Prediction: Who will be the Trail Blazers’ best player in 5 years?

The Portland Trail Blazers are expected to lose one of the best players in franchise history in Damian Lillard, whether it’s sometime this summer or during the 2023-24 season. That begs the question: Once Dame is gone, who will take over as Rip City’s main attraction?

This article identifies three standout contenders to be the Blazers’ best player five years from now. Then, it provides a prediction after analyzing various factors, including each candidate’s skill set, strengths, weaknesses and developmental trajectory.

There are legitimate cases to be made for each player, which is an excellent sign that the Blazers are on track to have a promising future in the post-Lillard era as they begin to retool around these players.

Candidate No. 1: Scoot Henderson

Scoot Henderson was the No. 3 overall pick in the 2023 NBA Draft out of the G League Ignite. Last season with the Ignite, Henderson averaged 16.5 points, 6.5 assists, 5.4 rebounds, 1.1 steals and 3.5 turnovers on 43/28/76 shooting splits in 30.7 minutes per game.

The case for Henderson

Henderson is still only 19 years old and has plenty of time to maximize his untapped potential and reach his ceiling. By most NBA players’ career standards, he will still not have entered his prime five years from now. However, athletic guards tend to enter their peak a bit earlier.

For example, Derrick Rose won his MVP at age 22. Henderson, a 6-foot-2, 195-pound guard, has a highly similar play style to Rose, utilizing his explosiveness to complement his downhill attacking style. Henderson frequently gets by the first level of defense due to his ballhandling and athleticism.

As a result, he also gets teammates involved when necessary, as off-ball defenders are forced to help on his drives.

While Rose was an MVP outlier as the youngest player to win the award, it shows that athletic guards entering the league can succeed early. As a result of these players’ similarities, Henderson could enter his prime a bit earlier than typical NBA players.

Additionally, five years will be plenty of time for Henderson to improve his current weaknesses, primarily his shooting. If he can become a reliable 3-point shooter in the next half-decade, Henderson has a legitimate case to become an all-star. He’ll have every opportunity to develop in Portland as the organization looks to retool around its youth.

The case against Henderson

There is no concrete history of how Henderson will fare in the NBA. Henderson’s G League experience will benefit his NBA readiness compared to other rookies, giving him a solid case to be considered one of the favorites for Rookie of the Year. Still, Henderson will have a steeper learning curve to acclimate to the NBA style of play than the other Blazers players who have been around longer.

Additionally, Henderson needs to become a more well-rounded and versatile player. The primary aspects he needs to improve are his shooting, decision-making and defensive impact.

If Henderson can’t develop his weaknesses in the next half-decade, he could become closer in talent to someone like Collin Sexton rather than Derrick Rose or Russell Westbrook. He’s already a starting-level player on day one entering the league, but he won’t be the best Blazers player in five years unless he can unlock more aspects of his game.

Candidate No. 2: Shaedon Sharpe

Now entering his second season, Shaedon Sharpe is a 6-foot-6, 200-pound guard out of the University of Kentucky, which he attended but didn’t play.

He was the No. 1 overall recruit in the 2022 class, reclassified to attend Kentucky, yet only practiced with the team. As a result, Sharpe was a coveted NBA draft prospect, yet a relatively unknown player compared to other lottery selections.

The Blazers took a flyer on Sharpe’s potential and athleticism, selecting him with pick No. 7 in the 2022 NBA Draft. So far, the risk has certainly paid off.

The case for Sharpe

He had a productive rookie season in Portland, averaging 9.9 points, 3.0 rebounds, and 1.2 assists on 47/36/71 shooting splits in 22.2 minutes per game.

One of the most promising stretches of the season for Sharpe was toward the end when the Blazers decided to shut Lillard down. As a result, Sharpe received an increase in playing time and capitalized on it. Sharpe recorded 15 games as a starter last season, and during that time, he averaged 18.5 points, 4.9 rebounds and 3.1 assists with similar efficiency.

Because Sharpe reclassified, he’s still only 20 years old and will be on the cusp of entering his prime five years from now. However, the tantalizing talent, athleticism and potential he displayed toward the end of last season make a great case for him to be the Blazers’ best player.

The case against Sharpe

Similar to Henderson, Sharpe must improve his shooting, playmaking and defense. Both are incredibly athletic guards (arguably the most explosive in the league) with enough talent to give them all-star-level potential.

