Damian Lillard is back where it all began—and this time, it’s on his own terms. While many expected him to be heartbroken after his abrupt Milwaukee exit, the move has turned into a quiet blessing. With the Bucks still on the hook for $112.6 million over the next five years thanks to the waive-and-stretch provision, Lillard has the rare luxury of time—time to recover from his Achilles injury, and more importantly, time with his family in Portland. But as Dame settles back into familiar surroundings, one of his former Trail Blazers teammates is heading the other way, gearing up for a brand new chapter.

Jabari Walker, who was Dame’s rookie during the 2022-23 season, is moving out of Portland after inking a two-way contract with the Sixers. Bidding farewell to his first home in the NBA, Walker penned a heartfelt message on Instagram, “Thank you for three of the most meaningful years of my life. You all took a chance on a young kid from Inglewood California and gave me an opportunity to live out a dream that I’ve held since I picked up a basketball.” As the forward thanked his coaches and teammates, along with the entire Rip City, Lillard wished him well for the new chapter in his young NBA career.

Dame shared Walker’s post on his IG story, writing, “Keep goin Bari.” Highlighting his wholesome message was a picture of Lillard mentoring a young Jabari during his rookie season.

Well, Walker’s run in Portland was promising, as he averaged 6.2 points and nearly five boards during his three-year tenure. But he was limited to playing only sixty games this season due to lingering injury woes. Moreover, it also impacted his performance, as Jabari’s numbers dropped to 5.2 points and less than four rebounds. Despite a disappointing final season in Portland, the forward is excited for what’s next. “PHILLY, WHAT UP! I’m here, I’m hungry, and I’m ready to get to work. Let’s get it @sixers.” He wrote. And he received complete support from his veteran leader Dame despite his personal turmoil.

Veteran insider claims Damian Lillard’s desire for Portland return could have fuelled Bucks’ waiver

Of course, a major reason Bucks waived Lillard was that he was set to miss majority of next season recovering from his Achilles injury. But the desire to spend his rehab period in Portland with his family might also have played a part in the organization’s abrupt decision.

Giannis Antetokounmpo was noticeably shaken by the Bucks’ abrupt decision to waive Damian Lillard, his cryptic social media post—“I don’t know what’s going on right now”—hinting at frustration and uncertainty about the team’s direction.

Per veteran insider Chris Haynes, “Aaron Goodwin, Damian Lillard’s agent about a month ago reached out to the Bucks and informed them that Dame would like to rehab back home in Portland and stay with his kids… and I was told that some people within the Bucks did not approve of that.”

He continued, “I think that might have gotten the ball rolling or at least put some ideas in the heads of the Milwaukee Bucks that kind of led to this decision.” Maybe Bucks were not pleased with the idea of Lillard spending his lengthy hiatus away from the team. Whatever the reason, the waiver has seemingly opened several new doors for the Top 75 player.

While Damian Lillard continues his recovery from a torn Achilles, the interest surrounding him this offseason is heating up. Prior to the injury, Lillard was still producing at an elite level—averaging 24.9 points and over seven assists per game during the regular season. His shot-making, leadership, and big-game experience make him a highly attractive option for teams seeking a proven difference-maker.

What makes the situation even more compelling is the financial context. Because of the Bucks’ decision to utilize the waive-and-stretch provision, Lillard is still owed over $112 million—spread across the next five years—which significantly reduces any immediate financial burden for a potential suitor. That essentially frees Dame to sign with a contender without the usual cap-related roadblocks.

Now, for the first time in years, Lillard has a legitimate opportunity to pick his situation—possibly joining a ready-made contender—without being shackled by either trade demands or contract concerns. With his resume and the current playoff landscape, expect multiple franchises to circle closely, hoping to land a superstar talent at a rare discount.

Which team do you think suits him best?