Ugly Damian Lillard-Blazers divorce may have broken NBA rules

When the Trail Blazers traded All-Star guard Damian Lillard Wednesday to the Milwaukee Bucks, it closed the door on the once-promising relationship in Portland that ended with a messy divorce.

Bleacher Report’s Chris Haynes constructed the timeline for how the eight-player, three-team deal came to fruition.

After receiving his ticket out of town, Lillard wasn’t exactly jumping for joy, telling Haynes, “How this summer played out behind the scenes definitely left a sour taste in my mouth.”

Lillard requested a trade on July 1 after the team selected point guard Scoot Henderson with the No. 3 pick overall in the 2023 NBA Draft.

Lillard, 33, publicly declared his desire to be traded to the Heat.

But the last time Trail Blazers general manager Joe Cronin and Heat senior vice president of basketball operations and general manager Andy Elisburg talked was at the Summer League in July.

All along, Cronin said he would take the best deal on the table, even if it didn’t come from Miami.

The Trail Blazers traded Damian Lillard to the Bucks on Wednesday.
Portland GM Joe Cronin orchestrated the three-team, eight-player deal involving Lillard.

However Aaron Goodwin, Lillard’s agent, said the seven-time All-Star would be unhappy if South Beach wasn’t his final destination.

That led to a warning from the NBA on July 29 threatening discipline if Lillard or his agent continued interfering with Portland’s trade talks.

In late August, with no deal forthcoming, Goodwin suggested a meeting with Cronin to “mend the relationship” in case Portland doesn’t trade Lillard.

Lillard requested a trade days after Portland drafted point guard Scoot Henderson (00).

On Sept. 5, Haynes reported Cronin met with Lillard in his Portland home for about an hour.

During that meeting, Lillard shared his disappointment with how his situation was unfolding and “how it would be disheartening to be sent somewhere against his wishes.”

Lillard also referenced how he had been a good soldier for the organization during his NBA career.

Lillard was a seven-time All-Star for the Trail Blazers.

According to Haynes, “Portland had asked Lillard to sit out the final 10 games of the 2022-23 regular season to help the franchise improve its lottery odds.

“He was told the higher the draft pick, the better chance they had at using the pick to facilitate a trade for a proven veteran player. He reluctantly acquiesced to being shut down, citing a ‘calf injury.’”

If that is true, reports Portland “reportedly committed a major NBA rules violation. … A report like that is enough for the league to open an investigation into the Blazers for allegedly fabricating a calf injury for Lillard.”

As for the stalemate, Cronin made it clear he was looking for the best deal possible.

At that point, Lillard said if he can’t go to the Heat, he wanted to rescind his trade request, to which Cronin replied “there was no coming back,” per Haynes.

Lillard publicly stated he wanted to be traded to the Heat.

Starting on Sept. 11, Lillard started working out at the Trail Blazers’ practice facility and said Cronin never made an effort to talk.

As the situation devolved, Goodwin met with Lillard on Sept. 17 and came up with a “contingency plan,” Haynes wrote.

Among the “viable options” was Milwaukee.

Lillard will team with two-time NBA MVP Giannis Antetokounmpo in Milwaukee, making the Bucks a title contender.

Meanwhile, the Trail Blazers stopped communicating with Lillard and Goodwin, as calls and texts went unanswered for three weeks, forcing the league to step in on Sept. 23 for a Zoom designed to get the two sides talking.

According to Haynes, “The session got volatile at certain junctures, with both sides expressing their trust issues with the other.”

However Cronin and Goodwin started communicating again.

Four days later, Lillard was on his way to Milwaukee.