case since the start, back when Lillard fielded a recruiting call from the Celtics’ Jayson Tatum not long after his trade request.

But when Cronin stopped responding to all communication from Goodwin in mid-September — with the tension rising between both 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 Tatum, as it turned out, was hardly the only superstar who wanted to bring him to town.

Antetokounmpo also was a big fan.

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Bucks trade for Damian Lillard signals one thing: It’s time for another championship push

Throughout this Lillard saga, there was the looming question of whether a team would take on his massive contract if he didn’t want to be there. Lillard has three years remaining on his deal 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 discussions say he became open to the prospect of playing for the Bucks and the Brooklyn Nets. The backchannel blessings commenced. Goodwin, sources briefed on the talks say, communicated Lillard’s interest to those teams as a way of paving the way for a possible deal. League sources say the Suns, with their sights set on Nurkić and other roster depth, were planning to be a part of trades with the Bucks, Nets or Heat.

The Blazers began discussing the framework of the Suns’ involvement with the Ayton-for-Nurkić swap in mid-July but needed two months to find the third team for Lillard and ensure that they wouldn’t be entering the luxury tax given Ayton is on a max salary.

For the Trail Blazers, Phoenix was an essential component of any Lillard trade. Portland valued Ayton, 25, as a foundational piece to anchor a roster headed 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 expectation around the league is that the Blazers will work on finding the two-time All-Star a new home with several playoff contenders squarely 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 on a roster with three max 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 were that it would be open to moving Ayton in a trade that made sense — and general manager James Jones, CEO Josh Bartelstein and owner Mat Ishbia found one with the Blazers.

Milwaukee became seriously engaged over the last week, believing that pairing Lillard with Antetokounmpo would serve as a convincing factor for Lillard to want to be with the Bucks, even though 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 for up to four years and $260 million next offseason. The Bucks delivered the max, three-year extension to Antetokounmpo in recent days, league sources say, and it is immediately unclear how he and his representatives will reconsider a potential deal now versus waiting to evaluate after the season.

Milwaukee owners Wes Edens and Jimmy Haslam showed genuine aggressiveness Wednesday, taking on the four years and $216 million remaining on Lillard’s contract. It went a long way toward showing Antetokounmpo that, yes, they want to win badly too.

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For Lillard’s part, he finally gets the chance to win it all, something he has always wanted, even if the city where he landed isn’t exactly what he had in mind.

He has everything but a championship on his résumé. 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 — a title-contending roster that fits so well with his generational skill set — is what he 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.

This was an imperfect process, to say the least, and a flawed pairing in these recent years. But both sides found a way to win, just in time for the games to begin.

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(Photo by Amanda Loman / Getty Images)