Details On Damian Lillard’s “Messy” Exit From Portland

Multiple reporters have cited sources who said the Trail Blazers hadn’t discussed a Damian Lillard trade with the Heat — Lillard’s preferred landing spot — since July.

According to Chris Haynes of Bleacher Report, the last dialogue the two sides had was a phone call at Summer League between Blazers GM Joe Cronin and Heat GM Andy Elisburg. Miami wanted to set up an in-person meeting in Las Vegas to have further discussions, but it never transpired, per Haynes.

How this summer played out behind the scenes definitely left a sour taste in my mouth,” Lillard told Haynes. “But it doesn’t change the amazing experiences I’ve had with the Trail Blazers and this city. I’ll always cherish this place. This is my home. I’ll always live here regardless.”

The situation became acrimonious almost immediately, as the Blazers felt Lillard’s trade request had put them at a negotiating disadvantage, while Miami believed Portland was acting out of emotion instead of understanding the league is a business, Haynes writes.

Following a lengthy period of inactivity, Aaron Goodwin, Lillard’s agent, suggested that Cronin meet with Lillard in the event that the longtime star returned to the team.

As Haynes details, at the meeting on September 5, Lillard expressed his disappointment with the situation and wondered why there hadn’t been any communication between Portland and Miami. He didn’t want to be traded anywhere else and noted that he’d been willing to sacrifice for the team.

Specifically, Haynes cites sources who say the Blazers asked Lillard to sit out the final 10 games of last season to boost Portland’s lottery odds. Lillard was told a top pick would improve the front office’s chances of trading it for a win-now veteran. Lillard reluctantly agreed, with the team citing a “calf injury.” Portland ultimately kept the pick and selected Scoot Henderson No. 3 overall.

According to Haynes, Cronin told Lillard at the September 5 meeting that he planned to extract every possible asset from the Heat if he had to deal with them. Realizing that was unrealistic, Lillard responded by saying if he couldn’t land in Miami, he’d prefer to rescind his trade request and return to Portland.

Cronin told Lillard he couldn’t come back, which “shocked” the 33-year-old, sources tell Haynes. Lillard was “discouraged” that he couldn’t return to the Blazers, but he also didn’t want to be somewhere he wasn’t wanted, so he ended the meeting.

Shortly thereafter, the Blazers — who were frustrated with their offers at that point — refused to communicate with Lillard and Goodwin for almost three weeks. Portland didn’t want Goodwin meddling in trade talks, which is how the team rationalized the decision, per Haynes.

With Cronin refusing to talk, Goodwin came up with a contingency plan, letting both Milwaukee and Brooklyn know Lillard would be interested in joining those two teams. Haynes is now the third to report that information regarding the Bucks and Nets.

The NBA actually got involved on September 23 because of the contentious communication breakdown, Haynes writes. Cronin agreed to have dialogue with Goodwin at that point, and a few days later Lillard was traded to the Bucks.

Two-time MVP Giannis Antetokounmpo admitted he has mixed emotions about the trade, he told Haynes.

It’s a bittersweet day for the city of Milwaukee,” Antetkounmpo said. “You get Dame, who is a great player, but you lose a great guy. Jrue (Holiday) took us to the promised land. I’m 10 years in now. I know it’s a business. At the end of the day, Jrue will alway be be my brother for life. He’s one of the best human beings I’ve been around. But we’ve got to focus on the goal to win the championship. Dame wants this. He’s hungry to win, and he’s going to push us. I’m very happy to have him on our team.”

Haynes’ story for Bleacher Report has more details and quotes and is worth reading in full.

Here are some more notes related to the three-team blockbuster:

  • In a series of Twitter posts, Lillard sent a heartfelt thank you and goodbye to Blazers fans, teammates, coaches, employees, the media, and more. In conclusion, he wrote, “As this chapter of my life ends, I look back and realize how special it was. Even in this moment I feel sad that we never accomplished what I so badly wanted to. I don’t cry much, but I know my love for you is real because I am for sure dropping some tears right now. Rip City you know my heart and where I stand because I’ve stood there for over a decade so to have to move off my square hurts my heart. … I do believe a day will come where I put on a Blazers uniform on again, and hopefully by then I’ll be forgiven for breaking your hearts along with my own.”
  • Center Deandre Ayton, who was sent to Portland in the deal, also sent a thank you message to the Suns (via Twitter).
  • Only Lillard and Holiday will be required to report and pass physicals as part of the deal, according to ESPN’s Bobby Marks (Twitter links), who adds that Holiday can’t be traded until both players pass their physicals. The Blazers owe the Bulls a top-14 protected first-rounder through 2028, and if it conveys that summer, Portland’s ’28 first-round pick swap with Milwaukee will be voided, Marks reports.
  • The Blazers generated an $8.8MM traded player exception in the deal, while the Suns got a $1.1MM TPE, per Marks.
  • In another tweet, Marks notes that Holiday can’t be aggregated with other salaries for two months, though he can be traded on his own (or with one or more players if his salary isn’t aggregated with theirs).
  • While multiple reports have now said Goodwin reached out to Brooklyn, hears the Nets were never interested and only discussed Lillard with Portland one time, in July. The Nets simply didn’t believe Lillard could turn them into a contender and were wary of his age and long-term contract, per NetsDaily.
  • Yossi Gozlan of HoopsHype explores what’s next following the deal, while Sam Vecenie of The Athletic evaluates the trade for the Bucks, Blazers and Suns.
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