Blazers pulled off a trade so lopsided that it's still making headlines

ESPN's Zach Kram ranked the biggest NBA roster mistakes since 2020, placing the Milwaukee Bucks' acquisition of Damian Lillard in the top tier of "Franchise-altering terrible trades," ranking it third worst overall. Only the Dallas Mavericks' trade of Luka Doncic and the Phoenix Suns' moves for Kevin Durant and Bradley Beal were deemed worse. This trade involved three teams: Portland received Jrue Holiday, Deandre Ayton, Toumani Camara, Milwaukee's 2029 unprotected first-round pick, and swap rights in 2028 and 2030; Milwaukee received Damian Lillard; Phoenix received Jusuf Nurkic, Grayson Allen, Nassir Little, and Keon Johnson.

Although Lillard preferred Miami, Portland's GM Joe Cronin accepted Milwaukee's offer because it maximized the Blazers' return while also giving Lillard a legitimate shot at a championship, pairing him with Giannis Antetokounmpo on the top-seeded Eastern Conference team. The trade seemed smart initially but failed due to lack of cohesion and poor injury timing. Statistically, the Lillard-Giannis pick-and-roll was middling (46th out of 83 combinations). Injuries plagued them, with Giannis missing the 2023-24 playoffs and Lillard missing parts of both postseasons, leading to consecutive first-round exits. Lillard's Achilles tear during the 2024-25 postseason was the final blow.

The failure forced Milwaukee to waive and stretch Lillard's contract, owing him $113 million over five years to clear cap space for Myles Turner. Surprisingly, Portland then re-signed Lillard on a team-friendly three-year, $42 million deal. This outcome significantly benefits Portland. Milwaukee's future draft picks sent to Portland increase in value due to Milwaukee's dead money limiting roster flexibility and the potential for Giannis to leave. Portland also acquired building blocks like Toumani Camara and Deni Avdija through assets gained in the initial trade and subsequent moves. Lillard's return completes a full-circle moment, confirming Cronin's bet against Milwaukee has already paid off handsomely, especially as the draft picks have yet to be conveyed.