Kris Murray, Toumani Camara, Jerami Grant and the Blazers' wings
Jerami Grant
Grant doesn't have much to prove at this point in his career. He's established himself as one of Portland's best players, and before this hamstring injury (which could be a way of keeping him on the bench and letting the young guys get more minutes) he showed his durability and consistency.
The biggest question facing Grant is whether he can prove he's worth the five-year, $160 million contract the Trail Blazers gave him before the start of this season.
Matisse Thybulle
Like Brogdon and Grant, Thybulle is who he is - an excellent perimeter defender who can knock down some open threes.
There really isn't a critical question facing the 27-year-old who's already locked down a role as a versatile three-and-D guard/wing, but it would make Portland a little more comfortable if he can add something to his game to justify the potentially $22 million he's owed the next two seasons.
The Blazers are up against the luxury tax, which isn't an enviable position to be in for a franchise in their position. The most highly-paid, veteran players like Thybulle need to prove they're worth the money.
Kris Murray
Murray has steadily improved after landing a starting spot and consistent minutes since Feb. 23. He's averaging 8.9 points, 5.4 rebounds and 1.1 steals in more than 30 minutes a night in those 16 games.
His shooting percentages still leave a lot to be desired, though. He has splits of 43/25/64 in that stretch. But he's scored in double digits in nine of those 16 games, including a career-high 21 against the Clippers when he shot 3-of-6 from three and added 7 rebounds and 3 steals.
The question: Can Murray keep getting better and earn a role on a healthy Portland team?
Rayan Rupert
Rupert was an unexpected marksman from deep during his time in the G League this season. He's still only 19 and entered the draft as a potential lockdown wing defender with his length and athleticism, and that potential is still there. He just needs to get stronger and gain more experience.
His 3-point percentage has translated to the NBA level, though, which is incredibly promising. He's shooting 37.5 percent from deep with the Blazers.
The question: Can Rupert continue to improve and eventually become a starting-caliber three-and-D wing for the Blazers? (Bonus question: How high is his ceiling?)
Toumani Camara
Camara's question and his goal for the offseason is an easy one. Can he develop a consistent 3-point shot? He's already an established defender but he's only shooting 32.3 percent from deep. Bumping that up to 38-ish could make him a completely different player.
Justin Minaya
Copy-paste the same question Hagans is facing: Can he have a good enough offseason to show the front office he deserves a roster spot next year?