Damian Lillard Requesting a Trade From Portland Was the Only Inevitable Outcome

Both the Trail Blazers and the star guard will be better off parting ways.

For all the chest thumping coming out of Portland the last few weeks, all the plans to wheel and deal early in free agency, all the public statements declaring the Blazers' intention of building a winner around Damian Lillard, this was the only inevitable outcome.

Damian Lillard requesting a trade.

And Portland agreeing to accommodate him.

It’s a shame that Lillard had to request a trade, really. He didn’t want to. Lillard has given 11 years to Portland. He made seven All-Star teams. Seven All-NBA teams. He’s the greatest player in Blazers history. He shouldn’t have had to go to Portland. The Blazers, Joe Cronin specifically, should have gone to him.

But here we are, where we were always going to be and, frankly, where we should be. Lillard will be 33 in a couple of weeks. He shouldn’t be grooming Scoot Henderson. He should be competing for championships. The Blazers shouldn’t be dangling draft picks to pry Pascal Siakam loose in Toronto. They should be sifting through pick-rich offers that will put the team on a path to contend in the future.

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So where does Portland trade Lillard? Lillard made it clear to the Blazers that he prefers a trade to Miami, a source told Sports Illustrated. The Heat were the Eastern Conference champions last season. They have Jimmy Butler. Bam Adebayo. A win-at-all-cost culture that Lillard will naturally gravitate towards. Free agency was tough on Miami, which saw its starting backcourt of Gabe Vincent and Max Strus sign elsewhere. Acquiring Lillard will more than soften the blow.

Miami, though, may not be able to present the best offer. SI reported earlier this week that the Blazers were lukewarm on Tyler Herro, who will enter the first year of a four-year, $120 million extension next season. Kyle Lowry is a $30 million expiring contract. The Heat have draft picks in ’28 and ’30 they can fork over and sweeten it with swaps in ’27 and ’29.

There will be teams that can top that. Brooklyn, which has Ben Simmons—whose contract (two years, $77 million) is less onerous than it once was—and a whole bunch of appealing Suns picks to dangle. San Antonio—yes, San Antonio—which has cap room, young players and draft capital to deal. Boston, if the Celtics determine a Jaylen Brown super max contract extension is too pricey.

Then there is Philadelphia, which is sorting through options with its own star. The 76ers have engaged several teams on James Harden over the last few days, after Harden opted into the final year of his contract and requested a trade. The Clippers have emerged as the early frontrunner and teams' executives have come away from those discussions with the feeling that the Sixers' motivation was to drive the price up on L.A.

Could Portland horn in on those negotiations? The Clippers want Harden, and L.A. is Harden’s preferred destination. The Sixers would be thrilled to swap Harden for Lillard and pair Lillard with Joel Embiid. Portland could acquire a young player—Tyrese Maxey would be at the top of the list—and collect draft capital from both teams to make it work.

Whatever happens, both the Blazers and Lillard will be better off. Lillard will join a contender. Portland, if it drafts right, can be a contender in the years to come. It was fun to imagine the Blazers pulling off a stunner, of luring Draymond Green to Portland or prying Adebayo away from Miami. But this was always how this was going to end. Lillard’s jersey will hang in the Moda Center rafters one day. Next season, he will wear another.