The Portland Trail Blazers will gather for training camp in about a month. Whether Damian Lillard is still on the roster at that point or not, the 2023-24 season should look drastically different than the past few years.
With Lillard at the helm, the goal was at least a playoff berth, if not a real postseason run. It’s arguable if that goal was realistic, but it was the plan nonetheless.
But with rookie point guard Scoot Henderson taking over, second-year guard Shaedon Sharpe ready for more minutes and the primary scorer role being handed to Anfernee Simons, it’s fair to expect a youth movement with some growing pains this year.
And with the change in approach from championship idealism to developmental patience, a few members of Portland’s organization should be heading toward camp this fall with added motivation.
Trail Blazers with something to prove during 2023 training camp
Player No. 1: Nassir Little
This may be a make-or-break season for Little. The 25th overall pick in the 2019 draft has shown glimpses of what he can be – an athletic three-and-D wing capable of developing into an NBA-level starter. So far, though, those glimpses are all he’s shown.
Nas has played more than 48 games in a season just once in his four years in the league. That was last year, when he played in 54 contests before being shut down with a core injury in April, but his role had diminished even before that. After starting 23 games and averaging nearly 26 minutes in 2021-22, Little started just four times last year and played 18 minutes a night.
His production dipped across the board. He averaged just 6.6 points and 2.6 rebounds on 44.2 percent shooting, although his 3-point percentage did rise from 33.1 percent to 36.7 percent, albeit on fewer attempts (2.9 per game).
But with Sharpe likely soaking up more minutes on the wing so head coach Chauncey Billups can get him on the floor with Scoot and Simons, rookie Kris Murray getting at least developmental minutes if not more, Jerami Grant back as the starter at the four and Matisse Thybulle likely starting at the three, Little will need to stay healthy and play well to prove he belongs in Portland’s rotation.+

Player No. 2: Anfernee Simons
Simons had his breakout season in 2022-23, even if it went largely unnoticed on a national level. He proved himself as a legitimate NBA scorer, averaging more than 20 points for the first time in his career on 45/38/89 shooting splits.
That 3-point percentage is even more impressive considering it came on 9.1 attempts per night.
There would be nights when Grant was feeling it and would play second fiddle to Dame, but for the majority of the season it was Simons who led the offense when Lillard either sat or missed time.
Scoot may be the new guy on the block and Sharpe may be getting most of the offseason hype, but it’s Ant who should be ready to prove himself as Portland’s go-to scorer whenever Lillard exits.
With a higher usage rate and shot volume Simons’ shooting percentages may take a bit of a drop, but his counting stats should take a leap, as should his standing in the league.
It’s time for the 24-year-old to push for an all-star berth and show he’s one of the better scorers in the NBA.

Player No. 3: Shaedon Sharpe
While Little needs to prove himself this year and Simons is poised to, it feels like Sharpe is under the most pressure to show a real level of improvement.
The 20-year-old showed at the end of last season he can carry an offense – even one on a losing team at the height of tanking season.
It’s been thrown around a lot this summer, but it bears mentioning again: In the final 10 games of 2022-23, the rookie played more than 35 minutes a night and averaged 23.7 points, 5.8 rebounds, and 4.2 assists on 46/36/78 shooting splits. He had games of 24, 29, 30, 27, 27 and 26 points.
Although that stretch showed Sharpe’s ability to score in bunches, it also set the bar extremely high for a player who remains raw entering his second professional season. (He had 3 turnovers on five different occasions and at least 5 in three others during that 10-game span.)
Billups had a hard time trusting the then-rookie with real minutes in important stretches because of his lack of knowledge and grasp of the NBA game. Shaedon’s defensive rating of 118.4 was worst on the team for any player who played more than 40 games and averaged at least 20 minutes.
That number is worse than both Lillard and Simons, two small guards dramatically limited on that end of the floor. Sharpe’s size, length and athleticism should make him an above-average defender, which he’s far from being at the moment.
The raw, physical skills are clearly there, but it’s the development in the other parts of his game – defense, rebounding, playmaking, efficiency – that he needs to show in order to prove himself as a future star in the league.

Trail Blazers General Manager Joe Cronin
In December, it will be two calendar years that Portland has been under the watch of Cronin. He’s had two nearly full offseasons and one trade deadline to put his stamp on the Blazers’ roster. So far, his tenure has not been popular among Rip City fans.
Cronin repeatedly preached patience when it came to building a team that could help Lillard compete for a title. Some of his moves have panned out – drafting Sharpe, trading for Grant and getting a first-round pick that became Murray in exchange for Josh Hart, who was likely leaving after the season anyway.
Others – the Gary Payton II debacle – haven’t gone as planned.
What’s worse, the optics of failing to fulfill that promise to build a contender around Lillard – whether fact or not – that culminated in drafting his potential successor in Henderson and Dame finally asking to leave Portland have earned him no favors among the fan base.
Whatever Cronin decides to do when it comes to the inevitable Lillard trade, whether that’s tomorrow, before training camp, at the trade deadline or at any other point – will define his career as an NBA GM.
If he hits a home run and the Blazers kick off a full rebuild with Henderson, Sharpe, Simons and a haul of assets from a Lillard trade, things will be rosy, or at least as rosy as possible. If whatever return he gets is underwhelming, though, and he misplays his hand, Cronin will have a serious amount of work to do – in Portland’s front office and in the court of public opinion.

