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.

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.

According to ESPN’s Shams Charania, confirmed by the Milwaukee Bucks, Damian Lillard has been diagnosed with a torn Achilles. An injury he suffered Sunday night in the first quarter against the Indiana Pacers.

This was an non-contact injury, which looked brutal from the very beginning. Lillard needed assistance to the locker room and would be ruled out for the remainder of the game; Chris Haynes was the first to report it.

During the 2023-24 postseason, the 34-year-old was dealing with an Achilles issue that forced him to miss the end of Milwaukee’s playoff run.

Per medical professionals, the typical recovery timeline for an Achilles tear is at least 12 months. There is significant speculation of him missing the entire 2025-26 season.

In this season, Lillard averaged 24.9 points, 4.7 rebounds, and 7.1 assists.

Before making his return to the court for their first round matchup against Indiana, Lillard was dealing with deep vein thrombosis – an injury that took him out for some time.

Next season, Lillard will be making $54.1 million. The following season, 2026-27, he will have a $58 million player option. If he opts in, then the veteran won’t be an unrestricted free agent until the age of 37.