Trail Blazers Position Preview: Shooting Guard

The 2024-25 Portland Trail Blazers have a variety of shooting guard options entering this season, although each is still fairly inexperienced and developing.

Let's analyze what the likely depth of their position looks like in a season that seems to be all about development again.

Read more: Trail Blazers 2024 Position Preview: Point Guard

Sharpe is expected to assume the role of starting two guard, while former starting shooting guard Anfernee Simons is slated to become the club's starting point guard. The 6'6″ Kentucky product saw a massive uptick in performance during the 2023-24 season, averaging an encouraging 15.9 points on a .406/.333/.824 shooting average, 5.0 rebounds, 2.9 assists and 0.9 steals per night.

A two-time All-Defensive Team selection with the Philadelphia 76ers, Thybulle has had a rough patch since arriving in Portland midway through the 2022-23 season. After starting all 22 games in his first season, he was benched in 2023-24. In 65 healthy games last year, he averaged just 5.4 points on a rough .397/.346/.759 shooting line, 2.1 rebounds, 1.7 steals, 1.4 assists and 0.8 blocks per night. Thybulle's jump shot is such a problem — and head coach Chauncey Billups clearly didn't value his contributions on defense enough — that the team opted not to use him as a starter.

Still, Thybulle – who can play both shooting guard and small forward – is one of the team's few good wing defenders, along with power forward Jerami Grant. Like Grant, Thybulle is a potentially overpaid veteran who could be used as a trade at some point.

Rupert was drafted No. 43 in 2023 and could get more playing time. In 39 games with Portland last year (12 starts), he averaged 4.0 points on a .335/.359/.760 slash line, 2.4 rebounds and 1.6 assists per game. In six regular season games for the Trail Blazers' NBAGL affiliate, the Rip City Remix, he averaged 12.7 points, 6.0 rebounds, 1.7 assists and 0.8 steals per night.

There is a possibility that Anfernee Simons, who is now set to be demoted to the team's starting point guard position again, could play some minutes at the number two position alongside his own backup point guard Scoot Henderson.

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