Milwaukee Bucks: Damian Lillard Most Likely Headed to Powerhouse in East, League’s Best Team over Past 4 Years

Damian Lillard Has Drawn Interest from Contenders Throughout the League

Whether Lillard comes back at the end of 2025-26, and how effective he would be then, is unknown. Whoever signs him will do so to gain his services for the following season, in the hope that he returns remotely close to form. In 58 games for Milwaukee in 2024-25, he averaged 24.9 points and 7.1 assists. He will turn 36 next July.

Since the Bucks waived Lillard to clear cap space for Myles Turner, a number of suitors have been named. Despite already trading for a scoring guard this summer, the Clippers’ Norman Powell, Miami remains in the running.

ClutchPoints’ Brett Siegel also lists the Warriors and Timberwolves. A pair of previous suggested fits, the Lakers and Trail Blazers, are absent.

In addition to the above three contenders, Siegel says, the Boston Celtics have emerged as Lillard’s likeliest new team. Boston will muck through something of a gap year next season, waiting on the recovery of franchise star Jayson Tatum, who also tore his Achilles in the playoffs. Signing Dame would give them a point guard to pair with Tatum upon his return in 2026-27, when both should be healthy.

Former Milwaukee Bucks Star Would Find Good Fit in Boston

If the Celtics hold on to Jaylen Brown and Derrick White, alongside Payton Pritchard of the bench, Lillard would have a much, much smaller workload than he did in Milwaukee. Given his age and the uncertainty around his recovery, that type of setting makes a lot of sense.

Boston has finished top two in the East each of the past four seasons, winining the league’s most games in that span. They made the 2022 Finals and won it in 2024, before their strange playoff run, capped by Tatum’s injury, ended in the second round last year.

Either in the starting lineup or in the second unit, Lillard would provide a veteran threat. By ’26-27, Boston should be back in title-contending shape. If Dame indeed stays in the East, the Bucks will have a chance to face him several times in the regular season and possibly during the playoffs.

In the meantime, they’ll carry his dead money on the books until 2030 as a result of waive-and-stretching his $113 million contract.