The Portland Trail Blazers have had an interesting week. They lost to the New Orleans Pelicans in dramatic fashion. Then they bounced back with a semi-gutsy win against the Golden State Warriors, whose
number they appear to have on speed dial. 1-1 may not seem like a definitive record, but when you’re used to losing 75% of your games, that single win can seem like a godsend.
The Warriors game was also Portland’s last before the opening of NBA Trade Season, inaugurated on the day that last summer’s free-agent signings become available to move on the market. 26 games into the season with a 10-16 record, Portland’s status on Trade Day is murky. Are they buyers, looking to shore up an injured roster? Or are they sellers, hoping to bail out of an experiment of bad shooting and mismatched roster members before it gets worse? Opinions are as varied as the number of people asked and none of them conclusive.
Injuries have played a huge part in derailing Portland this year. The Blazers have been without the services of Scoot Henderson and Damian Lillard all season. They’re currently without Jrue Holiday, Matisse Thybulle, and Blake Wesley. It’s not just the bodies absent. Point guards are scarce right now. So is shooting. And Portland is about one sneeze from a big man away from fielding a totally non-functional lineup, as they found out versus the Pelicans.
This complicates matters. Some of these things will get better. But will it be in time to save the season? That remains in doubt. Short-term goals are fine, but you don’t exactly plan a roster around trying to compete for the 10th seed and a fight among also-rans to earn a fingernail-width berth in the playoffs bracket.
In that spirit, there’s one trade–or at least type of trade–that the Blazers should consider regardless of health prognostications. It’s simple and it’s doable. Given how things have unfolded, it also makes sense.
The big “sticks out like a sore thumb” moment of Portland offseason was trading for veteran point guard Jrue Holiday. The former All-Star and All-Defensive wonder is still a fine player. He’s helped the Blazers during the early season, solidifying their defense, organizing offense, and keeping energy high. He’s been everything advertised…a solid candidate for Portland’s non-Deni-Avdija MVP. The Blazers are 6-6 in games Holiday has played, only 3-10 without him.
Even so, Holiday is 35. He’s missed 14 of Portland’s 26 outings. He’s also owed $104 million between now and the time his contract expires in 2028.
Let’s say Holiday returned tomorrow. Let’s also say that enough other players got healthy and Portland returned to their pre-injury form for the rest of the season. If that’s .500 play (which right now seems like a stretch), that would give them 28 more wins. Add that to 10 victories already and you get 38.
What, exactly, are you doing with those 38 wins? Or even 40 or 44, for that matter? Nearing .500 would be great for the Blazers, given where they are right now. But let’s assume Holiday really is all that…the best Holiday imaginable. Why is he being employed at a large salary on a 38-44 win team? Is that the best possible future for him and the franchise?
On top of that are the looming realities of next season: no super-clear avenues of improvement unless the Blazers hop ahead in the NBA lottery, Lillard hopefully returning from injury to play, and Holiday aging another year.
Acquiring Jrue in the first place was a stretch. It was justified by a couple factors. The Blazers gave up Anfernee Simons, who they weren’t re-signing anyway. Portland was trying to make a run at relevance, which Holiday could help with but which also hasn’t panned out so far. (If Portland were soaring right now, we probably wouldn’t be having this discussion. Since they’re not, here we are.)
Reality check: If Holiday were in Simons’ situation, playing on the last year of his contract, we probably wouldn’t be talking about re-signing him in the offseason. Frankly, he’d probably be looking at making a bigger impact with somebody else next year too.
If that’s the case, what’s the justification for Portland to have him back at a cost of $72 million over the next two years? He’s a great player! He always was. He probably always will be. But what’s the fit for this team, in this situation, at his age?
The divide between the Blazers’ timeline and Jrue is not a Holiday thing. It’s a Portland thing. But it exists. And the contract obligation versus the real, tangible effect Holiday will have on Portland’s overall destiny skews towards trading him.
