Jrue Holiday has been central to the modest success the Portland Trail Blazers have enjoyed this season. On top of starring in more than his fair share of games, he’s served as this team’s on-court sage, imparting experience from 17 years, two NBA championships and a laundry list of individual accolades.
The Blazers will make their return to postseason play this week, competing in the Western Conference Play-In tournament, a feat that would not have occurred without Holiday — I’m convinced of that.
After this season, Holiday has two years, including a player option, remaining with $72 million owed. With his 36th birthday fast approaching, the deal could very well be his last non-veteran minimum contract.
The size and length of Holiday’s deal was one of the concerns that followed him on his arrival in Portland last June. The Blazers sent guard Anfernee Simons and his expiring contract to the Boston Celtics for Holiday. Simons’ unrestricted free agency would have helped clear the Blazers’ books this summer.
No one was doubting Holiday’s pedigree.
But before this season, there had been a noticeable downturn in production during his two years in Boston where he served as a relatively smaller cog in a much larger championship wheel. His New England years were his least productive relative to his time spent with the Philadelphia 76ers, New Orleans Pelicans, and Milwaukee Bucks. Those two campaigns delivered 11.8 points on 39.2 percent from three, 4.9 boards, 4.4 assists and 1.0 steals on 16.1 percent usage.
But Holiday has proven his critics wrong this season, returning to a larger role, averaging 16.2 points on 38.1 percent from three, 4.6 boards, 6.1 assists and 1.1 steals on 23.5 percent usage in Portland.
As a Blazer, he’s re-affirmed his status as one of the best two-way players in the league, an ability that helped quell Kawhi Leonard last night Despite Holiday giving up a couple of inches. More than that, he’s been a veteran presence for a young Blazers outfit, looking for more wins than it had registered in each of the past four seasons.
The former UCLA product is a professional, someone who knows what it takes to reach the highest heights. This was highlighted by the Blazers honoring Holiday with the 2025-26 Maurice Lucas Award, a prize given to the Blazer who excels not only on the court but also off.
Blazers Guard Rotation
General Manager Joe Cronin will have a number of decisions to make this summer. Not just on whether to bring back Robert Williams III and Matisse Thybulle but also which contracted players need to be shipped off in trades. Given owner Tom Dundon’s recent words, Cronin may have more freedom to be aggressive in trades.
The 6’4 Holiday is a chameleon. Boasting a 6’7 wingspan, he has the size of a guard, the strength of a forward, and skills that can work across all five positions. Though some consider him a point guard, Holiday can be just as effective off-ball.
This versatility allows him to play alongside pretty much anyone, including one of Damian Lillard or Scoot Henderson, but not both.
I’ve written about Henderson ad nauseam. The former G League Ignite standout should enjoy a long career. Whether he’s a starter or not remains to be seen. But the 22-year-old showed this season, that he can serve next to Holiday when required.
If Lillard, returns to form next year, then he and Holiday would prove to be a formidable backcourt, albeit one sharing a collective age of 72. After years watching them line up against each other, it’d be a sight to see them play together even if they are relative basketball geriatrics.
But if they do share the court, how long can they do it? The one thing this Blazers team has going for is youth and speed. I’m not sure they can get away with an aging backcourt tandem struggling to keep pace with their more youthful brethren.
Trading Holiday
Given Holiday’s return to form this season, he’s surely going to be one of Portland’s best trade assets this summer, regardless of his age.
Despite Holiday’s already-discussed resurgence, Cronin has to be thinking about the longevity of this team. It’s unlikely, though not impossible, the Blazers are winning a title next season. Consequently, he also needs to be looking forward, potentially to where this squad going to look like in 2028 and 2029, when both Lillard and Holiday are preparing for their 40th birthdays.
Good teams need good veterans. But too many is a problem when they’re earning big bucks and are key parts of the rotation.
Perhaps, if Lillard hadn’t returned, holding onto Holiday long-term makes sense. But of the two of them, Holiday is surely the odd man out. Lillard’s connection to the city combined with his no trade clause solidify his place in Oregon.
As of right now, there may not be a better time to move Holiday. He’s helped lead the Blazers back to relevance. He might help deliver the Blazers a difference-maker.
The issue is, that difference-maker has to be available. I’m not sacrificing a player of Holiday’s ilk just for the sake of trading him. Unlike Jerami Grant, who’s value could be lower, the Blazers are going to need a player of consequence in return if they trade Jrue.
Conclusion
Five things matter here.
One. I really, really, really want to see how a Lillard-Holiday backcourt looks, even if they are in their mid-30s.
Two. The Blazers will need to move Holiday at some point.
Three. Trading Holiday doesn’t ensure that Lillard and Henderson can share the court together.
Four. Holiday may never bring back more in a trade than he does right now.
Five. The Blazers can’t afford to trade Holiday for cents on the dollar.
Ultimately, the Blazers will need to move Holiday. But they should only do so when the right deal materializes. Unless the Blazers are getting the optimum return, Holiday is better off with this team than with anyone else.
What do you think? After the decent stats, the accolades, and a few wins to his name, do you consider Jrue Holiday too valuable to the Blazers to move or would you be on board with Jrue as possible trade leverage for Portland to make the next step? Share your thoughts in the comments below.
