A roster reshape was expected this summer, but maybe not quite to this extent. The Portland Trail Blazers finally made the Damian Lillard trade, sending their long-time point guard to the Milwaukee Bucks. General manager Joe Cronin then turned around and made another significant deal, this time in the form of a Jrue Holiday trade.
All told, Cronin turned Lillard, Nassir Little, Keon Johnson and Jusuf Nurkic into Deandre Ayton, Robert Williams III, Malcolm Brogdon and Toumani Camara, along with three future first-round picks and a pair of potential first-round pick swaps.
A discussion about the picks is for another day, but Ayton, Williams and Brogdon will be part of a dramatically different rotation for head coach Chauncey Billups.
But just exactly how different will it look?
Portland Trail Blazers starters, rotation after Damian Lillard, Jrue Holiday trades
With a different Blazers roster come different Blazers starters. Billups will have more options at his disposal this season as opposed to last, especially considering Portland’s expectations. Without a mad dash to find the right balance around Lillard and an all-out desperation to make the playoffs, Chauncey will be able to tinker with different lineups throughout the year.

Portland Trail Blazers starters to begin the 2023-24 season
Point guard: Scoot Henderson
Scoot Henderson starting at point guard on opening night against the LA Clippers is as close to a sure thing as you’ll get with the Blazers this year. Henderson is now the face of the franchise. His coaches and teammates had nothing but praise on media day for his leadership and playmaking ability.
Shooting guard: Anfernee Simons
This spot could also go to Brogdon or even Shaedon Sharpe, but Simons has earned the right to continue as a starter and become Portland’s offensive fulcrum. He was the Blazers’ second-leading scorer during a breakout 2022-23 season and was second on the team in usage rate behind Lillard. It’s time for Simons to show how talented of a scorer he is and get the recognition he deserves around the NBA. Don’t be surprised if the 24-year-old makes a push at an all-star berth this year.
Small forward: Matisse Thybulle
Again, another spot that could be handed to Brogdon or Sharpe, but like Simons, Thybulle earned his place in the starting lineup after the way he played following his arrival from the Philadelphia 76ers at last year’s trade deadline. Billups may lean into a more veteran-laden starting five as well, which gives Thybulle the nod over Sharpe. The 26-year-old is one of the league’s best perimeter defenders and shot almost 39 percent from three in Portland after getting the green light to let fly by his head coach.
Power forward: Jerami Grant
There’s a reason the Blazers re-signed Grant to a five-year, $160 million contract this offseason. He proved to be a legitimate third option on offense last year while providing a level of switchable, versatile defense. He could be in for a larger role this year as an experienced vet on a young team.
Center: Deandre Ayton
Billups said on media day (subscription required) that Ayton won’t get Joel Embiid-level touches, but the 25-year-old will be featured offensively as part of Portland’s young core moving forward, and he certainly has the talent for it. The 6-foot-11, 250-pound big man can score on the block, shoot from mid-range and will be an excellent rim-runner and lob-catcher with Henderson, Simons and Brogdon in the pick-and-roll.

The rest of the Portland Trail Blazers rotation
Sixth man: Shaedon Sharpe
If Billups wants an adult in the backcourt, the 30-year-old Brogdon could be the first guy off the bench. This year should be about development, though, and Sharpe should see the court as often as possible. He’s already said he’s willing to start or come off the bench and play the two or the three, which gives Chauncey more ways to get him into the lineup.
Other guards: Brogdon
Portland brought back Skylar Mays, who played well over the final six games last year, on a two-way contract; but Scoot, Simons, Sharpe and Brogdon should soak up all the minutes in the guard rotation. If Malcolm is traded during the season or at the trade deadline, things could change.
Other forwards: Kris Murray, Jabari Walker
Murray was the 23rd pick in June’s draft. He’s considered a plug-and-play, three-and-D wing who can play either forward position. He’s a glue guy willing to do the dirty work – hustle, defend, rebound and spot-up behind the 3-point line. Those skills will get you playing time. Walker could get some run as well.
Backup center: Williams
The man also known as Time Lord could play a number of roles in Billups’ rotation. As long as he’s healthy, he’s as much of a threat as Ayton in the pick-and-roll but is one of the league’s best defensive big men and rim-protectors. He could serve as a direct backup to Ayton, but it’s likely the two spend some time sharing the floor. And as Williams is wildly injury-prone, it’s reasonable to think he comes off the bench and plays fewer minutes than his frontcourt mate.
Henderson (19 years old), Simons (24), Sharpe (20), Ayton (25) and Williams (25) are set up to be the Blazers’ core going forward. Thybulle (26), Grant (29) and Brogdon (30) will play crucial roles this season as long as they’re around. Murray (23) is a rotation lock as well.
The Portland Trail Blazers’ roster is skewed young, but it has a mix of youth and veteran talent, and it’s deeper than it seems on the surface. The Blazers obviously aren’t a contender, but they have the pieces to surprise some teams around the league this season.