Obviously other teams will have these same concerns, but several will want him. In fact there’s one team in the most desperate of situations that doesn’t need Holiday to be a savior, who might even want only Jrue and exactly Jrue for both on-court and ancillary reasons. More importantly, they might be willing to pay a premium for him.
That team is, of course, the Milwaukee Bucks…the franchise Holiday helped lead to an NBA title in 2021.
Milwaukee is having trouble with superstar Giannis Antetokounmpo. Signing center Myles Turner at the start of the season didn’t help them the way they thought it would. Neither did trading for Lillard two years ago. At this point they are completely out of chips to play: no draft capital until 2031, no significant players to move. They’re dead-ended with a cranky MVP inches away from a trade demand with no hope of pacifying him or replacing him. Keeping Giannis is their only move, but they’re having trouble managing it.
The Bucks can also point to one moment when all of this started to go wrong, when they traded away Holiday to begin with, back in 2023. At this point their best chance of undoing it–making Antetokounmpo and their fans happy–might be getting Jrue back. They already went all-in with the entire stack of chips and they’re about to lose. Holiday is the re-buy that gets them one more hand.
That makes Milwaukee’s 11-16 record less relevant for purposes of this discussion. It also makes Holiday’s contract more palatable to them. They are completely unique in that sense.
And that’s why the Blazers should think about doing one more deal with the Bucks if it’s available.
I do think the Blazers could offer a package of Holiday and, say, Rayan Rupert, depending on cap exceptions. That’s easy from Portland’s perspective.
The return benefit is harder. Kyle Kuzma is the only reasonable contract option to get even close to Holiday’s salary. The Blazers don’t need a mercurial, 30-year-old forward but Kuzma might be marketable as a future trade piece.
The other player who might intrigue is Cole Anthony, a recent add for Milwaukee. He’s 25, a former 15th pick by the Orlando Magic. He’s a slightly-below-average three-point shooter who’s in a big slump beyond the arc this year. But he’s a point guard, athletic, and would probably prosper in Portland’s wide-open style. Turnovers would be the biggest concern. Think of Anthony as an analog for Scoot Henderson, except Anthony has been healthier overall through his career so far.
Neither Anthony nor Kuzma is as good as Holiday. That’s the extra draw for Milwaukee, besides the aura rub. The big question is whether the Bucks might be willing to trade extra draft capital in the future to take their next swing now. If so, that makes the deal more enticing for Portland.
Here’s the real benefit. Per Spotrac (whose trade machine approved this deal by cap rules) the Blazers would shave $8-10 million off of their salary cap this year, depending on who’s included. “Big deal,” you say. They’re over the cap and under the luxury tax either way. True, but Portland is right up against the tax threshold now. Moving beneath it would give them leeway to make further moves without incurring tax penalties.
Even better, Kuzma is scheduled to make $20 million next season. That leaves him as an easy trade candidate if anyone wants him. (Do you think former darling Dejounte Murray is languishing in New Orleans? He’s scheduled to return from injury after New Year’s. Kuzma would get the Blazers near his contract this summer.) But even if the Blazers keep Kouz, $20 million over one year is far different than the $72 million over two seasons owed to Holiday.
Anthony holds an expiring contract and is on a trial run either way. Chances are Scoot Henderson and Cole Anthony would make as interesting of a point guard combo this year as Henderson and Holiday, albeit with fewer wins.
Either way, Jrue’s contract continues to look questionable…and that’s with the youngest, healthiest version of Holiday on the table. The investment isn’t forecast to age well. Getting him was a 2025 move, not a 2028 one. But 2025 is almost gone and 2026 isn’t looking much better.
If the Houston Rockets (or any other team) comes beating down the door for Holiday, that’s a different matter. But if the Bucks are willing to absorb Holiday’s greater salary and perhaps throw in future draft sweetener besides because of their desperate situation, the Blazers might want to look in their direction.
