Damian Lillard requested a trade from the Portland Trail Blazers in 2023. It was long overdue.
Lillard had already spent 11 years with the same franchise -- an eternity in today's NBA. But despite his individual success as arguably the best player Portland has ever had, Lillard never experienced team success, at least at the highest level. Seven All-Star seasons with the Blazers resulted in just one Conference Finals appearance, where they ultimately got swept by the Golden State Warriors in 2019.
Lillard was patient. He was loyal. Everything a team could ask for from the face of their franchise. He was also 32.
Lillard's championship window was closing. While his legacy goes far beyond a ring, it became clear that a title wasn't happening anytime soon in Portland. The Blazers finished the 2022-23 season with a 33-49 record. And although they questionably brought back Jerami Grant on a massive deal to fit with Lillard, it was clear that the veteran timeline was no longer the main priority. Instead of trading the No. 3 overall pick to get Lillard win-now help, they decided to draft his successor in point guard Scoot Henderson.
Blazers' new core faces same limited ceiling problems
Seeing Lillard in a different team's jersey felt very off, like an alternate timeline that wasn't supposed to happen. But from Portland's perspective, it was the right decision to prioritize their youth movement with top ten picks Shaedon Sharpe and Henderson rather than Lillard's timeline. Portland experienced regular-season success during Lillard's first stint, but it was apparent that its roster had a limited playoff ceiling. They needed a fresh start.
This time around, Portland's roster construction seems much better equipped for eventual postseason success. Their previous formula of being led by undersized, offensive-minded guards didn't translate well when it mattered most. Now, they are reversing that identity, building a team around their defense, size, and athleticism with frontcourt players like Deni Avdija, Toumani Camara, and Donovan Clingan as their core pieces.
However, the issue with this approach is Portland's lack of star power.
Avdija was a steal, but he's ideally a tertiary option on a championship team. Henderson and Sharpe have shown flashes of that upside but remain inconsistent. The Blazers needed patience in their approach until they found a true north star to guide their rebuild. Instead, they're accelerating too soon before knowing they even have that piece on their roster.
The draft is the best way to add that player, especially for a market like Portland. Yet Portland keeps taking one step forward and two steps back with win-now moves like trading for Jrue Holiday and his three-year, $104 million contract. That will help compete for a play-in spot this season, but at the expense of their long-term outlook and the championship goals they should be pursuing.
Let's hope Henderson or Sharpe break out, or Yang Hansen turns out to be a star, because it will only get harder for Portland to raise its ceiling.