3 Pressing questions Blazers need to answer down the stretch of the regular season

What does Portland still need to learn about certain players and coaches?

Deandre Ayton (left), Chauncey Billups; Portland Trail Blazers
Deandre Ayton (left), Chauncey Billups; Portland Trail Blazers / Chris Coduto/GettyImages
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The 2023-24 season was never going to be about wins and losses for the Portland Trail Blazers. It was always going to be about player development and the future of the franchise. Long-term questions needed answers.

How good would/could Scoot Henderson be after the organization made him the No. 3 pick in the 2023 draft? Could Anfernee Simons make the jump from secondary scorer to primary offensive option? How much better would Shaedon Sharpe be in his second NBA campaign? It's fair to say those questions still don't have concrete answers.

But the Blazers needed to address other issues, too, and the jury is still out on those as well. Here are three that need to be solved down the stretch of the regular season.

Is Chauncey Billups the right coach to develop Portland's young players?

Has there been improvement across the Blazers roster this season? Certainly. Is it enough to convince general manager Joe Cronin and the front office that Chauncey Billups is the right person to continue that advancement?

Henderson stood to benefit the most from Billups' coaching. The latter was an NBA-champion point guard himself, and when Scoot struggled to start the season, Billups' playing days helped him relate to the 20-year-old. Chauncey was traded midway through his rookie season and played for four franchises before settling in as the leader of the Detroit Pistons.

Scoot has shown improvement during an up-and-down campaign, but he hasn't been the player Portland hoped - at least not yet.

Save for injuries, Simons has improved across the board. He's averaging career highs in points, assists, rebounds, field-goal attempts and free-throw attempts. He hasn't had the major breakout season some people expected, but he's proving he can be a key piece on a contending team.

Sharpe was having that breakout season. In 25 starts from October to mid-December, the 20-year-old was averaging 16.9 points, 5.3 rebounds, 3.3 assists and nearly 1 steal while hitting 37 percent from three and getting to the foul line with increased frequency. Then he suffered an adductor injury and only played six more games before he was forced to have surgery and potentially miss the rest of the season.

Other young players like Jabari Walker and Toumani Camara took steps forward under Billups, too. But the question remains: Was the player development this season enough to convince the Trail Blazers that the 47-year-old is the right coach to morph this young core into a contending team?