The Portland Trail Blazers have completed part two of the Damian Lillard trade by dealing Jrue Holiday to the Boston Celtics. Holiday came to the Blazers as part of the three-team trade that sent Lillard to the Milwaukee Bucks and Deandre Ayton to Portland from the Phoenix Suns, among other pieces.
The Celtics are trading Robert Williams, Malcolm Brogdon, 2024 GSW 1st, 2029 unprotected BOS first to the Blazers, sources tell ESPN. https://t.co/gx53jyH1RG
— Adrian Wojnarowski (@wojespn) October 1, 2023
Portland Trail Blazers trade Jrue Holiday to Boston Celtics for players, picks
Holiday wasn’t expected to stay in Portland for long as the Trail Blazers are preparing to build around the young backcourt trio of Scoot Henderson, Shaedon Sharpe and Anfernee Simons. Holiday would’ve been a positive veteran presence, but would have taken significant developmental minutes away from Portland’s future core.
Instead, Blazers General Manager Joe Cronin added to the haul he received for Lillard by flipping Holiday to Boston. What did Portland get in return, and was it worth it?

Trail Blazers get Celtics’ Robert Williams III as centerpiece of Jrue Holiday trade
Portland added two more first-round picks to the one it got from Milwaukee, along with Williams and guard Malcolm Brogdon.
Cronin could end up flipping Brogdon in a similar way he did Holiday, as the 30-year-old former Rookie of the Year would siphon minutes from Scoot, Sharpe and Simons, as well.
Williams is the centerpiece of the deal from a player perspective. When healthy, the former Texas A&M standout is one of the best rim-protectors in the NBA. The 25-year-old has averaged 1.7 blocks per season during his five years in the league.
When he started 61 games for the Celtics in 2021-22, he swatted away 2.2 shots a night.
The most significant issue surrounding Williams is his injury history. Throughout his career, he’s dealt with knee, hamstring, ankle, hip and back problems, among others.
If healthy, though, Williams could pair with Ayton to create a versatile frontcourt. Ayton’s more skilled offensively, while Williams is an explosive shot blocker and rebounder. Both are good fits as pick-and-roll partners and lob threats alongside Henderson and/or Simons.
Two more first-round picks – one unprotected in 2029 and one lightly protected this year – add to the Blazers’ staple of future assets that include Milwaukee’s 2029 unprotected first and potential pick swaps in 2028 and 2030.

What grade do the Portland Trail Blazers deserve for the Jrue Holiday trade?
Portland’s grade on the Lillard trade was incomplete as we waited to see what Cronin could pull in for Holiday. To a certain extent, this trade could be considered incomplete as well while we wait to see what happens with Brogdon.
He won’t fetch the same kind of return Holiday did, though, so it’s easier to picture a complete package. Assuming Brogdon is worth another pick or possibly two, the complete Holiday trade is solid for the Blazers.
Pairing Ayton and Williams together finally solves a long-standing big man problem in Portland, both are 25, and both have the skill sets to complement the Blazers foundation as it grows.
Adding a few more first-round picks into the deal, even if the Warriors’ pick ends up in the back half of the first round this year, only adds to the Blazers assets.

