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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?
Andrew Hanlon
Andrew Hanlon

Rip City Project

Deandre Ayton (left), Chauncey Billups; Portland Trail Blazers / Chris Coduto/GettyImages

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?

Is Deandre Ayton the Blazers' center of the future?

It's been a tale of two seasons for Portland's new big man. Or perhaps, more accurately, a tale of most of the season and the last month. He's been in and out of the lineup with nagging injuries and when he has played, he's putting up some of the worst numbers of his NBA career.

In the eight games he's appeared in since Feb. 10, though, he's been a completely different player. In fact, he may be Portland's best player at the moment.

During that span (he still missed six more games), Ayton is averaging 19.3 points, 13.8 rebounds and 2.2 stocks (steals plus blocks). Across a full season, those would all be career highs for the 25-year-old.

Billups called Ayton a top-five center before the season. He's paid like one, but he's never lived up to the immense talent that made him the No. 1 pick in 2018. The 7-footer has size, athleticism, agility, speed and an offensive tool kit that most players his size don't. To this point in his career, though, he's never become the dominant big man he is on paper.

Will the Blazers get this current version of Ayton or the one who has struggled for most of the season? What he does over the final month will go a long way in helping the front office decide if the center position is still a need or if it belongs to Ayton moving forward.

What should the Trail Blazers target in the draft?

The most obvious hole on Portland's roster right now is a big wing that can defend. Scoot and Simons are 6-foot-2 and 6-foot-3, respectively. Sharpe could be that guy, but he's 6-foot-5 and isn't a great defender yet.

A 6-7, 6-8, long athletic player who fits the three-and-D mold seems like the ideal player to add to the Blazers' roster. Jerami Grant is a combo forward, but he's an above-average defender at best, has more of a scorer's mentality and is 29 years old. A young player who's more defensive-minded and can space the floor but is willing to settle into a role and grow with a pair of would slide nicely onto Portland's roster.

Zaccharie Risacher, Cody Williams, Stephon Castle, Tidjane Salaun and Ron Holland are potential lottery picks in the 2024 NBA Draft who have skill sets that check some of those boxes.

A guard to take over Malcolm Brogdon's role off the bench could be another option, but at this point in the team's rebuild, taking a best-player-available approach to the draft is the right idea.

Andrew Hanlon

Andrew Hanlon

Andrew is a Site Co-Expert for Pippen Ain't Easy. He earned a degree in Journalism from the University of Wisconsin-Oshkosh and began covering high school sports in 2014. He's covered the NBA since 2021, and his work has been featured on FanSided, SB Nation, Yahoo! Sports, Sportscasting, and GiveMeSport. He’s been in his PAE role since 2024 and previously held the Site Expert position for Rip City Project (Portland Trail Blazers). When he's not writing about, talking about, or watching sports, he can be found playing and coaching them with his five kids.