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Questions Arise About How Far Damian Lillard Can Carry Blazers

John Hollinger takes the Trail Blazers to task for their front office strategy.

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Portland Trail Blazers v Los Angeles Clippers Photo by Alika Jenner/Getty Images

Damian Lillard leading the Portland Trail Blazers back to playoff contention in a crowded Western Conference is not a consensus sentiment among NBA media. A 32-year-old Lillard has willed Rip City to relevance since 2014, but unanswered rotational questions and contract situations paint doubt in the minds of those looking at Portland’s prospects this season.

John Hollinger of The Athletic went in depth on Portland’s transactional ebbs-and-flows, which in his mind, have mostly neutralized each other to leave the Blazers in a “muddle in the middle.” On one hand, after a roster reshuffling, Hollinger wrote the Blazers are in a better spot than this time last year. Jerami Grant, Gary Payton II and Josh Hart are all legitimate additions and an expensive payroll last season made change necessary. But on the other hand, Hollinger offered one key critique to Portland’s “retooling” process.

In fact, if there’s a major criticism to be had of Portland’s approach, it’s that the Blazers didn’t go far enough. Portland tried to push its chips in after making the conference finals in 2019, and it didn’t quite work. It was long past time to admit this.

The obvious domino here is Lillard. Portland could have traded him for a king’s ransom a year ago but tried to bring back the band one more time. This offseason the Blazers tacked further into the wind by inking him to a two-year, $122 million extension that will pay him a staggering $63 million when he’s 36 in 2026-27.

The financial books are better than they were a season ago for the Blazers. Still, they’re over the association’s salary cap by an excess of $27 million for this upcoming trip around the NBA sun with not much flexibility in sight. This will stymie Portland’s ability in the offseason to make more moves to improve the roster, particularly on defense — a point Hollinger was sure to highlight — which has finished bottom three in the league the last three seasons. Even with the additions of Grant and Payton, he called the Lillard/Simons backcourt “even more vulnerable” on defense than the Lillard/McCollum iteration.

If Portland wants to rise above the middle, Hollinger wrote their success is largely contingent upon their young and burgeoning talent taking the next step, spearheaded by Anfernee Simons, Nasir Little and Shaedon Sharpe. Usurping “quick April cameo” forecasts will command a unified front on both ends, and elevated play from the youngsters.