Blazers get last laugh as Bucks dumping Damian Lillard backfired

Damian Lillard has surprisingly returned to the Portland Trail Blazers after spending only two seasons with the Milwaukee Bucks. The Bucks' initial aggressive move to acquire Lillard backfired, resulting in consecutive first-round playoff exits. This offseason, Milwaukee compounded that mistake by waiving and stretching the remaining $113 million on Lillard's contract over five years to clear cap space.

Milwaukee's urgency to win now around superstar Giannis Antetokounmpo led them to sign free agent Myles Turner to a four-year, $108 million deal. However, Turner—who averaged just 10.6 points and 4.4 rebounds in the Finals—is not considered a suitable co-star for Giannis or a significant upgrade for the team. The Bucks now face limited financial flexibility due to paying substantial long-term deals to both the departed Lillard and the limited Turner.

The Portland Trail Blazers have capitalized significantly on Milwaukee's missteps. They previously acquired valuable assets in the initial Lillard trade, including players Toumani Camara and Deni Avdija, as well as Milwaukee's unprotected 2029 first-round pick and swap rights in 2028 and 2030. These draft picks are expected to gain even more value if Giannis eventually decides to leave Milwaukee.

Portland's front office, led by GM Joe Cronin, made a bold bet against the Bucks—a recent championship team with a top-five player in his prime—and that gamble is paying off. The Blazers were able to trade Lillard at peak value, use the acquired assets to shape their rebuild, and now bring Lillard back on a team-friendly deal. At 35 years old and recovering from an Achilles tear, Lillard may not be the same player, but Portland has already won the trade regardless of his on-court contributions.