Could Anfernee Simons Actually Be The Answer At Point Guard?

Discussions surrounding how and when the Portland Trail Blazers trade Anfernee Simons have been building in recent months. Just last week, I wrote about the 25-year-old guard’s trade value and the type of package General Manager Joe Cronin might yield in return.

With his age, skillset and the 18 months remaining on his relatively reasonable deal, the Blazers starting point guard will likely be of interest to at least a handful of suitors.

For many, the moving of the former IMG Academy standout is a fait accompli. As such, he’s been bundled into conversations alongside Jerami Grant, Deandre Ayton and Robert Williams III, all of which don’t appear to be in Cronin’s long-term plans.

But what if we’re getting ahead of ourselves? While I never make big-picture statements on individual games, we saw his production and game winner against the Denver Nuggets last week. The outing was a reminder of a skillset that only Simons and a smallish percentage of players actually have on the offensive side of the ball.

I won’t deny he has his limitations, largely on defense, but Simons could be young and talented enough to consider holding onto.

How Did We Get Here?

The former 24th pick out of Florida’s IMG Academy experienced an under the radar NBA initiation. Outside a memorable 2018-19 game 82 win against the Sacramento Kings, the baby-faced Blazer saw little time his first couple of seasons.

He bided his time behind Damian Lillard, CJ McCollum and later Norman Powell before enjoying a little success in his fourth season. At the 2022 Trade Deadline, the Blazers dealt McCollum to the New Orleans Pelicans and Powell to the Los Angeles Clippers, purposefully opening up minutes for Simons.

His progression continued after Lillard was moved 15 months ago when Simons became the franchise’s first or second best player, depending on how you feel about Jerami Grant.

Over the past 24 months, Simons has shown an ability to score at all three levels, creating for himself and others, thanks to finely tuned instincts, accuracy and athleticism.

This Season

Through 27 games, Simons is down in almost all counting stats compared to his previous two seasons. He’s averaging 17.0 points on 32.0 percent from three and 40.8 percent front the field, 2.6 rebounds, 4.8 assists and 1.0 steals.

He’s still achieved his 30-plus point a game heights, but has failed to consistently produce at that level — I point to Thursday night’s dismal outing against the Utah Jazz.

I’m giving him the benefit of the doubt based on the past two seasons. He’s got a track record contributing as a scorer, starring as one of the NBA’s best three point shooters, not to mention a burgeoning ability to create for others.

The Blazers Backcourt

As I’ve said in previous columns, I’m not ready to right off Scoot Henderson as a starting level NBA point guard. But he’s probably not a cornerstone or All Star talent — two heights he’ll continue to be measured against thanks to those third-overall-pick-behind-Wembanyama expectations.

Almost 18 months into his career, it’s pretty clear the shooting, decision making and finishing aren’t quite there. He could still get there, but it becomes less likely with every passing month.

For me, a realistic outcome for Henderson is an Anfernee Simons-type contributor. Simons is obviously the better shooter and all-round scorer but Henderson may be the better the passer and floor general and perhaps a better defender.

If I’m right, why would the Blazers part with a still-young Simons for someone who might reach a similar level of production one day?

Wouldn’t they be better off with a backcourt of Simons and Sharpe who can both spread the floor and score in a multitude of ways? We’re only just starting to see the pair play extended minutes together and the sample data so far is an understated “intriguing”.

This eventuality would rely on Simons continuing to improve his facilitation and Sharpe being the defender his physical gifts should allow him to be. Two goals that aren’t completely unreasonable.

The 2025 NBA Draft

The Blazers will likely have a high draft pick in June. How high depends on May’s NBA Draft Lottery. But if the Blazers land a selection in the second and third pick range, then Rutgers point guard Dylan Harper may come up for discussion in the Blazers war room.

In theory, Harper projects as a better player than both Simons and Henderson. But if Henderson’s young career has taught us anything, it’s that theory and projection should be taken with a grain of salt.

The Contract Situation

A quick note here. Simons is currently extension eligible leading into his 2026 unrestricted free agency. If the Blazers are unsure about how they handle Simons’ future and decide not to trade him in the near future, they probably need to work on an extension next summer.

This will no doubt be a tricky negotiation but if they can somehow get him on similar money to the $25 million per annum he’s currently earning, it’s a win. This amount works on the Blazers payroll and also as a trade piece dangled in front of trade partners.

Will It Work?

I don’t envy Cronin. He’s faced with a number of tough decisions over the next 18 months as he attempts to push the roster from rebuild into feisty upstart. Henderson has been far from an overwhelming success and the uncertainty surrounding his revised ceiling has further complicated Cronin’s decision.

Simons isn’t a traditional point guard. His ability to create for others is a work in progress, but we’ve seen at different stages over the past three years, he has an aptitude for it. I’m also not convinced giving Henderson the starting job will change the way he impacts this team or winning. I could be wrong. But if I had to pick between the two right now, I’m in effuse favor of Simons.

Having said that, going down a path with Simons as the “numero uno,” uno presents its own challenges for Cronin as he continues to build this team.

With Simons at the point, this team needs above-average defense, length and creation at multiple positions to counter for the guard’s deficiencies. This means more guys like Deni Avdija who are rare and not particularly easy to acquire. This strategy also narrows the type of player the Blazers can go after.

The Blazers are still not competent enough to draft for position at the 2025 NBA Draft, particularly if their pick is high. So if Cooper Flagg is gone and Harper is sitting there you take the best player available and solve the point guard dilemma that way.

Simons could very well be traded over the next few weeks if Cronin identifies a deal where the package is more beneficial than holding onto the 25-year-old. But I would not put it past him to consider the Florida flamethrower as a longer term option if he shares my concerns about Henderson.

At the end of the day, I don’t think the Blazers have their answer at point guard, but Simons is definitely a better option right now.