The Portland Trail Blazers backcourt will play a big role in the franchise’s next rise up the standings. Chock full of talent, the current incarnation currently lays claim to Anfernee Simons, Scoot Henderson, and Shaedon Sharpe — three young prospects with a tantalizing range of specialties and skill sets.
All three have started for the Blazers at various stages this season with varying levels of success. Sharpe’s size and length make him more of a wing with his ability to operate off the ball. Unless something dramatic happens, the sophomore athlete will grow into the starting shooting guard spot full time.
As for Henderson, the arrival of the 19-year-old at the 2023 NBA Draft prompted Damian Lillard to ask out, given the G-Leaguer’s age and the fact that the two play the same position.
Simons is still only 24, serving as the Blazers’ offensive leader in his sixth NBA season. He too is optimized at point guard. Simons’ presence would have also exacerbated the positional logjam if Lillard had stayed.
Having said that, Simons and Henderson probably can’t spend their entire careers as teammates. Neither is likely coming off the bench long-term given Simons’ ability and Henderson’s potential. Their lack of size also makes a Simons-Henderson backcourt flawed defensively, not to mention the fact that each is more effective when they’ve got the ball in their hands.
For those suggesting playing Sharpe at the three, I just can’t see it. It’s unfair on the young Canadian's development, competing with opponents at the bigger wing position.
We should also mention Malcolm Brogdon. The veteran point guard was an asset earned as part of the Lillard deal but all signs suggest the reigning Sixth Man of the Year will be playing elsewhere come February 8.
2023-24 Stats: 33.0 mins, 22.9 points, 38.3% 3pt on 8.5 attempts, 3.5 boards, 4.9 assists, 0.5 steals
While he’s not a finished product, Simons already has an impressive body of work behind him. But the former Slam Dunk Contest champion has only just started scratching the surface of his ability, following the departure of Lillard in the offseason.
In November, I suggested Simons would be moved by the Blazers before Jerami Grant. I was wrong but to be fair, Simons, despite injury and illness, has been able to improve his game this season, including increasing his free throw attempts from 2.9 to 4.7 a game.
He’s also had his share of off nights. But much of his struggles can be put down to the fact that opposing defenses aren’t really concerned with any Blazers not named Simons or Jerami Grant. Simons is going to have to learn how to deal with double and triple teams just as his mentor Lillard did.
When Simons is on, he’s a special kind of offensive threat. His athleticism, decision making and outrageous shooting ability gives him the tools to become an offensive powerhouse. Whether Simons makes an All Star game remains to be seen but the possibility is no longer a ridiculous suggestion.
Among combo guards, Simons is hitting 38.3 percent of threes on a ridiculous 8.5 attempts a game. He’s making 40.3 percent of his shots from more than 25 feet out on 6.1 attempts a game.
2023-24 Stats: 28.1 mins, 12.5 points, 29.9% 3pt on 4.1 attempts, 3.1 boards, 4.9 assists, 0.6 steals
I’m not worried about Henderson’s development. He hasn’t made as large a contribution as rookies such as Victor Wembanyama, Jaime Jaquez Jr. or Chet Holmgren, but that’s fine.
What’s more concerning is his two years with the G League Ignite and that franchise’s ability to prepare players for the NBA. The likes of Jonathan Kuminga, Dyson Daniels, Jalen Green and Jaden Hardy were all billed as relatively NBA-ready prospects, but all have taken their time to acclimate to the NBA game.
Having said that, this does not mean Henderson will not reach the heights he was initially pegged to get to. He still has the size, speed, skill set and work ethic that will ensure he succeeds in the NBA. He just needs more time to realize it.
The one thing we do know is that he probably won’t reach Simons’ level as a shooter. The ability to get the shot off both quickly and accurately from real range is a skill only a few players can boast. The stroke needs work, but it’s not broken and his ability to catch and shoot is there.
Among point guards, Henderson ranks 18th in assist rate and 23rd in block rate. His shooting splits of 36.1 percent from the field, 29.9 percent from three and 74.0 percent from the charity stripe are below ideal but I have full confidence this will improve.
When does the decision need to be made?
Henderson is in the first year of a four-year rookie-scale deal. If by the end of those four years, the Blazers want to retain his services they can re-sign him via restricted free agency.
Simons has served out his rookie-scale deal, earning a lucrative four-year, $100 million deal during the summer of 2022. The money was both team and Simons-friendly, particularly given his output over the past 18 months. He’s arguably outperforming this deal, which will look even better in 2026 when the salary cap has risen further.
By July 2025, the Blazers may need to start thinking about extending Simons for fear of him walking the following summer for nothing in return.
The team is also unlikely to be particularly good before the start of the 2025-26 season. That’s 18 months of losing records. It’s also 18 months for General Manager Joe Cronin to figure out what he’s got, for Henderson to become comfortable on an NBA court and to find out how good Simons can actually be.
There’s also the 2025 NBA Draft to consider. While this year’s class isn’t projected as a particularly talented group, the following draft is expected to be considerably better with talented forward Cooper Flagg up for grabs.
Another year with high lottery odds might be hard to stomach for the Portland faithful, but if the prize is a potential generational talent, it could be worth it.
What kind of point guard do you want?
Simons is very much Damian Lillard’s understudy. His ability to score at all three levels, facilitate at a league average rate while playing little-to-no defense makes him a familiar prospect.
Henderson is a more cerebral, pass-first proposition, with the potential to play above average defense at the guard position. The Georgia product will probably never be the shooter Lillard or Simons are, but that may not necessarily be required.
Why? I hear you ask. Because of Shaedon Sharpe. The Canadian’s ability to shoulder a lot of the scoring load takes a considerable pressure off of Henderson. Unlike the years of Lillard and CJ McCollum playing “your turn, my turn”, Henderson’s passing ability means he’s able to optimize Sharpe and co, making the offense a little less predictable.
If I'm right, Chauncey Billups will probably alternate between Henderson and Sharpe starting alongside Simons over the next 18 months. While Simons and Sharpe make more sense together, the Blazers will also need to ensure they have as much information as possible when it comes time to make a decision.
The decision is unlikely to be made before next month’s trade deadline, the 2024 offseason or the 2025 trade deadline. But the Blazers can afford to take their time with a young group and the 2025 summer when an enticing draft class emerges and decisions about a Simons extension start to be considered.
The Blazers should not be prioritizing wins and loses over the next season and a half. Deciding how high Simons can rise and who Henderson actually is will be key to what the backcourt looks like over the next decade.