The Portland Trail Blazers have finally done it. After months of rumors and speculation and smokescreens and opinions, starting well before Damian Lillard’s trade request and continuing daily until now, the Trail Blazers have executed a trade. Damian Lillard, future Hall of Famer and a strong candidate for the greatest Blazer of all time, will now officially play for another team.
That team is, shockingly, the Milwaukee Bucks (Woj first on the trade). The Eastern Conference contender, perhaps motivated by Giannis Antetokounmpo’s wandering eye, threw its hat into the ring and came away with an all-NBA point guard. The offensive fit between Giannis and Dame is positively divine.
The return for the Blazers is certainly not what many expected; it’s not a gift basket of draft picks and draft prospects. Instead, Portland now has two max players to fit onto the team, at least for as long as they are on the roster. Here are the full details of the trade:
Full trade, per sources:
— Shams Charania (@ShamsCharania) September 27, 2023
- Bucks: Damian Lillard
- Blazers: Jrue Holiday, Deandre Ayton, Toumani Camara, 2029 first-round Bucks pick and Bucks pick swap
- Suns: Jusuf Nurkic, Nassir Little, Keon Johnson, Grayson Allen https://t.co/56I888abMs
Jrue Holiday is a multi-time All-Star and was the second-best player on a title team just over two years ago. Deandre Ayton is a walking double-double and former No. 1 overall pick. Even as Portland engages other teams on a possible trade for Holiday and other veterans, they head into training camp next week with an intriguing mix of vets and youngsters.
Who’s in the Portland Trail Blazers rotation now?
How will things shake out for the starting lineup? Who fills out the rotation? And if you leave head coach Chauncey Billups with all of his clubs in his bag, will he choose to prioritize development or winning?
Let’s take a crack at building out a starting lineup and rotation after the Damian Lillard trade.

Trail Blazers: Starting lineup after Damian Lillard trade
Portland moved one starter and added two players who haven’t come off the bench for hundreds of games. How do they fit into the youth movement?
Point Guard: Scoot Henderson
It’s not a lock that Scoot Henderson will start if Jrue Holiday is on the roster in a month when the season begins, but top-3 picks tend to find their way to the starting lineup, especially if they are as polished as Henderson.
Shooting Guard: Shaedon Sharpe
The No. 7 pick in the 2022 NBA Draft has done nothing but show flashes of immense potential, and the expectation is that once he forced his way into the starting lineup down the stretch for Portland last season, he was never going to relinquish the spot.
Small Forward: Jrue Holiday
This is the big question mark for the Portland Trail Blazers: who will start at the 3? One option is to start Anfernee Simons at shooting guard and slide the 6-foot-5 inch Sharpe over to the 3, but he isn’t built out enough to do anything but wave to opposing small forwards as they go by.
Holiday is a veteran who deserves to start, and his defensive ability on the wing should place him there. Matisse Thybulle is a strong candidate to start as well given his defensive ability,
Power Forward: Jerami Grant
The Trail Blazers will trade Jrue Holiday, probably before the season begins. They will almost certainly trade Jerami Grant by the time the trade deadline rolls around, as the highly-paid veteran forward is much more valuable to a contender than to the retooling Trail Blazers.
Center: Deandre Ayton
The Trail Blazers finally have their center after taking part in trade rumors for nearly every other pivot in the league. Jusuf Nurkic is replaced by Ayton, who is a physical marvel and has a high floor on both offense and defense. Will he take a step forward to become excellent on either end? That remains to be seen.

The rest of the Blazers’ rotation after Lillard trade
The idea that Anfernee Simons wouldn’t start for Portland seems crazy, and it may end up that his seniority wins out. Yet for as good of a scoring threat as Simons is, he doesn’t have the on-ball creation to be a full-time point guard and he is generously listed at 6-foot-3. He looks like a long-term sixth man.
Thybulle is also a lock to be in the rotation; Billups and the front office both seem to really like him, and he is a defensive playmaker who can sow lineups together on that end. The Blazers seem like a lock to sign a center such as Bismack Biyombo, but for now, Moses Brown will get a few minutes as Ayton’s backup.
From there, things get more interesting. There aren’t a lot of veterans left, which means it’s a youth movement to fill out the rotation. Does Billups lean toward Jabari Walker or Kris Murray to play backup forward minutes? Walker was a surprise as a rookie but Murray has greater offensive upside.
The rest is a grab bag of raw prospects that Billups is unlikely to insert into the rotation unless he is forced to. That includes Toumani Camara, who came over in the Lillard trade, and rookie Rayan Rupert, on the wing. Their minutes likely increase as the season goes on.
Things will continue to change as Holiday and Grant are eventually traded, but for now, this is the roster and how the starting lineup and rotation might shake out.

