In a stunning twist that has sent shockwaves across the NBA, Damian Lillard is reportedly “elated” following the Milwaukee Bucks’ decision to waive him, according to The Athletic. The move not only ends Lillard’s short and rocky tenure with the Bucks but also sets a new financial precedent, as Milwaukee will pay over $22 million per year for the next five years—making it the largest waive and stretch provision in NBA history.
Lillard’s time in Milwaukee, which began with massive expectations following his blockbuster trade from Portland in 2023, never fully clicked. While he had flashes of brilliance, the on-court fit with Giannis Antetokounmpo and the Bucks’ system felt awkward from the start. The team struggled to find a consistent rhythm, and injuries, coaching changes, and internal pressure only compounded matters. The chemistry between Lillard and the team never reached the heights many had hoped for, despite their star-studded roster.
Off the court, things were no easier. Lillard reportedly found it difficult to adjust to life away from his family, particularly his children. Known for his strong roots and deep ties to the Portland community, the move to Milwaukee represented a dramatic shift, both personally and professionally. According to sources close to Lillard, the distance from his children and the inability to find emotional balance contributed significantly to his unease in Milwaukee.
Now, Lillard enters free agency with something rare in professional sports: freedom. At 34, he may not be the same player who regularly dropped 40-point nights in Portland, but he’s still an elite shot-maker and clutch performer. With multiple contenders likely to pursue him—particularly those in warmer markets or on the West Coast—Lillard can now prioritize lifestyle, family proximity, and basketball fit over contract size or trade leverage.
For the Bucks, this is an organizational earthquake. Waiving Lillard and agreeing to stretch his remaining contract over five years means sacrificing over $22 million in cap space annually—seriously handicapping their financial flexibility for the foreseeable future. It’s a calculated risk: by cutting ties now, they gain clarity and can reshape the roster around Giannis, but they’ll carry this cap burden like an anchor unless they make additional dramatic moves.
The decision also raises larger questions about the Bucks’ long-term strategy. The Lillard-Giannis pairing was meant to signal championship urgency. Now, after a single underwhelming season, they’ve pivoted in a direction that many view as desperation—or at least resignation. Milwaukee must now retool around its franchise cornerstone without the high-end point guard they mortgaged their future to acquire just a year ago.
For Lillard, however, this may be a new beginning. “Freedom” is not a word NBA stars often get to say without the burden of optics or loyalty debates. After years of giving his all to Portland and enduring a tough stop in Milwaukee, he now controls his narrative again.
And based on early reports, he couldn’t be happier.
