Milwaukee Bucks Risk Losing Damian Lillard as the Star Now Open to Joining Boston Celtics After Past Rejection…
In a surprising twist that could shake up the NBA’s Eastern Conference, Milwaukee Bucks star Damian Lillard is reportedly reconsidering his previous stance on joining the Boston Celtics—leaving the Bucks organization in an increasingly vulnerable position as the offseason heats up.
A Change of Heart
Lillard, 34, who previously showed little interest in the Celtics as a potential destination, has now expressed openness to wearing green and white. This development follows Milwaukee’s disappointing playoff exit in the second round and rising tensions surrounding roster construction and long-term competitiveness.
According to league sources, Boston was one of the few teams seriously pursuing Lillard after he was waived by the Bucks earlier this month as part of a contractual restructuring attempt gone wrong. Though Lillard eventually re-signed with the Portland Trail Blazers on a three-year, $42 million deal, reports suggest Boston’s aggressive push left a strong impression.
Tatum’s Recruitment
One of the biggest influences on Lillard’s change of heart appears to be Celtics star Jayson Tatum. Multiple sources confirm that Tatum made personal overtures to Lillard, pitching the opportunity to join an already formidable core of Tatum, Jaylen Brown, and newly re-signed guard Derrick White.
Both Tatum and Lillard are currently recovering from Achilles-related injuries, which has allowed them to connect more deeply during rehabilitation sessions and off-court conversations. This budding camaraderie has added weight to the idea that Lillard could still find his way to Boston—if not now, then perhaps later via trade or buyout.
Milwaukee’s Gamble Backfires
The Bucks’ decision to waive and attempt to renegotiate Lillard’s deal is now being criticized as a severe miscalculation. While the front office hoped to reduce salary cap pressure and retool around Giannis Antetokounmpo, the move instead created friction with one of their most consistent postseason performers.
Lillard averaged 21.7 points and 6.4 assists last season, providing a vital offensive spark alongside Antetokounmpo. His departure or potential trade would leave a significant gap in the Bucks’ rotation—especially with Khris Middleton and Brook Lopez also entering uncertain contract years.
Boston’s Rising Contenders
Meanwhile, Boston continues its rise as one of the NBA’s most attractive destinations. Fresh off an Eastern Conference Finals appearance and bolstered by key offseason moves, including the drafting of Spanish sensation Hugo González, the Celtics have both the cap flexibility and championship ambition to lure marquee talent.
If Lillard does become available again, Boston is expected to be first in line.
What’s Next?
Though Lillard’s re-signing with Portland closed the door—temporarily—on a move to Boston, league insiders believe this is far from the end of the story. The Celtics, known for their patience and shrewd asset management under President Brad Stevens, could look to revisit talks at the trade deadline or next offseason.
As it stands, Milwaukee is on high alert, knowing they’ve already tested the loyalty of one of the league’s most respected veterans. If they’re not careful, they could lose him for good—this time, to a direct rival.
Stay tuned for more updates as the Damian Lillard saga unfolds.
