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Rupert appeared in 39 games, including 12 starts, for a Blazers team that dealt with a plethora of injuries during the 2023-24 season. However, Portland expects to be healthier in 2024-25, and if that's the case, the franchise would prefer to oversee Rupert's development in the G League, where he'd be able to play more minutes on a regular basis, rather than in the NBA where he'd be limited to a minor role off the bench. Rupert averaged 4.0 points, 2.4 rebounds and 1.6 assists per game in his 39 NBA appearances in 2023-24.