According to Shams Charania of ESPN, the Portland Trail Blazers have signed Damian Lillard to a three-year, $42 million contract, effectively putting a cap on the Milwaukee Bucks' trade from two years ago and rendering it a complete and utter disaster. The two years of Lillard in Milwaukee could not have gone much worse.
When Lillard first joined the Bucks, Milwaukee envisioned a beautiful pairing with him and Giannis Antetokounmpo. One that could have led to more championships. Instead, they endured two first-round exits (both at the hands of the Indiana Pacers) and ended up waiving and stretching Lillard’s contract.
Meanwhile, the Blazers just got him back on a cheaper deal than they would have otherwise been paying him.
Full details of Bucks trade for Damian Lillard
The original trade that sent Lillard to the Trail Blazers involved the Bucks sending out a massive package of players and draft assets. It was a three-team trade that also included the Phoenix Suns.
Milwaukee got Lillard, but the Blazers got a ton of talent. Portland received Jrue Holiday, Deandre Ayton, Toumani Camara, the Bucks’ 2029 first-round pick, and Bucks first-round pick swaps in 2028 and 2030.
Lillard joined the Bucks on a max contract, but after two years of disappointing exits, they waived and stretched his deal, taking on roughly $22.5 million in dead money on their books for each of the next five seasons.
Effectively, the Blazers traded Lillard, got back a ton of valuable assets, and they re-signed him for a fraction of the price they would have paid him had he simply stuck around in Portland.
As for the Bucks, they basically traded all of their future draft flexibility, a ton of financial flexibility, and Holiday (who went on to help their conference rival, the Boston Celtics, win a championship) for two years of Lillard that didn’t amount to anything.
Meanwhile, the Blazers still ended up with Lillard and Holiday, who they originally flipped to Boston for Robert Williams III, draft picks, and Malcolm Brogdon, who was subsequently flipped to the Washington Wizards in a deal for Deni Avdija.
Two years after the Lillard trade was made, the Bucks are in an extremely brutal position. Lillard didn’t work out next to Antetokounmpo, and he ended up going back to the very team they made a trade with.
The full details of the Bucks-Lillard trade are incredible for Portland. And unfortunately, they make the Bucks look foolish. Milwaukee gave up a ton of assets at the time, putting a ton of pressure on Lillard to succeed on the Bucks. They sacrificed their future for Lillard. And it didn't work.
Hindsight is 20/20, but in this case, that vision reveals a terribly ugly picture.