The Portland Trail Blazers surprisingly traded for 35-year-old guard Jrue Holiday (again) this summer. Portland is bringing in the two-time NBA champion to help make a play-in push in the Western Conference and provide valuable mentorship, particularly for Scoot Henderson.
However, this trade now gives Chauncey Billups a rotation dilemma. Does he prioritize winning or development?
Jrue Holiday has the Blazers rethinking their rotation
Despite his declining play, starting Holiday still gives Portland its best chance at winning. It also wouldn't make sense to take on his massive contract just to bring him off the bench.
But at the same time, the Blazers already have three core frontcourt pieces seemingly locked into their starting lineup between Deni Avdija, Toumani Camara, and Donovan Clingan. To start Holiday would mean bringing at least one of Henderson or Shaedon Sharpe off the bench, defeating the purpose of bringing him in to aid their young core's development.
The silver lining is that Holiday is one of the most versatile guards in the association and can effectively play positions one through three, giving Billups much more flexibility when constructing his rotations.
"I think I play every position," Holiday said. "I've proven that and shown that throughout my career. I'm a complete basketball player. You can't put one position on someone, the way the game is changing now. Guys who have never played point guard are coming into the league and playing point guard. I'm a good fit with anyone."
Holiday had just a 15.9 usage rate last season with the Boston Celtics, the lowest of his career. At this stage, he isn't a primary playmaker, but can still impact winning without requiring the ball. That's a perfect fit for Portland's backcourt as it still allows for increased opportunities for Henderson and Sharpe, regardless of which direction Billups decides to take his starting lineup.
A unit consisting of Henderson, Camara, Avdija, and Clingan had a minus-6.2 net rating last season, which Billups must also factor in. Does Holiday's veteran and two-way presence improve that unit enough? That's an elite defensive group and could result in a top ten-ranked defense for Portland in 2025-26. However, it's also not well-balanced, as scoring and playmaking will be challenging to come by.
The Blazers are entering a pivotal phase in their rebuild as they look to end a four-year playoff drought. Holiday certainly helps them achieve that goal, but Billups can't lose sight of the big picture. Portland's ceiling will be determined by how much its young core continues to develop, and Holiday must be utilized as someone who aids that development rather than a focal point of the roster. It's on Billups to find the right balance between youth and veterans, which is a difficult but essential task this season.