The Portland Trail Blazers were initially criticized in their one-for-one swap of Anfernee Simons for Jrue Holiday with the Boston Celtics. Many expected Portland to move on from Simons to get ahead of his expiring contract, but the expectation was that they'd turn Simons into future assets. Blazers GM Joe Cronin had other plans, acquiring an expensive, aging, and somewhat injury-prone star in Holiday.
Well, one season later, you can officially add Holiday to the list of bold trades Cronin was initially criticized for that look like no-brainers in retrospect.
It's not quite on the same level as stealing Deni Avdija from the Washington Wizards, especially since the Celtics' motivation for moving Holiday was largely financial. But it is surprising that Simons is all the Celtics were able to get for a two-time NBA champion, especially after seeing Simons flipped for Nikola Vucevic -- a piece head coach Joe Mazzulla couldn't even rely on in the playoffs -- at the February deadline.
Blazers stole Jrue Holiday from the Celtics
The declining value of Simons and Holiday's resurgent season proves the Blazers did a great job of maximizing value last summer. That puts Portland's front office in an ideal position entering this offseason, where they can take the roster in a variety of directions under new owner Tom Dundon.
Holiday is expected to receive trade interest around the league, and the Blazers could cash in their chips for those future assets they were criticized for never receiving for Simons. Or, Portland could take the roster in the other direction, pursuing a star like Giannis Antetokounmpo, Jaylen Brown, or someone else entirely.
Holiday has proven to raise the ceiling of contenders with rings to show for it in Milwaukee and Boston. Ideally, Portland would be the next in line. With the Giannis sweepstakes in particular, Holiday would also be a key piece in attempting to keep the Greek Freak in Portland long-term.
The Blaers wouldn't have this amount of flexibility had they kept Simons. In fact, they'd be stuck in a lose-lose scenario, either let him walk in free agency for nothing, or overpay for a player archetype that's rapidly losing value around the league. Portland is in a much better position with Holiday, regardless of where they decide to go from here.
Perhaps the best part of having an unselfish, versatile star in Holiday is that they don't even need to force a decision. The Blazers acquired Holiday with the intention of keeping him this time around. At his exit interview, Holiday expressed a mutual feeling, stating his desire to stay and build something special in Portland.
The Blazers should be open to listening to offers to see if anything blows them away. But keeping Holiday around has its short and long-term benefits. He's proven to be a seamless fit with any roster and system throughout his career, and it's been more of the same in Portland.
One season later, it's safe to say Portland's polarizing decision to trade for Holiday never even should've been polarizing in the first place. It's not a coincidence they returned to the playoffs for the first time in five years, the first season they have Holiday.
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