Four years ago, the Portland Trail Blazers stamped their first Western Conference Finals appearance since 1999-00. In the ensuing seasons, they’ve twice bowed out of the first round and twice failed to make the playoffs altogether. The past two years have seen them earn the seventh overall pick and third overall pick, a pair of shiny lottery selections netting them quite the intriguing young duo in Shaedon Sharpe and Scoot Henderson. Joining this budding, wide-eyed core is Anfernee Simons, a 24-year-old shooting guard who averaged 21.1 points (58.1 percent true shooting) and 4.1 assists per game in 2022-23.
The downswing of these floundering campaigns for Portland appears to be franchise pillar Damian Lillard feeling as split as ever about his future with the organization. Between his own words and the words of credible reporters, it’s evident the soon-to-be 33-year-old does not want to be involved with a youth movement and prefers to be flanked alongside veterans who can help optimize his prime and the Blazers’ chances of winning.
On Monday, The Athletic’s Sam Amick detailed the narrow path Portland can venture “for him to be content with the Trail Blazers’ state of affairs heading into next season,” which could feature “a dream scenario” of retaining Jerami Grant and finding a way to land Draymond Green in free agency. Amick didn’t report that Lillard already has a foot out the door or anything, but conveyed the tenuous tightrope Portland must walk in the coming weeks to ensure its vision is aligned with his preferences. Hours later, Bleacher Report’s Chris Haynes tweeted that Lillard and his agent, Aaron Goodwin, would meet with the team on Monday “to discuss the franchise’s direction.”
After that meeting, Blazers general manager Joe Cronin said he, Lillard, and Goodwin “had a great dialogue. We remain committed to building a winner around Dame.” Brian Windhorst of ESPN noted that Lillard hasn’t requested a trade, but made clear to note that Portland isn’t fully out of the woods yet, as Lillard plans to take a wait and see approach to free agency.
Regardless of how one feels about them dealing Lillard, the possibility seems as plausible as it’s been since he began his stay in the Rose City 11 years ago, despite the organization’s public commitment to him. I’m not here to advocate for or against trading Lillard. Whatever decision those involve here land on will be theirs to embrace and navigate. But if a move does materialize, Portland is fairly well-positioned to launch into a rebuild behind Henderson, Sharpe, and Simons, three tremendously talented perimeter players yet to reach their primes.
That’s not to say they’ll smooth over immediate repercussions of Lillard’s departure, an All-NBA superstar who has helped the Blazers punch above their weight numerous times during his tenure. There would be at least a season or two filled with lots of struggles and a focus on development. That development is worth investing in, though, because of what would remain if Lillard exits.
Simons is the most established among the three potential bedrocks. Midway through 2021-22, he became a starter and has flourished with his versatile scoring. He’s an intrepid, dynamite gunner with a hairpin trigger, burying 39.7 percent of his long balls the past three years and doing so in motion, off the bounce, and stationary. Last season, he cashed in 39.2 percent of his catch-and-shoot triples and 35.5 percent of his pull-up bombs. There are few players around the league more potent and malleable beyond the arc than Simons — one of them, funny enough, might be Lillard.
What’s really amplified Simons’ ascent is his growth as an interior scorer, which not only progressed between 2021-22 and 2022-23, but throughout 2022-23. During his first four years in the league, he shot 46.3 percent on twos, including 57.3 percent at the rim, per Cleaning The Glass. Last year, he shot 52.8 percent on twos, including 65 percent at the rim (65th percentile among combo guards). He endures contact more seamlessly. He holsters creative finishes around the basket to exhibit his deft touch. He’s not confined to long-range looks and hurried midrange pull-ups like he was earlier in his career. There’s better pacing in his ball-screens.
Simons turned 24 two weeks ago. He’s taken significant leaps each of the past three years to emerge as a versatile secondary ball-handler and elite shooter; that’s a good player worth prioritizing. If the Blazers pivot toward a Lillard-less life, he should be among the most prominent reasons for optimism. As Simons walks into his peak seasons, the goal will be to round out the periphery of his game: broader, hastier passing reads, sustained refinement as a finisher, and continued defensive improvement.
Meanwhile, his contemporaries headlining Portland’s 24-and-under cast, Henderson and Sharpe, are more like blank canvasses of potential. The former’s yet to grace an NBA floor. The latter’s logged just fewer than 1,800 minutes in the Association. Who they become is harder to gauge, but the allure stems from who they’ve been in the direct backdrop to their futures ahead.
As a rookie, Sharpe instantly slotted into a reserve role and delighted with his spot-up shooting, finishing, and keen off-ball movement. He shot 67 percent at the hoop (69th percentile) and drilled 45.5 percent of his catch-and-shoot threes. Late in the year, with Lillard and Simons sidelined and Portland’s playoff intentions extinguished, he assumed a grander on-ball gig, averaging 23.1 points (57.4 percent true shooting), 6.1 rebounds, and 4.1 assists over his final 10 games.
