Questions about whether seven-time All-Star Damian Lillard would finally ask to be traded from the only team he has ever known surfaced even before the Portland Trail Blazers selected top point guard prospect Scoot Henderson with the No. 3 overall pick in Thursday night's 2023 NBA Draft.
After the first round, Shams Charania of Stadium observed, "Just seeing exactly what Portland is able to do, a timeline for where the future will go with Damian Lillard certainly extends now from this point tonight to the start of free agency and perhaps into free agency. Additionally, Lillard has made it known publicly and informally that he does not want to return to a rebuilding phase with young players if Portland is unable to make a significant move sufficient to enhance the squad.
Similarly, according to Chris Haynes of Bleacher Report and TNT, "Lillard has not had any recent communication with the Blazers involving the draft, free agency, or his future." Henderson, however, has spoken with him.
Henderson told SiriusXM NBA Radio that "our relationship is going to grow," especially given that "I'm going there now." "I believe that our games work well together. I can play defense as well as get into the paint and spray it out, and the things he does are unquestionably amazing. I believe we'll succeed admirably.
"I believe he should remain. I believe it would be amazing to play with someone like Dame and learn from him, especially given how he entered the game with such assurance and bravery. I'm going to use the same strategy.
According to Jake Fischer of Yahoo Sports, the Blazers had no intention of dealing the third overall pick unless it resulted in "one of a select number of premium targets." Zion Williamson, Paul George, Mikal Bridges, and Bam Adebayo were among the players Portland was reportedly linked to, but none of those speculations have materialized.
Even if you consider some of those players, the pool of prospective free agents who could propel a Lillard-led team in Portland into contention runs out rather quickly. The Blazers are not winning because of Jaylen Brown. They can pursue several win-now upgrades with the 24-year-old Anfernee Simons, the 20-year-old Shaedon Sharpe, the 19-year-old Henderson, and multiple potential first-round picks, but it would make just as much sense—if not more—to build around them as the cornerstone of a future contender.
On Showtime's "The Last Stand Podcast" earlier this month, Lillard entertained a number of speculative trade ideas. Given his connections to Adebayo and Bridges and the roster composition of both clubs, Lillard mentioned the Heat and Nets when asked which team he might choose to join among the Boston Celtics, Brooklyn Nets, Miami Heat, or New York Knicks. That could account for Portland's interest in either player. Given that Lillard would approach them, it might also help to understand why Miami and Brooklyn would not accept offers for either player.
After all, Lillard has publicly expressed his opposition to a rebuild.
After a seventh straight defeat in March, Lillard told reporters in Los Angeles, "That's not what I'm interested in. "That's the annoying part of it—talking about, 'Oh, you know, what's going to happen next season?' and our preparation. At this point in my career, specifically, that's not what I'm here to do. So, even though it is motivating to advocate for the style of basketball that you will likely win with moving forward — and that is what we need to learn to do regularly — at the moment I'm not out there acting like we're making these plays. This is the first thing we need to accomplish. It's challenging for me to go that far beyond the present and then to remain enthusiastic about what we're doing and what we can do in the future.
Haynes and ESPN's Brian Windhorst both said recently that Lillard's position on a youth movement is unchanged, despite the fact that he openly stated that he anticipates joining the Blazers to begin next season.
Next month, Lillard will turn 33 years old. He had 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 per night for a 33-win team, and making the All-NBA roster for the seventh time. His most serious injury during his 11-year stint in Portland was an abdominal tear that cost him 53 games. The young Blazers would need to speed up their ascension if they want to contend because it is doubtful how long he can keep at that level.
The roster is still unbalanced even then. All three players—Lillard, Henderson, and Simons—are 6 feet 3 inches or shorter, and Lillard's previous alliance with 6-3 C.J. McCollum resulted in just one trip to the Western Conference finals. This team is not one step or jump away from winning the championship. Even if they are successful in re-signing free agent wing Jerami Grant to a contract that will bring them closer to the luxury tax, they are still far from Lillard's objective.
So, here we are with the Blazers refusing to move their best young players or Lillard thus far, and Lillard refusing to team up with young players or ask for a trade thus far. NBA front offices are anticipating the time when something has to give since everyone is aware that Portland needs to make a decision quickly.