According to ESPN’s Jamal Collier, Damian Lillard has always had the plans of making a return to the Portland Trail Blazers before his retirement.

Even before being traded to the Milwaukee Bucks, he reportedly told people his plan of making a return to Portland.

“In just two years, I probably wouldn’t have believed it,” Lillard said in late July at his introductory news conference. “I’d be lying if I said I didn’t expect this to happen at some point, but for it to happen this soon, I wasn’t expecting this.”

Ultimately, his plan of returning home was sped up due to his Achilles tear. Once that happened and the Bucks no longer wanted him, Lillard was ready to return to Portland and enact his plan.

By the time Lillard is able to rejoin the Blazers, he will be 36 years old when he is fully healed from his Achilles injury.

According to multiple reports, spearheaded by ESPN’s Shams Charania, the situation with Giannis Antetokounmpo and his future with the team remains uncertain.

“Sources tell me there’s still nothing set in stone about whether Giannis Antetokounmpo will stay in Milwaukee, or whether he will be leaving,” said Charania. “And so he’s continuing to evaluate his future. I reported it in mid May that he’s evaluating whether his best fit is in Milwaukee, or is it elsewhere? And that process is continuing.

‘”There’s been some very real conversations over the last week or so. The constant question that Giannis has, though, is: ‘Can I win a championship with this roster? Is this roster going to be the one for this upcoming year and 2026-27?’ He wants to win a second championship. So he’s asking that question over and over. There are multiple teams waiting in the wings, potentially, if Giannis this offseason still makes that decision.”

His future has been unstable since the team lost in the postseason and during their attempt of trying to reshape the roster to compete for a championship.

It’s unclear when he will make a decision about his future, but, for now, it remains very unstable without a clear ending.

In a complete turn of events involving the Milwaukee Bucks and Damian Lillard, and Lillard no longer being with the team, there are no hard feelings mutually. In fact, the veteran guard is happy he was stretched and waived by the organization.

Milwaukee will owe Lillard $22 million per season for the next five years, as the money they were able to save by doing that allowed them to sign former Indiana Pacers center Myles Turner. Turner signed with Milwaukee after Indiana did not want to go into the luxury tax for him.

According to The Athletic’s Sam Amick, the 34-year-old is “elated” by the fact Milwaukee wanted him gone. Back in 2023, Lillard wanted to go to Miami instead of Milwaukee, but the Portland Trail Blazers did not want to accommodate his request to the Heat.

For the first time in his career, Lillard will have the chance to pick any team that he wants to join. Multiple reports are saying he’ll take a minimum contract so that he can have tons of options.

Per Chris Haynes, a team to keep an eye on are the Heat. Both sides have mutual interest and could see a deal get done, despite the veteran’s age and recent Achilles tear injury.

Even if Lillard did not suffer that devastating injury, the Bucks would have still discussed a potential exit for Lillard. Between the on-court fit issues and him missing his children, Milwaukee was no longer a place that made sense for either side.