Blazers projected lineup and rotations heading into 2023-24 season

The Portland Trail Blazers spent all summer half-trying to convince Damian Lillard to stay. The team spent $160 million to keep Jerami Grant around. That's a win-now move. Crucially, however, the Blazers also kept the No. 3 pick in June's NBA Draft and used it on Scoot Henderson, a point guard.

That was the turning point. Lillard requested a trade to Miami before fans even had time to celebrate Henderson. Since then, it has been months of stony silence, with Lillard refusing to openly criticize the organization and the Blazers refusing to stoop to the level of Miami's shoddy trade package.

With just over a month until training camp, one of two things will happen: Portland will get serious about trading Lillard, probably to Miami, or the Blazers will ask Lillard to report to camp. Aaron J. Fentress of the Oregonian reports that Lillard "would show up" if Portland doesn't strike a deal before the start of camp on Oct. 3.

That could get awkward fast, but Joe Cronin and the Blazers front office have projected an image of strength in this time of great turmoil. The Blazers aren't going to send away their franchise pillar for a bag of candy. It will require an offer legitimately in line with Lillard's value as a top-20 NBA player.

If Lillard sticks around, then the team will try to win as many games as possible and hope against hope to restore the relationship. Lillard has a deep love for the Portland community and he has been a prophet of his own loyalty to the Blazers for the last decade. If any star and team can actually build back trust and find harmony, it's probably these two.

If Lillard doesn't stick around, then it will be full-on tank season for Portland. The Blazers have a fantastic foundation with Henderson, Anfernee Simons, and Shaedon Sharpe, but Portland won't win many games without Lillard. Time to Flunk for Flagg, or something like that.

Chauncey Billups hasn't reached the point of a hot seat, but his performance as Portland's head coach has been a matter of debate pretty much since day one. If the Blazers truly embark on a rebuild, one has to imagine Billups' future with the team would come into sharper focus as the front office attempts to build the right team with the right habits for winning down the road.

Here's what the Blazers are working with rotationally.

Portland Trail Blazers starting point guard: Damian Lillard

There's a reason the Blazers don't really want to trade Lillard. The front office made the best choice for the franchise in selecting Henderson on draft night, but that move was not meant as a rebuke of Lillard. Portland has a lot of guards on the roster, but there's every reason to believe Henderson and Lillard would (or will) function well together.

Last season was the best individual campaign of Lillard's remarkable career. He averaged 32.2 points, 4.8 rebounds, and 7.3 assists on .463/.371/.914 splits in 36.3 minutes. Long commended for his deadly pull-up jumper and endless 3-point range, the overarching breadth of Lillard's talent tends to get underrated. He's an effective slasher with a spritely first step and the playmaking acumen to pick apart overzealous defenses.

Even as Lillard ages, he should be able to maintain elite production because of his shooting and basketball I.Q. He can stick a jumper over any defender with quick, compact mechanics. His shot versatility should lead to productive off-ball work if Lillard ever commits to a more diverse approach. He's ball-dominant right now, but in a magical alternate timeline where the Blazers get to keep Lillard, Henderson is the perfect playmaker to age into stardom as Lillard ages out of his prime and into a more complementary role.

The defense remains a point of concern for Lillard, who is 6-foot-3 and not particularly determined to get stops. That's in part due to the size of his offensive burden in recent years. From a basic preservation statement, it's probably smart for Lillard to get in reps with other ball-handlers for that reason too. Maybe Henderson would allow Lillard to expend more effort on the defensive end.

At the end of the day, however, Lillard's probably on his way out the door. Probably sooner than later.

Primary backup point guard: Scoot Henderson

Scoot Henderson will start sooner than later, whether it's in place of Lillard or (more improbably) beside Lillard. The Blazers could have appeased a publicly restless Lillard by trading the No. 3 pick, but there was simply no way to recoup value similar to Henderson. He's a future face of the franchise and one of the best point guard prospects in recent memory.

The "No. 3 pick" label will probably lead to Henderson being underrated. This was an especially talented draft class, especially at the top. Henderson would have been the No.1 pick in a more standard draft class. Take 2022's class, for example. Chet Holmgren and Paolo Banchero were unique, intriguing prospects, but neither reaches the same heights as Henderson as a prospect.

At 6-foot-3, Henderson is blessed with the strength of professional MMA fighter. He can absorb contact and dish out punishment in a way few teenaged point guards can. Put a slighter guard in Henderson's path and he can bully his way to the rim. Combat his strength with a burlier wing, and Henderson's deadly first step and quick-twitch athleticism will make life extremely difficult on the opposition.

Henderson battled inefficiency with the G-League Ignite, but he's a competent three-level scorer. His pull-up jumper is money from mid-range and there's every reason to believe his 3-point shooting will follow suit. Sharing the court with other quality guards could do Henderson a lot of good. Station him away from the ball, and he's still going to wreak havoc as a slasher and connective playmaker.

Other players who could receive minutes at point guard: Anfernee Simons