The Portland Trail Blazers will look much different whenever the front office finally pulls the trigger on a trade for Damian Lillard. Even if the greatest player in franchise history takes his talents to the Miami Heat, though, Portland's backcourt logjam is poised to remain in place.
It's no secret the Blazers want to move Tyler Herro to a third team should the former Sixth Man of the Year be included in a blockbuster trade for Lillard. Any other young perimeter player who finds himself as the centerpiece of a Lillard trade if Portland opts against making a deal with Miami almost surely won't be playing for Chauncey Billups, either.
Lillard can say all he wants about his support of the Blazers taking Scoot Henderson with the No. 3 overall pick in the 2023 NBA Draft. But Henderson's presence bolded and underlined writing already on the wall about Lillard's future in Rip City, and not just because Portland clearly drafted his heir apparent as franchise floor general. After selecting Shaedon Sharpe with the seventh overall pick in last year's draft, the Blazers were stacked at guard even before bringing in Henderson.
Chauncey Billups will have some tough lineup decisions to make this season no matter where Lillard is ultimately traded. At least general manager Joe Cronin seems dead set on avoiding the cardinal sin of Portland's previous front office regime, completely uninterested in making the core of his in-flux roster smaller and more guard-heavy than it already is.
As Cronin and company work the phones to drive up Lillard's trade price, here's the one Blazers player in danger of losing his starting job in training camp.
Blazers player in danger of losing starting job in 2023-24: Anfernee Simons
Billups has been even more outspoken than Cronin about the need for Portland to deploy bigger, more defense-oriented lineups. He was sounding that alarm just a couple weeks into his first season on the sidelines, when the Blazers were starting C.J. McCollum and Norman Powell next to Lillard, none of whom stand taller than 6'3.
Shaedon Sharpe has more length and athletic pop than those guys, but don't expect Billups to make a similar mistake in 2023-24 by deploying all three of Portland's top prospects as starters. The backcourt of Lillard and McCollum never took the Blazers further than a sweep in the Western Conference Finals. It's woefully naive to believe the starting tandem of Henderson and Simons would ever yield that much success, let alone lead Portland to its first NBA Finals appearance since 1990.
Henderson is basically what Lillard's been for the Blazers the last decade-plus. With his predecessor gone, the 19-year-old is a shoo-in starter at point guard as a rookie. Sharpe's ceiling as a hyper-athletic bucket-getter and secondary creator with the size to guard small wings might be just as high as Henderson's. This team's eyes pointed squarely toward the future, it'd be a major mistake to prioritize immediate competitiveness by playing Henderson and Sharpe alongside another guard.
There's no guaranteeing a starting lineup featuring Henderson, Simons and Sharpe would be Portland's best anyway. Diminishing offensive returns are always a risk when deploying ball-dominant, offense-first guards simultaneously, and it's not like the Blazers possess much scoring punch off the bench. No team in the league knows how difficult it is to construct a worthwhile defense around two small guards better than Portland.
Matisse Thybulle is back this season after the Blazers matched the three-year, $33 million offer sheet he signed with the Dallas Mavericks in free agency, too. He might be more of an off-ball disruptor than point-of-attack stopper, but is still a viable top defender of opposing ball handlers. Maybe Henderson and Sharpe evolve into plus defenders down the line, but Simons—entering his sixth season—is nowhere near that llevel.
With Thybulle, Jerami Grant and a center to be named, at least Portland can muster the type of lineup construction their blue-chip prospects could ride to contention whenever Henderson and Sharpe approach their primes. Simons has more juice as a playmaker than his shoot-first reputation suggests, but the book has closed on his hopeful development into a full-time point guard absent absolutely ideal roster circumstances surrounding him. It's probably time for Simons to embrace his destiny as a souped-up, sweet-shooting sixth man, a la Lou Williams.
Then there's the possibility of Portland trading Simons to better balance the roster and increase its long-term flexibility once the front office finally bites the bullet on Lillard. Henderson and Sharpe are untouchable for now. Simons just doesn't own that distinction, perhaps the most significant of many reasons he seems bound to revert back to the bench in 2023-24 after starting every game he played a year ago.