Jrue Holiday's Struggles Spotlight Blazers' Dilemma Ahead of Trade Deadline
The Portland Trail Blazers’ blowout loss to the New York Knicks wasn’t just another tough night on the road - it doubled as a spotlight game for Jrue Holiday, a veteran guard who’s drawing interest from the Knicks as the Feb. 5 trade deadline approaches. But if Wednesday night was meant to be a showcase, it didn’t exactly go according to plan.
Holiday finished with just five points for the second straight game, continuing a cold stretch since returning from injury. In 22 minutes, he added four assists, two rebounds, and four turnovers, shooting just 2-of-7 from the field. The Blazers, meanwhile, were overwhelmed in a 127-97 loss that never felt close.
Now, Portland finds itself in a tricky position - not just because of Holiday’s recent play, but because of what his future means for the franchise.
A Contract That’s Getting Harder to Ignore
Let’s be clear: Jrue Holiday is still on a minutes restriction, and it’s fair to give him some grace as he works his way back. He’s a proven two-way player with championship pedigree - the kind of guy who’s been the final puzzle piece for contending teams in Milwaukee and Boston.
But in Portland, the context is different. The Blazers are rebuilding, and Holiday’s age, injury history, and contract loom large over that process.
Holiday hasn’t played 70 games in a season since 2017-18, and at 35, the wear and tear is showing. The quickness that once separated him from other guards isn’t quite the same. And when you pair that with a hefty contract that stretches through 2027-28 - including a $37.2 million player option in his age-37 season - it’s not hard to see why Portland might be getting nervous.
If this version of Holiday is your highest-paid player, it raises serious questions about roster flexibility and long-term planning. Especially when you’ve got young pieces like Deni Avdija outperforming their current deals and deserving more investment.
The Clock Is Ticking
When the Blazers acquired Holiday, the plan was to keep him - not flip him again. But plans change, especially when the on-court product doesn’t match the financial reality. With the trade deadline just days away, Portland has to consider its options.
Does Holiday still have value around the league? Absolutely.
His playoff experience and defensive prowess are still coveted traits, especially for teams with championship aspirations. But there’s no guarantee that front offices will be eager to take on his contract, particularly under the league’s new CBA, which makes bloated deals even harder to navigate.
Still, Portland owes it to itself to explore the market. Holiday may no longer be the ideal fit for a team looking to build around a young core and grow into a contender. His skill set is still valuable - just not as much to a team in Portland’s current position.
A Proven Winner - In the Right Situation
Holiday’s résumé speaks for itself. He was a key piece in Milwaukee’s 2021 title run and brought veteran leadership to Boston during their deep playoff pushes.
But for Portland, the stakes are different. This isn’t a team on the brink of a Finals appearance - it’s a group trying to claw its way back into postseason relevance.
Keeping Holiday around might feel like a stabilizing move, but it could also be an anchor that slows down the rebuild. His value is likely to decline from here, and the longer Portland waits, the harder it could be to move him.
Whether it’s the Knicks or another team, the Blazers need to find out if there’s a contender out there willing to bet on Holiday’s experience - and absorb his contract in the process. Because for a team like Portland, holding onto him might cost more than just cap space. It could cost them momentum in a rebuild that’s already tough enough in today’s NBA landscape.