Damian Lillard is the greatest player in Portland Trail Blazers history. He's made six All-NBA teams, played in six All-Star Games, won Rookie of the Year and earned a gold medal with Team USA at the Beijing Olympics. The unique space Lillard occupies in NBA culture might be as impressive as any of those accomplishments. He's one of the most respected players in basketball, by teammates, playing peers and fans alike, with a crunch-time reputation more feared than any player's in recent memory outside those of Michael Jordan and Kobe Bryant.
Lillard, obviously, is already NBA royalty, and is still in the thick of his prime at 31. He's not finished racking up accolades and continuing to cement his place in the game. No matter what achieves from here, though, it's clear that being named one of the 75 greatest players of all time will rank very high on Lillard's personal list of triumphs.
“It’s a special honor, probably the best honor of my career so far to be considered one of the 75 best in a 75-year history,” he said, per the Blazers' Casey Holdahl. “That’s a hell of an accomplishment, a hell of an honor. And I'm still playing.”
Whether Lillard is more deserving of a spot on the league's 75th-anniversary squad than Dwight Howard, everyone's favorite snub, is debatable. What's definitely not is that Lillard, nine years into his career, remains the exceedingly rare caliber of player around which a championship team can be built. Ask Howard just how fleeting time spent toward the very top of the league's individual hierarchy can be.
It's a testament to Lillard's talent, work ethic and personality that he's still there, providing Portland just enough hope for an underdog title run and the rest of the league endless fodder for how far he could take another team while playing next to a fellow superstar. For the foreseeable future, at least, that latter dynamic will amount to nothing more than rank speculation.
There have been no signs pointing to Lillard's possible exit from Rip City since mid-July, when he forcefully pushed back against reports of an imminent trade request. All momentum suggesting he'd play at least one more season with the Blazers was further fortified earlier this week, Lillard waxing poetic about “not leaving Portland” in large part because of his unique connection with Chauncey Billups. As has been clear for months, Lillard isn't going anywhere this season.
But just because he's recommitted to the Blazers hardly means management should shrug off the sense of urgency Lillard demanded over the summer. There's an organizational obligation that comes with employing one of the 75 greatest players ever in his prime. Olshey, clearly, believes he and the front office lived up to it and Lillard's associated pleas by replacing Terry Stotts with Billups and remaking a bench that doomed Portland in its disheartening first-round loss to the Denver Nuggets last season.
As much doubt exists about Olshey's interest in ever moving C.J. McCollum for anything less than an objectively winning return, the Blazers have been regularly mentioned as teams in discussions with the Philadelphia 76ers about Ben Simmons. There's at least some allowance from management for the possibility that Portland isn't good enough to win a title as currently constructed.
Maybe the Blazers' ugly performance in exhibition play and the season-opener prove anomalous, and they quickly acclimate to Billups' schemes to emerge as a real threat in a wide-open West this season. It's not impossible. But that best outcome is still a major longshot, and unless substantial progress just below that level comes to pass, Portland must be ready to undergo the roster overhaul Lillard called for in the offseason come next summer—or in a doomsday scenario, even before the trade deadline.
Jusuf Nurkic's contract expires after 2021-22, and so does Robert Covington's. Portland currently has just six players under contract for next season, not including prospective restricted free agent Anfernee Simons. If there's ever an opportune time to blow up the Blazers' core, basically, it's before 2022-23, when they'll have to vault well past the luxury tax to retain Nurkic and Covington on pricey new contracts or let them walk in free agency. Barring a career-best campaign that portends his game aging gracefully, this season could mark the peak of McCollum's trade value, too.
There's no indication—well, other than recent history—Portland will be satisfied if the status quo fails again. Lillard surely wouldn't express such newfound confidence in his team's direction if he didn't believe the Blazers were fully committed to his ultimate goal of winning at the highest level. Indeed, at Media Day both Olshey and Billups alluded to embracing the urgency Lillard pushed on them with his public wavering.
Here's hoping Portland doesn't run from it now that the opportunity exists. One of the 75 best NBA players ever deserves much better than that, just like Lillard did before he threatened to leave Rip City last summer.
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