Obvious conundrum makes the Trail Blazers' next smart move crystal clear

Portland Trail Blazers have no desire to win a significant number of games next season. Although Shaedon Sharpe and Scoot Henderson are considered foundational pieces in their rebuild, one of these players will likely have to come off the bench, which seems counterproductive for a team trying to position itself for a top draft pick next summer. This situation forces head coach Chauncey Billups to decide which player should take on that role, but it's a choice that shouldn't even have to be made in the first place.

Meanwhile, GM Joe Cronin must answer a bigger-picture question about their backcourt conundrum. Specifically, what to do with Simons and determine whether or not all three of them can stick around long-term without hindering each other's productivity and development. The three of them shouldn't all start together as it would be too big of a defensive liability due to their lack of size and defensive awareness at this stage of their careers.

Blazers must trade Anfernee Simons soon

Sharpe is set for a significant third-year jump, and if there's one player that Portland had to pick to build around and bet on long-term, it should be him. But that leaves Henderson as the odd man out. That is, barring a Simons trade, which is the next move that Portland must make.

Simons is just now entering his prime at 25 years old and coming off a career-best season on a per-game basis, in which he averaged 22.6 points, 5.5 assists, and 3.6 rebounds on 43/39/92 shooting splits. He's also on the books for $25.9 million this upcoming season and $27.7 million in 2025-26; that is a very reasonable, if not undervalued, contract for Simons.

These factors suggest it would be easy for the Blazers to find trade partners and get significant assets in return that would help them balance out their roster better, whether that's a young wing, draft capital, or a combination of the two, which Cronin has leaned towards in his past deals.

Waiting too long to move Simons could hinder the Blazers' future backcourt development. It also runs the risk of a few things that could potentially impede his trade value. If they don't decide to trade him until next season, and Simons demands closer to a max contract in his next deal, teams could be more hesitant to give up a lot of assets. Not to mention the possibility of him leaving in free agency.

Additionally, Simons has made it clear that he wants to have the chance to win, which the Blazers have no intention of doing anytime soon. If Simons eventually requests a trade out of Portland (which seems possible, especially since he may not feel they value him as much if they are focused on building around Henderson and Sharpe), then the Blazers would also lose leverage in trade negotiations.

The Blazers must move Simons soon to improve their chances of landing a top pick in the 2025 NBA Draft, maximize their return in any potential deal, and, most importantly, give Scoot and Sharpe the keys to the backcourt.