Milwaukee Bucks fans now face the unusual scenario of Damian Lillard and Jrue Holiday teaming up on the Portland Trailblazers, a development that has raised eyebrows given their recent history. This unlikely reunion followed Lillard’s waiver by the Bucks and was partly sparked by a simple emoji sent by Holiday, signaling a new chapter for both players.

Rather than happenstance, the alignment of Lillard and Holiday on the Blazers appears to be the outcome of moves set in motion long before the waiver, with clear intentions and subtle recruitment at play. After a recent introductory press conference, Lillard shared insights about his relationship with Holiday and the dynamics he expects within the team.

The Role of a Text and Past Connections in Lillard’s Move

During a youth basketball camp in Beaverton, Damian Lillard revealed that shortly after being waived by the Bucks, Jrue Holiday reached out with an emoji to encourage him. This gesture was more than friendly support; it symbolized Holiday’s wish to bring Lillard back to Portland. Lillard also disclosed that he had attempted to attract Holiday to the Blazers back in 2021 when Holiday moved from New Orleans to Milwaukee, suggesting a long-standing mutual interest.

Damian Lillard said today at his kids camp in Beaverton that as soon as he got waived, Jrue Holiday texted him the emoji. Also said he was trying to get Jrue to Portland in 2021 when he was traded from New Orleans to Milwaukee.
— Sean Highkin (@highkin) July 23, 2025

The deal that brought Holiday to the Trailblazers was finalized near the end of June, shortly before Lillard’s waiver became official, setting the stage for their reunion on the same team.

Why Portland Remained Lillard’s Destination of Choice

Although Jrue Holiday’s emoji and encouragement played a notable role, Lillard’s decision to return to Portland was driven by deeper, more personal motives. Insider Chris Haynes reported that Lillard specifically requested to conduct his rehabilitation in Portland, close to his family and community where he has lived since his 2012 draft. This desire to settle his rehab in a familiar environment reportedly triggered discussions that led to his release by Milwaukee.

Portland remains home for Lillard, not only in terms of geography but as the city where he built his legacy over more than a decade as a leading figure for the Trailblazers. The strong ties to the community and a sense of belonging influenced his preference to come back.

From a financial perspective, the Bucks gained relief from Lillard’s contract by waiving him, stretching out the remaining salary over five years instead of two, which reduced their salary cap hit to $20 million for the current season from $56 million. This maneuver allowed Milwaukee to bring in Myles Turner, a promising young talent to support Giannis Antetokounmpo in their backcourt rotation.

Looking Ahead: The Future of the Blazers with Lillard and Holiday

Both Lillard and Holiday are anticipated to make a strong impact with the Trailblazers, although Lillard’s return to the hardwood will be postponed as he focuses on recovering from a torn Achilles injury with a full rehab dedication for the 2025-26 season. Despite this, he expressed enthusiasm about teaming up with Holiday when healthy, signaling optimism for the team’s prospects.

This collaboration marks a meaningful moment for Portland fans, signaling the return of their former superstar alongside a talented new teammate with whom Lillard shares history and mutual respect. Their joint presence could reshape the Blazers’ trajectory in the coming seasons, promising renewed energy and leadership.

Our Reader’s Queries

Q. What surgery did Damian Lillard have?

A. Today, Damian Lillard had a surgery in Los Angeles to fix a torn Achilles tendon in his left leg. Dr. Neal ElAttrache did the surgery with advice from Dr. Carole Vetter, who is the orthopaedic surgeon for the Bucks.

Q. What does Damian Lillard have tattooed on his arm?

A. After surgery for his torn Achilles, Jayson Tatum will encounter both mental and physical challenges while recovering. Tatum injured his right Achilles tendon during the Celtics’ semifinals loss to the New York Knicks. This injury significantly impacted Boston’s short-term plans.