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The Toughest Question Facing the Trail Blazers

Bleacher Report’s Greg Swartz says the big question mark concerns the viability of Portland’s young guard rotation.

2023 NBA Summer League - Portland Trail Blazers v Charlotte Hornets Photo by Ethan Miller/Getty Images

The Portland Trail Blazers are slated to be loaded at the guard position this upcoming season, even if the cosmic, franchise-altering Damian Lillard trade takes place before training camp.

Portland’s best three young players — Scoot Henderson, Anfernee Simons and Shaedon Sharpe — all naturally play either point guard or shooting guard, Sorting out this overlapping backcourt rotation to maximize everybody’s talents and minutes may take some work.

To that conundrum I say, Same as it ever was.

In a recent piece, Bleacher Report’s Greg Swartz called this guard situation the toughest question facing Rip City for the 2023-24 season. “How do the young guards fit together?” Swartz asked to the cosmos.

Imagining a world where Lillard is traded, Swartz sees Henderson as the obvious choice at starting point guard, but wondered exactly how the Blazers will deploy Simons and Sharpe

Simons was a true combo guard last season, spending 42 percent of his court time at point guard and the other 58 percent at shooting guard. The Blazers’ offense was slightly better (117.2 rating compared to 114.5) when Simons was operating as an off-ball guard.

Sharpe actually spent most of his time (44 percent of his minutes) and was his most effective (plus-2.2 net rating) at small forward last season, although he spent time at both guard positions as well. His 6’6” size gives this lineup some added versatility.

This young crop of guards is the most exciting part of Portland’s inevitable rebuild. Seeing how they mesh will determine the team’s success in 2023-24 and beyond.

Playing undersized small forwards has become somewhat of the norm in Portland recently. Last season the Blazers slotted 6-foot-4 Josh Hart at the three-spot, when he was probably better suited as a shooting guard. Before that it was 6-foot-4 Norman Powell. While Sharpe is the tallest of the bunch, giving more conventionality to a three-guard lineup featuring him at small forward, it again may be forcing a square peg in a round hole. That might not be best for his development, but maybe he can show he’s more than capable of sticking with NBA forwards.

For Simons, he seemed to struggle at times last season as a natural, ball-dominant scorer being pushed to an off-ball position in the starting lineup. He looked much more comfortable during his breakout 2021-22 season, consistently operating the pick-and-roll with Jusuf Nurkic and easing into step-back triples off the dribble.

The new variable, of course, is Henderson, the shiny new No. 3 overall pick. Henderson’s hyper-athletic point guard game seems to be more geared toward distributing than his Hall-of-Fame predecessor, one of the deadliest scorers on earth with a basketball. Maybe he can be the straw that stirs this guard situation into a palatable cocktail? Or maybe Head Coach Chauncey Billups will have to get creative with rotations and staggering to ensure he’s putting Henderson, Simons, and Sharpe in the best positions to succeed.

As Swartz points out, how this guard rotation plays together and develops individually this upcoming season will be the biggest indicator of where this new iteration of the Blazers is heading.