Trail Blazers Trade Jrue Holiday to Celtics for Malcolm Brogdon, Robert Williams III, Two First-Round Picks

The other shoe has dropped on the Damian Lillard trade.

The grade on the Damian Lillard trade was going to be an “incomplete” until the Trail Blazers decided what to do with Jrue Holiday. Three days after the deal went through, and one day before the start of training camp, that shoe has dropped. Portland has agreed to send Holiday to Boston for guard Malcolm Brogdon, center Robert Williams III, the Warriors’ 2024 first-round pick and the Celtics’ 2029 first-round pick, a league source confirmed. The deal was first reported by ESPN.

That brings Portland’s total return on the Lillard trade to:

• Deandre Ayton

• Malcolm Brogdon

• Robert Williams III

• Toumani Camara

• 2024 first-round pick from Golden State (top-4 protected in 2024, top-1 protected in 2025, unprotected in 2026)

• 2028 first-round pick swap with Milwaukee (unprotected)

• 2029 first-round pick from Milwaukee (unprotected)

• 2029 first-round pick from Boston (unprotected)

• 2030 first-round pick swap with Milwaukee (unprotected)

Given the challenges presented to Portland’s front office by Lillard’s representation doing everything they could to limit the market to Miami and only Miami, Joe Cronin did well. The return for Holiday—two good rotation players and two first-round picks—is certainly more than Tyler Herro would have gotten on the trade market. It’s now no longer possible for anyone to claim they took a lesser deal than the hypothetical Heat package that was never actually offered.

With Scoot Henderson, Shaedon Sharpe and Anfernee Simons firmly set as Portland’s guard rotation, don’t be surprised if the Blazers take calls from contending teams on Brogdon at some point, although it’s not as urgent to move him before the season as it was to move Holiday.

An hour before the trade was agreed to, I published a training-camp preview with five storylines to watch. One of those five storylines—who will be Ayton’s backup at center—is immediately out of date with the arrival of Williams, who made second team All-Defense in 2021-22 and fits the rebuilding timeline at age 25.

The question with Williams throughout his career, and the reason he’s making mid-level money at his position and age, is his ability to stay on the floor. His injury history is extensive, and he’s only played 60 or more games in a season once, in 2021-22. With the Blazers not looking to contend in the immediate future, that isn’t as much of an urgent matter as it was for a title-or-bust team like the Celtics. Holiday will help them and is the best they could have hoped for as a Marcus Smart replacement.

As for the picks, there’s a good chance Boston’s 2029 first-rounder isn’t that good. Jaylen Brown and Jayson Tatum are just entering their primes and there’s no reason to believe the Celtics will stop contending anytime in the next decade, at least as it sits right now. The picks with the highest upside are the end-of-decade pick and two swaps with the Bucks. The Blazers are making the bet that Lillard will have aged out by then. Brook Lopez will definitely be out of the picture. Khris Middleton likely will too. And Milwaukee isn’t Miami, which is always a threat to land stars in free agency.

The 2024 Warriors pick is sneakily valuable. Just yesterday, it was reported that Draymond Green suffered an ankle injury that could keep him out the first month of the regular season. They’ll have to figure out how to integrate Chris Paul, whether to start him or bring him off the bench. Stephen Curry and Klay Thompson are a year older and have dealt with plenty of injuries in recent years. Their depth beyond their stars is suspect. Nobody expects Golden State to be a lottery team, but they were the sixth seed last season and had the No. 19 overall pick. It’s not outside the realm of possibility they land in that range again.

The Blazers wanted all of this business done before training camp, and they made it just under the wire. The team will hold media day on Monday morning at 9 a.m. before traveling to Santa Barbara for the rest of the week to hold camp on the UCSB campus.