Offensively, Sharpe is a good but not elite 3-point shooter at this point in his career. He isn’t a playmaker and doesn’t get teammates involved very often, as evidenced by his 1.2 assists per game last season.

He’ll need to improve his 3-point shooting in order to become a three-level scoring threat. If he isn’t going to be a great playmaker, then Sharpe will have to find ways to continue to improve what he is best at, which is being a crafty, slashing scorer.

Defensively, Sharpe was a negative. He had a defensive RAPTOR rating of -2.7 last season. The good news is that he has the physical tools to be a solid wing defender at 6-6 with his quickness. Now it’s just a matter of gradually improving through experience.

The case of Henderson versus Sharpe may boil down to who can improve their weaknesses the most. We already know they will be solid, if not elite, scorers in the league. But who can truly impact winning outside of scoring through their decision-making and defense?

Candidate No. 3: Anfernee Simons

The 24th overall pick in the 2018 NBA Draft, Anfernee Simons has proven to be a steal for the Blazers. Simons had a quietly productive season last year, averaging 21.1 points, 4.1 assists and 2.6 rebounds on 45/38/89 shooting splits.

The case for Simons

Simons has become an under-the-radar player who should only continue to improve next season. He’s still only 24 and will be given plenty of opportunity to become a focal point of the franchise, especially with the seemingly inevitable Lillard trade.

While the Blazers are crowded at the guard position with Henderson, Sharpe and Simons, the one most capable of playing both roles as a combo guard is Simons. He possesses the best combination of shooting and playmaking out of the three.

The main advantage Simons will have over the other two players will be his elite shot-making ability. With Henderson and Sharpe’s ability to drive and cause the defense to collapse, Simons could be the primary beneficiary of many open looks. There’s a reasonable path to Simons averaging more than 25 points a game in the coming seasons.

Don’t count out Simons as the Blazers best player. In the next five years, he’ll be in the midst of his prime. He’s talented enough to become an All-Star in the coming seasons with increased opportunity.

The case against Simons

The case against Simons is his lack of potential as a two-way player due to his frame. The pairing of Lillard and Simons was never ideal because they both are undersized and somewhat negative defenders. Because of his overlapping skillset with Lillard and his below-average defense, Simons can frequently get overlooked.

He’ll have his chance to get more recognition this season but must improve on the defensive end. Last season, Simons had a negative defensive RAPTOR rating of -0.7.

Additionally, Simons needs to take that next step on offense and become a true playmaker and get others involved more. He can only be so impactful as a scorer and efficient shooter beyond the arc. He will likely never be a great defender, so he must contribute in multiple aspects on the offensive end to truly impact winning at a high level.

Compared to Henderson and Sharpe, Simons has already tapped into most of his potential. While Simons’ numbers should improve again this season due to his increased opportunity, he is more of a finished product than the others. Five years from now, he could be a similar player to what he currently is.

Prediction: Shaedon Sharpe

Sharpe took the league by storm following the All-Star break and should continue to build on his stellar play going into next season with an increased role. After all, there’s a reason Sharpe was the No. 1 overall recruit in the class of 2022 before he decided to reclassify.

Of the three players, Sharpe is the one who has the ideal combination of shooting, size and athleticism. Henderson can get to the rim at will, yet he has some questions surrounding his shooting. Simons is an excellent shooter, yet is capped athletically in terms of his frame.

Meanwhile, Sharpe possesses all the necessary tools to become a star in the league. He has extremely high potential as a multi-level scorer, which could make him an all-star sooner rather than later.

The talent, athleticism and work ethic are all there. Sharpe had a much better season than his 9.9 points per game suggests.

However, aspects of Sharpe’s game still need improving as he enters his second year. As previously mentioned, he was negative defensively and seemed out of place at times. Sharpe also needs to improve as a playmaker, as he averaged nearly a 1:1 assist-to-turnover ratio last season.

Sharpe has all the traits to become an elite scorer in the league. If he can hone his playmaking and utilize his athleticism to improve defensively, there’s undoubtedly a pathway for Sharpe to become the Trail Blazers’ next best player.

Five years from now, he will be on the cusp of entering his prime at age 25. It will be a pleasure to watch Sharpe’s development between now and then as the Blazers begin to embrace this team’s new era.