The Portland Trail Blazers are already entering 2026-27 shorthanded with shooting guard Shaedon Sharpe suffering a torn meniscus. Portland's high flyer will be reevaluated in six months, likely sidelining him until at least the All-Star Break.
One silver lining to the brutal injury is that it somewhat clears up the Blazers' self-created backcourt mess. It's suddenly much more realistic to carve out enough minutes for Damian Lillard, Ja Morant, Scoot Henderson, and Jrue Holiday as the key pieces to the backcourt picture.
But what if the Blazers also considered trading veteran Holiday to clear up even more room?
Blazers should sell high on Jrue Holiday to fix backcourt logjajm
Can you imagine the growth and minutes Henderson would give filling in for Lillard and Morant? He's gotten much better off-ball, making it a realistic fit thanks to a growing 3-and-D game.
What also gets lost in Portland's backcourt discussions is that it's still Deni Avdija's offense. His evolving point-forward game was a huge reason the Blazers made the postseason last year.
Even if the Blazers were to trade Holiday, they'd have an established offensive hierarchy with Avdija as a point forward and Morant/Lillard as the secondary playmakers. They'd be worse in the short term, as every team is inevitably better wherever Holiday goes. But that's also precisely why now would be a good time to move on from Holiday, receiving significant assets if a contender believes he's the missing piece to get them over the top as he was in those championship stints with the Milwaukee Bucks and Boston Celtics.
He may have contributed to Portland's playoff push with a resurgent season, but unfortunately, Holiday isn't going to be getting a ring from his stop with the Blazers anytime soon. We saw that admission through the Blazers' conservative offseason trades, where even headliner star Ja Morant was acquired for a negative asset in Jerami Grant, Kris Murray, and zero draft picks.
Taking a step back in the short term by flipping Holiday for future assets is worth considering. It would not only get them young assets that better fit their young core's timeline, but it would also free up a tremendous amount of financial space in order to retain said core. Holiday would be an ideal piece to move from a financial standpoint for Portland so that they could get the flexibility to renegotiate and extend Avdija.
They already won the Holiday deal but should likely consider cashing in their chips while they still have a 36-year-old, $35 million somewhat injury-prone player still with value around the league.
It's a difficult but necessary direction they should take to gain more clarity with their younger backcourt pieces. Sharpe's injury may have saved the Blazers from themselves by solving at least one side of the equation.
While they don't appear to be actively pursuing trades for Holiday, it makes sense for that to be the next domino to fall, giving Portland an actual backcourt to work with going forward and picking up assets to improve their future outlook along the way.
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