2023 NBA Draft: After selecting Scoot Henderson, what's next for the Trail Blazers and Damian Lillard?

The moment the Portland Trail Blazers selected top point guard prospect Scoot Henderson with the No. 3 overall pick in Thursday night's 2023 NBA Draft — and even before then — questions arose about whether seven-time All-Star Damian Lillard would finally request a trade from the only franchise he has ever known.

"I'm told a timeline for where the future will land with Damian Lillard likely extends now between this point tonight to the start of free agency and potentially into free agency," Stadium's Shams Charania reported at the end of the first round, "just seeing exactly what Portland is able to do. And if Portland is unable to make a meaningful move enough to improve the team, Lillard has made it clear behind the scenes, from what I'm told, also publicly, that he doesn't want to come back into a rebuilding situation with young players."

Likewise, TNT and Bleacher Report's Chris Haynes reported "Lillard has not had any recent communication with the Blazers involving the draft, free agency or his future." He has, however, been in contact with Henderson.

"Our relationship is gonna grow, especially that I’m going there now," Henderson told SiriusXM NBA Radio. "I think our games pretty much complement each other. I get in the paint and spray it out, and I can play defense as well, and the things he does are obviously magnificent. I think we’re gonna do great. ...

"I think he should stay. I think it would be great to play alongside a guy like Dame, learning so much, especially how he came in the game so confident and fearless. I’m gonna take that same approach.”

The Blazers did not intend to trade the No. 3 pick unless it netted "one of a select number of premium targets," according to Yahoo Sports' Jake Fischer. Variousreportslinked Portland to Zion Williamson, Paul George, Mikal Bridges and Bam Adebayo, among others, but none of those rumors have come to fruition.

The well of potentially available stars who could elevate a Lillard-led roster in Portland to contention runs dry awfully quick, even if you include some of those aforementioned names. Jaylen Brown is not putting the Blazers over the top. They have 24-year-old Anfernee Simons, 20-year-old Shaedon Sharpe, the 19-year-old Henderson and multiple future first-round picks to offer in pursuit of multiple win-now upgrades, but it would make just as much sense, if not more, to build around them as the foundation of a future contender.

Lillard entertained several hypothetical trade scenarios on Showtime's "The Last Stand Podcast" earlier this month. When asked if he might prefer to land on the Boston Celtics, Brooklyn Nets, Miami Heat or New York Knicks, Lillard cited the Heat and Nets, given his relationships with Adebayo and Bridges and both teams' roster construction. That would explain a Portland pursuit of either player. It might also explain why Miami and Brooklyn would not entertain overtures for either player, considering Lillard may come to them.

After all, Lillard has gone on the record with his disinterest in a rebuild.

"That’s not what I’m interested in," Lillard told reporters in Los Angeles after a seventh straight loss in March. "That’s the frustrating part of it is talking about, 'Oh, you know, what’s going to happen next season?' and us building. Like, that’s not what I’m here to do, especially at this stage in my career. So, as much as it is encouraging to promote that brand of basketball that you probably win with going forward — and that’s what we've got to learn to make a habit of — right now I’m not out there looking like, OK, we're making these plays. This is what we've got to start doing. It’s hard for me to remove myself from the present as far as that, and then go forward about being excited about what we’re doing that we can do going forward."

Both Haynes and ESPN's Brian Windhorst have indicated in recent days that Lillard's stance on a youth movement is unchanged, even as he publicly stated that he expects to start next season on the Blazers.

Lillard turns 33 years old next month. A year removed from the most serious injury of his 11-year tenure in Portland, an abdominal tear that cost him 53 games, he enjoyed a career year this past season, averaging 32.2 points (on 46/37/91 shooting splits), 7.3 assists and 4.8 rebounds in 36.2 minutes a night for a 33-win team, making the All-NBA roster for a seventh time. How much longer he can maintain that level is a real question and one that would require the young Blazers to expedite their ascent if they hope to contend.

Even then, the roster is imbalanced. Lillard, Henderson and Simons are all 6-foot-3 or shorter, and Lillard's previous partnership with the 6-3 C.J. McCollum ended in a single Western Conference finals appearance. This is not a team one move or one leap from a title. They are bounds from Lillard's goal, even if they manage to re-sign free-agent wing Jerami Grant to a contract that will push them closer to the luxury tax.

So, here we are, the Blazers so far resistant to trading their best young players or Lillard, and Lillard so far resistant to teaming with young players or requesting a trade. Something has to give, and NBA front offices are awaiting the moment it does, because everyone knows Portland is in dire need of choosing a direction.