Where the Portland Trail Blazers went wrong in the Damian Lillard trade

The Portland Trail Blazers, coming off of a 33-49 record in the 2022-23 NBA season, had a difficult decision after landing the No. 3 overall pick in the 2023 NBA Draft. Had they gotten the No. 1 overall pick, they could have just selected Victor Wembanyama, and Lillard likely would have been content staying. Instead, they missed out on the No. 1 overall pick by one ping pong ball.

The rest is history, as the Blazers drafted Lillard's successor in G League Ignite point guard Scoot Henderson. They were better than their 33-win record indicated, as they shut down superstar Damian Lillard for the remainder of the season to improve their draft lottery odds in an attempt to land Wembanyama.

But their roster wasn't good enough to make a playoff run in the West. In that sense, the Blazers were right in choosing Henderson and the rebuilding route over trying to win now with Lillard and sacrificing their future, likely to get bounced in the playoffs anyway.

Revisiting the blockbuster Damian Lillard trade

The Bucks trade wasn't as bad as some have made it out to be. The Blazers received solid value between Team USA guard Jrue Holiday, a 2029 1st-round pick (via Bucks), and two first-round pick swaps (via Bucks in 2028 and 2030). Toumani Camara was a steal, too, coming over from the Suns.

Hopefully, the Blazers can flip Deandre Ayton at some point. However, his massive contract (owed $34 million next season and $35.6 million in 2025-26) makes him much less valuable in a potential deal. Portland should have pursued other alternatives to Ayton, but that's not the primary reason the trade hasn't worked out in their favor so far.

Why was Portland so willing to give Jrue Holiday away?

Where the Blazers and general manager Joe Cronin went wrong was their subsequent deal with the Celtics. Portland flipped Jrue Holiday for Malcolm Brogdon, Robert Williams III, the Warriors' 2024 first-round pick (turned into No. 14 overall pick, Bub Carrington), and a 2029 unprotected 1st-round pick (via Celtics).

They essentially traded NBA All-Star Jrue Holiday, a key member of both the Celtics' championship run and Team USA's gold medal run, for Williams and Deni Avdija. Avdija is a great addition, but he's not on the same tier of player as Holiday.

Blazers have no significant draft capital to show

They should have immediately flipped Williams for other assets if they were acquiring Ayton from the Suns, given RW3's injury history. Instead, their gamble on Williams backfired, and now they are stuck with four centers - one who is the highest-paid player on their roster and one who has only played more than 35 games in two of his six seasons. Neither Ayton nor Williams seem to have significant trade value because of these glaring problems.

If Portland can flip one or both of them for more draft capital, the Lillard return may look better. But they find themselves with no All-Stars or significant draft capital after trading away an NBA 75th Anniversary Team member in Lillard. Their lack of emphasis on draft capital, unnecessary rush to flip Holiday to the Celtics, and decision to hold onto Williams are primarily to blame.