The relevance of those flashes in a stretch when Portland was routinely routed is yet to be determined, of course. But the 6’6 wing who was a top-5 recruit in the country hinted at latent off-the-bounce verve and wily drives punctuated by trampoline, locomotive finishing. The key will be streamlining those on-ball reps into consistent production and adding some playmaking to complement his scoring acumen. Sharpe shot 25 percent on pull-up threes and 41.3 percent on pull-up twos. According to PBPStats, his effective field goal percentage on assisted buckets was 63.8 percent, while his effective field goal percentage on self-created shots was 44.8 percent.
He’s already a multifaceted play-finisher who would benefit from a runway to explore the scope of his creation ceiling. He might rumble over a few mailboxes and rough up some lawns as he test-drives a new environment, but those are exactly the sort of blemishes a rebuilding space invites, if one were to arise in Portland. Sharpe will be 20 for his entire sophomore season, is flexible and a pogo-stick in sneakers, as well as a good shooter and a shrewd cutter. The foundation of a rockstar off-ball scorer exists, with the hope that it’s merely a baseline and the imminent seasons before him lead to much more.
The likelihood of Simons or Sharpe reaching premier initiator status is a bit lofty, though that shouldn’t diminish the excitement around their prospects. Fortunately, Henderson can be that, anchored by his prestigious athletic profile and ball-screen bravado. Henderson commandeers pick-and-rolls with the cadence, manipulation and decision-making of star NBA guards, not a 19-year-old readying for his first Summer League cameo next month. He puts big man defenders in conflict, properly times his pocket passes or kickouts, knows how to exploit weakside helpers, and is adept creating space for his own looks. When he and G League Ignite squared off against Victor Wembanyama and Boulogne-Levallois Metropolitans 92 in October, Henderson’s ball-screen wizardry — amplified by his athletic tools — was a sight to behold.
His 0-60 burst, change-of-direction, and vertical explosiveness are tremendous. The manner in which he blends speeds to perplex defenses is clinical. He can chisel through dudes without smashing the gas pedal and risking erratic drives. He’ll shake free of swarming limbs by stopping on a dime or dialing up the accelerator; both are viable options and underscore his standout physical traits. He’s an NBA-ready athlete and processor who could be the centerpiece of a high-level offense in his prime, or even sooner.
With Simons, Sharpe, and Henderson all presumably best at the 1 or 2, worries of positional overlap and diminishing returns begin. A redux of building around guards, a la Lillard and C.J. McCollum, pops up, too. Those Lillard-McCollum squads fell short because McCollum didn’t prove a consistent co-star, along with sporadic wing and center play, not because of which positions Portland designated as pillars. The beauty of these three is their harmonic repertoires. They’ll spearhead great teams if they rise to that level enough, independent of position, and are surrounded by a group that augments them.
Simons and Sharpe are good-to-great floor-spacers. Henderson is working to stretch his range (30.2 percent from deep last season). Sharpe and Henderson pressure the rim. Simons is working to carry forward his 2022-23 improvements as a slasher. Simons and Henderson are accomplished creators. Sharpe is working toward that.
All three can accommodate a lead ball-handler. Henderson garners a misguided ball-dominant label in some crowds, but is a good cutter, is comfortable around dribble handoffs, and began many possessions away from the action with Ignite. He is a useful off-ball cog and far from a non-factor. This team would also have time to discern who the ideal backcourt pairing is. Heck, maybe, Sharpe at 6’6 with a 7-foot wingspan ends up being a 3 and his formative years reveal that the trio is functional together. A rebuild would present opportunities to learn whether they are, with fewer worries about impending win-loss results.
None of this even mentions the haul the Blazers would accrue for Lillard if that’s the direction they go. They would receive various first-round picks, even if it’s perhaps not as many as they or their fans seek in return for Lillard. The launching point is not solely Simons, Sharpe, and Henderson, which is a pretty good spot if it were. Between those from their hypothetical trade partner and their own, they would wield a slew of firsts to land complementary players around their youthful triad. They would be unburdened by win-now rigors, a pressurized necessity borne from the luxury of rostering someone as incredible as Lillard.
The Blazers might make some tweaks that appease Lillard and aim to return to the playoffs in a crowded Western Conference. They also might be maneuvering without him in the fold for the first time in a long time and have their eyes fixated away from the 2024 playoffs. If they do, hope still exists, despite the understandable melancholy a post-Lillard reality may inspire for fans. There is promise on the horizon, all the while acknowledging the challenging path awaiting them. That promise is a ship captained by Anfernee Simons, Shaedon Sharpe, and Scoot Henderson.
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