The Milwaukee Bucks' decision to waive and stretch Damian Lillard to clear space to sign Myles Turner was ranked as the worst move since the offseason by ESPN's Zach Kram. Fortunately, the Portland Trail Blazers are now in a prime position to benefit twice from Milwaukee's desperate move that backfired.
Portland's trade has now come full circle. Not only do they get Lillard back on a team-friendly deal, but they also get the assets received from trading him away in the first place. That includes the Bucks' future draft capital -- a first-round pick in 2029 and first-round pick swaps in 2028 and 2030 -- which has suddenly become as valuable as ever.
Bucks' Damian Lillard mistake looks worse than ever
We just got a glimpse of how bad this Bucks roster is without Giannis Antetokounmpo, as Portland blew out Milwaukee in a lopsided 130-99 victory. As Kram notes, they have few avenues to upgrade their roster around Giannis because of that decision to stretch Lillard. He's still on the books for $22.5 million annually through the 2029-30 season.
The Lillard blockbuster was already viewed as a major win for Joe Cronin and Portland. They secured significant assets to help jump-start their rebuild, including a building block in Toumani Camara. In part because of those pieces, they were able to get Lillard back in Portland, citing his reason to return as a "basketball decision."
It's easy to see why, as the Blazers finally have the supporting cast to give him a legitimate shot at contention, something they lacked during his previous stint. But now that the Bucks are digging themselves a deeper hole, the Blazers have a golden opportunity to continue adding to that supporting cast in the coming seasons.
Lillard trade could singlehandedly get Portland back to contention
For context, that 2029 Bucks first-rounder was considered the second most valuable traded pick by CBS Sports' Sam Quinn back in August. Only the New Orleans Pelicans 2026 first-round pick was ranked higher. That was even before this whole Giannis trade deadline saga, and seeing that bringing in Turner would be a franchise-altering mistake.
We always knew Lillard would be back in Portland at some point in his career. He even said as such. But no one expected it to be just two seasons after trading him away. This entire Lillard-Bucks connection is singlehandedly elevating the Blazers' rebuild, and it could be the very thing that ultimately propels them to that tier of legitimate contenders.
Portland's rebuild is already in great shape. And the best part is, they still have chips waiting to be cashed in, between those future picks and Lillard's return to action next season -- all thanks to the Bucks' desperate attempt to keep Giannis around.