Portland Trail Blazers fans knew it was coming, but they were still heartbroken when it became official. For the first time in 10 years, Damian Lillard wouldn't wear a Trail Blazers jersey, but instead, a Bucks one after the 2023 trade that sent him to Milwaukee.
The Trail Blazers received Jrue Holiday, Deandre Ayton, Toumani Camara, a 2029 unprotected first-round pick, and unprotected 2028 and 2029 swap rights (with the Bucks) in the three-team deal. They flipped Holiday to the Celtics for Robert Williams III, Malcolm Brogdon, a 2024 first-round pick, and an unprotected 2029 first-round pick.
Receiving Ayton didn't work out, hence why Portland bought him out earlier this summer, but all in all, the trade was a win for the Trail Blazers. Camara is a rising star, and Portland loaded up on assets.
To add another layer to the trade, the Trail Blazers traded for Holiday this summer and signed Lillard after the Bucks waived and stretched the remainder of his contract. Milwaukee didn't win a championship with its Giannis-Dame pairing, failing to make it past the first round.
Who won that trade? Portland, by a wide margin.
Blazers' Damian Lillard trade has aged better than anyone expected
Lillard will miss next season as he recovers from his Achilles injury, so the next time he plays in a game for Portland, he'll be 36. It's impossible to know what kind of player he will be upon his return, but Dame and the Trail Blazers believe that he can help lead a young team to a title.
Portland isn't the team that people thought it'd be after the Lillard trade. The Trail Blazers finished with a 36-46 record last season, three games behind the final Play-In Tournament spot. The West is daunting, but with Dame's return next season and their young talent, Portland could return to the playoffs. They'll be a team to watch this season without Dame.
The reality is that while it'd be one of the best storylines in NBA history if Lillard led the Trail Blazers to a title before retiring, the trade has already come full circle. He never really wanted to leave Portland in the first place, telling himself that he'd wear a Trail Blazers jersey again one day. He didn't think that he'd be back with the organization so soon, but here we are.
Not only did Portland get the upper hand in the deal, but Dame is back, too.