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Damian Lillard May Have Hit The Eject Button Too Late

PORTLAND, OREGON - MARCH 24: Damian Lillard #0 of the Portland Trail Blazers watches from the bench during the second half against the Chicago Bulls at Moda Center on March 24, 2023 in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Soobum Im/Getty Images)
Soobum Im/Getty Images

There has rarely been a free agency quite like Damian Lillard's free agency, and that's saying something given the addiction we have for NBA owners burning money and players catching it before it turns to ash. Lillard's free agency has brought on a level of simultaneous scolding and cheering that has even been referenced retroactively, as though the decision he made to stay in Portland until just now is less about loyalty and purpose and more about pigheaded shortsightedness, and in either mindset there is a level of general disapproval that he didn't throw himself into the wind years ago.

By now, the hooper intelligentsia has matured in its coverage of free agency, although there are still some hesitancies about players who ask for "too many" trades—James Harden, Kyrie Irving, and Kevin Durant most notably. There are pointed questions and shrill finger-waggings about whether the player can ever find the athletic and competitive happiness he claims to seek, or the ring he is supposed to crave more than skin itself. That is Harden's current predicament, as his desire to leave Philadelphia is now compared to his desires to leave Houston and then Brooklyn and reminds us that in many eyes, player empowerment has distinct limits, like coaches’ challenges.

Lillard, though, has been badgered about not leaving soon enough, as though there is a window of loyalty that should never be either too open or too shut. And now that he has finally abandoned the notion that he can lift the Trail Blazers without more help than has been provided by two different general managers, he is getting more advice about what and where than any other player ever. Starting with, "Why didn't you do this three years ago?"

This is the price Lillard pays, apparently, for being the hot item on this summer's menu, with the notable exception that he is being passive-aggressively scolded for not having been the hot item two years ago. No other player has ever been propelled into the news cycle with the almost unanimous "What kept you?" he is getting now, in part because Portland isn't considered cool enough in NBA terms to have a player like Lillard, and hasn't been cool enough since Bill Walton roamed the earth in the days when the NBA itself wasn't cool enough.

The nuts and bolts of the story is that Lillard wants Miami, but Miami may not have the right package to send back to Portland. He kind of likes San Antonio, but he would have to forgo the immediate gratification of a ring because the Spurs aren't perceived as close enough to title contention even with the new designated manchild Victor Wembanyama. Utah is being floated as a longshot because Danny Ainge hoards draft picks the way your grandmother hoards pictures of you as a baby. He could even get stuck in Portland if GM Joe Cronin insists on a commensurate return, in which case Lillard will be held responsible for waiting until the wrong summer to ask for this. 

This is the new level of post-dated expertise that makes NBA free agency the marvel it is. It is a debating mechanism that is always shifting—from the present (who's going now) to the future (who's available next year or the year after that) and now the past. There aren't a lot of other options for new ground, quite frankly, not if you still want to be tethered to the linear nature of time. Damian Lillard will either find his happiness, or have it modified or maybe even deferred, but no matter what, he will be held responsible for not knowing 2023 in 2021. The shame must just lap at his eyelids every day.

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