There are seven players that Chauncey Billups could start for the Portland Trail Blazers this season. Two have to be the odd ones out, and it very well could be Portland's rising stars, Scoot Henderson and Shaedon Sharpe.
To be clear, nothing is set in stone, and plenty can change between now and the Blazers' first regular-season game on October 22. But Billups has a tendency to lean on his veterans, and we expect him to do the same this time around.
Blazers' pressure to win now could force Henderson and Sharpe to the bench
The three players that should be considered near-locks in Portland's starting five are frontcourt pieces Deni Avdija, Toumani Camara, and Donovan Clingan. They have emerged as the true building blocks for the Blazers, and having two versatile wings alongside a 7-foot-2 rim protector goes a long way in establishing their defensive identity.
Another player who will significantly help in that department is newly acquired Jrue Holiday, giving Portland an elite perimeter defender to add to the mix. The trade for Holiday was puzzling in itself, but it would even be more confusing if Portland invested north of $100 million into a 35-year-old guard to bring him off the bench. The Blazers believe it's winning time in Portland, which is a primary reason why they went out and got the overpaid guard in the first place. At this point, it would be foolish not to start him as Holiday gives them the best shot at winning and has a strong case to make as Portland's best player despite his declining play.
That leaves Billups with one spot remaining between Henderson, Sharpe, and the polarizing veteran, Jerami Grant. This isn't what we would necessarily do. If this were NBA2K and it were up to us, Holiday wouldn't be on the team, and Henderson and Sharpe would be starting in Portland's backcourt while they endure another season of developmental growing pains and potentially land a valuable top ten pick to add to their young core. But given their current situation, it wouldn't be surprising at all if Billups elects to start Grant.
With Tom Dundon set to take over as the Blazers' new owner in 2026, Billups and general manager Joe Cronin likely feel more pressure to win sooner rather than later. Say what you will about Grant's contract, but he still gives them the best shot to keep their jobs. Grant is due for positive regression after a down season in which he averaged 14.4 points while shooting just 37.3% from the field. And at 6-foot-7, he is a much better fit defensively for what Portland is trying to accomplish as a switchable team that gets stops that lead to transition opportunities.
It's an unnecessarily complex situation that the Blazers have gotten themselves into. They are a rebuilding team that not only held onto their veterans for far too long but also went out of their way to add more to their roster. Now, the timelines are even messier, and it could result in their two high-upside guards coming off the bench for yet another season.