Lowe: Why the Damian Lillard-Blazers breakup actually began eight years ago

Zach Lowe (@ZachLowe_NBA) is a senior writer for ESPN Digital and Print.

NO TEAM ARRIVES at the crossroads the Portland Trail Blazers face now because of a single recent decision — in this case Portland using the No. 3 pick on Scoot Henderson instead of trading the pick to appease Damian Lillard.

The Blazers’ front office was sincere in its belief it could straddle two paths — take Henderson, and work trades and free agency to build a competitive team around Lillard. It would be hard, and require luck. For Lillard, the odds of success were too long. That was a fair conclusion, too.

I have not heard convincing evidence that a sensible deal exchanging the No. 3 pick (and another player, likely Anfernee Simons) ever materialized for Portland. Moving up in the lottery — jumping from No. 5 to No. 3 — changed everything. For most talent evaluators, Henderson is better than the typical No. 3 pick — maybe much better.

Trading a prospect that valuable for a veteran is a weighty decision. It has to be the right veteran — available, reliable, good enough to put you into the inner circle of title contention, hopefully not so old you have completely knee-capped your future.

The Brooklyn Nets never showed interest in swapping Mikal Bridges for that Simons/No. 3 package, sources said; it’s unclear if the teams discussed it. The Miami Heat chuckled at Portland potentially asking about Bam Adebayo.

The LA Clippers would push back on the notion that they genuinely explored Paul George’s trade value, but if they had, you cannot flip Henderson for a 33-year-old who hasn’t played in more than 56 games since 2018-19 — let alone one eligible for a massive extension.

The New Orleans Pelicans and Toronto Raptors weren’t ready on draft day to pivot away from Zion Williamson, Pascal Siakam, or O.G. Anunoby, sources have said. Williamson is a franchise-changer when healthy, but he’s rarely healthy. Siakam and Anunoby are very good — Siakam is an All-Star — but would either have vaulted Portland into the ring of championship favorites?

In a strange way, you can trace the seeds of Lillard’s departure all the way back to an opportunistic trade from eight years ago: the Blazers acquisition at the Feb. 2015 trade deadline of Arron Afflalo from the Denver Nuggets in exchange for Will Barton and a lottery-protected 2016 first-round pick. It was a sound move made with an eye on both the present and the future — but almost nothing after that day unfolded quite as planned.

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