The Portland Trail Blazers just went through perhaps the most trying offseason in the organization’s history. They traded franchise centerpiece and beloved superstar Damian Lillard to the Milwaukee Bucks. They landed the No. 3 overall pick in the draft and selected a potential mega-star and possible Lillard replacement in Scoot Henderson.
There were other trades as well, including flipping Jrue Holiday to the Boston Celtics. Portland collected valuable future draft picks and made additional moves in free agency.
The 2023-24 Blazers roster looks dramatically different than what head coach Chauncey Billups had at his disposal at any point last season. But did all these offseason decisions make sense? Is the team better prepared for the future? How did Portland General Manager Joe Cronin do this offseason?
Grading the most significant moves of the Portland Trail Blazers offseason
The Lillard and Holiday trades were two of the franchise-altering moves the Blazers made this summer, but as a sort of honorable mention category, here’s a list of the slew of smaller transactions Portland made:
- Drafted Kris Murray with No. 23 pick
- Drafted Rayan Rupert with No. 43 pick
- Signed C Ibou Badji and F John Butler Jr. to two-way contracts
- Signed C Moses Brown
- Signed G Skylar Mays
- Signed F/C George Conditt
- Waived Antoine Davis, Malachi Smith, Jeenathan Williams
1. Drafting Scoot Henderson
Murray and Rupert should be mentioned in any Trail Blazers 2023 NBA Draft discussion, but Scoot Henderson is a game-changer for the franchise in multiple ways. On a down note, the selection of Henderson may have put the final crack in Damian Lillard’s fractured relationship with the organization. On the flip side, by almost all accounts, Scoot projects to be a Rookie of the Year candidate and a future NBA superstar.
He’s fast, explosive, strong, can finish at the rim and has surprised coaches and players with his basketball IQ and ability to run an offense at 19 years old.
The biggest question surrounding Henderson during the draft process was his shooting. At least through three preseason games he’s changed that narrative, shooting nearly 36 percent from three on 4.7 attempts per game, and he has the work ethic to get better.
He also has the charisma and off-court presence an NBA team needs from its centerpiece.
Scoot looked like a can’t-miss prospect leading up to the draft and has only solidified that forecast during his first offseason and preseason in the NBA. He’s checked off so many boxes in fewer than four months and seems so advanced both on and off the court that it’s already becoming easy to forget he’s 19.
Blazers grade: A+
2. Re-signing Jerami Grant
Jerami Grant had his most efficient offensive season as a pro last year playing alongside Lillard and Anfernee Simons.
Grant spent two seasons with the Detroit Pistons as the team’s primary offensive weapon and understandably had his best statistical years in the Motor City, but he settled into a more suitable role with the Blazers. The 29-year-old averaged 20.5 points and shot 47.5 percent from the floor in 2022-23 and hit more than 40 percent of his threes for the first time in his 10 NBA seasons.
Jerami’s impending free agency was a major topic of conversation toward the end of last season, and it continued into the summer. Portland knew it would have to overspend to keep him, and if the goal was to keep Lillard happy, bringing one of the team’s best veteran players back seemed to be a logical move.
The Trail Blazers decided to re-sign Grant either way and will now be shelling out $160 million over the next five seasons. Is he worth that kind of money? No, not really, but he will be a serviceable player and one of the quiet leaders for a young Portland team in 2023-24.
There’s always the possibility that Grant is traded at some point, but for now, he’ll slot in as a guaranteed starter and will be expected to have another solid offensive campaign.
Blazers grade: B-
3. Retaining Matisse Thybulle
Matisse Thybulle has long been one of the best perimeter defenders in the NBA. He’ll be a significant contributor to the Blazers on that end of the floor in 2023-24.
But Thybulle also had the best offensive stretch of his career once he arrived in Portland in a deadline-day trade with the Philadelphia 76ers last year. The 6-foot-5 26-year-old shot a career-high 38.8 percent from three on a career-high 3.9 attempts per game during his 22 games in Rip City.
He was a pleasant surprise for the Blazers and finally started to live up to his potential as a true three-and-D wing under Billups. Whether or not he continues to shoot a high percentage from deep will be an under-the-radar storyline to watch in Portland. Was that 22-game stretch an aberration or did Thybulle finally show his ability to shoot after being given the green light to do so?
Regardless, matching the Dallas Mavericks’ offer sheet of 3 years and $33 million seemed like a no-brainer for the Blazers, and Thybulle has a chance to make that contract look silly if he plays as well as he did at the end of last season.
Blazers grade: B+
4. Trading Jrue Holiday
Jrue Holiday needed to be part of the trade that sent Lillard to the Bucks. However, the 33-year-old point guard made no sense on a Blazers roster that already included Henderson, Simons and Shaedon Sharpe. Holiday surely wanted no part of a rebuild either after playing on championship-caliber teams and winning the 2021 NBA Title in Milwaukee.
Only a few days after sending Dame packing, Cronin flipped Holiday to the Boston Celtics for Malcolm Brogdon, Robert Williams III, a 2029 unprotected Boston first-round pick and a 2024 top-four protected Golden State Warriors first-round selection.
Brogdon is staying in Portland for now, but there’s a chance he gets traded at or before this year’s deadline, which would expand the Lillard trade even further, but grabbing additional assets by acquiring Holiday and then sending him to Boston was a shrewd move by Cronin.
When he’s healthy, Williams is an all-defense caliber center. Brogdon is a veteran guard who will be an adult in a young backcourt room as long as he remains with the Blazers. The 2029 unprotected first could end up being valuable given the question marks that could follow the Celtics over the next five seasons.
Holiday will be 38 and likely retired, and will Jayson Tatum and Jaylen Brown still be around?
Blazers grade: A
5. Trading Damian Lillard
Sending away their long-time franchise point guard was a bitter moment for the Blazers – but it ended up becoming bittersweet when the entire return, including the Holiday trade, was announced.
The Phoenix Suns were part of the three-team deal that landed Lillard in Milwaukee. Portland sent Jusuf Nurkic to Phoenix and received Deandre Ayton in return. That’s an immediate upgrade at a position the Blazers have struggled with the past few seasons. Ayton fits into the franchise’s rebuilding timeline at 25 years old.
Portland also grabbed a 2029 unprotected first-round pick from Milwaukee, who will face similar questions as Boston based on the futures of Lillard, Giannis Antetokounmpo, Brook Lopez and Khris Middleton. The Blazers picked up potential pick swaps from the Bucks in 2028 and 2030, as well.
The deal looks even better now than it did when it originally went down as overlooked toss-in Toumani Camara is developing into a legitimate rotation player for Portland.