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Grant Hill: 'Contrary to popular belief, I do like Jaylen Brown. I love his game, and things got difficult there with that team. In putting the team together, just to give some context, we had Kawhi Leonard on that penciled in on that team, and he got hurt at the end of that season in 2024. He came to camp, he wasn't right, and so we had to pivot. A couple of things happened at that camp, and people want to believe what they want to believe, but at the end of the day, Kevin Durant showed up, he was hurt. He had a grade one calf strain, and I think we all have PTSD from the last time he had a calf strain, so we were very patient with him. Jayson Tatum had just had a baby, so he showed up late. Joel Embiid was, you know, we knew we were managing him, but we needed him for Nikola Jokic against Serbia, because that was the matchup. We didn't have our full roster, and then we started looking around and saying, oh man, like Jrue Holiday was so important for us in the FIBA game. A point guard who can play his role, ball pressure, the whole nine. If Jrue got hurt, our point guards were Jrue Holiday and Stephen Curry, and defense wasn't necessarily their strong point. It was like, okay, let's bring in insurance for Jrue Holiday and like Derrick White. So that was the thought process.'
That leads to the unspoken part of this trade: more deals are on the way. Have to be. The Blazers now have four point guards — Morant, Lillard, Jrue Holiday and Henderson — so unloading one or two seems likely. If I was to guess, I would imagine Holiday, because of his contract and because of his skill set, is the more likely candidate to be traded next.
The Blazers are still in the market to make another deal. They want more big-man depth and realize they have a logjam of four point guards with Morant, Lillard, Jrue Holiday and Scoot Henderson, but the team does not feel it is essential to unload one of its guards. The Blazers believe the four guards can co-exist, in large part because the team believes Holiday can alleviate the redundancy by playing him off the ball as a shooting guard or small forward.
The Ja Morant trade caught many around the NBA by surprise, as the oft-injured Memphis Grizzlies guard was traded to the Portland Trail Blazers for Jerami Grant and Kris Murray. One executive from another team I talked to called the deal “confusing," citing the Blazers' glut of guards with Damian Lillard returning from Achilles surgery and Jrue Holiday and Scoot Henderson under contract. He wondered whether there was a corresponding deal the Blazers were working on to clear up the position.
As he evaluated who would represent him, Jrue Holiday could have prioritized a sports agency that conducted an elaborate sales pitch. One that promised a lucrative contract regardless of whether Holiday matched his All-Star potential. One that promised hefty endorsements regardless of his marketability. Instead, Jason Glushon convinced Holiday to join his new independent sports agency in 2016 by avoiding any self-promotion or salesmanship. “He was completely upfront and honest with me,” said Holiday, who currently plays with the Portland Trail Blazers. “He’s never ‘BSed me, not once. I think especially when you get in a field that I’m in, you can tell when people are trying to ‘BS you or when they’re being completely honest. From the beginning, he’s always done that.”
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Glushon conceded he lacks a “perfect answer” to explain how his independent sports agency has thrived in a competitive landscape. Glushon credited a former mentor (former longtime agent and current Detroit Pistons vice chairman Arn Tellem). He had extensive experience at Wasserman as an intern (2006-2009) and as an agent (2009-16). He praised his company’s head of sales and marketing (David Braun) and agent (Ryan Leff) for ensuring enough bandwidth to support their clients and families. But Holiday and Robinson validated Glushon’s belief that candor and substance have also become increasingly valuable amid a fluid industry. “It’s about being honest and fighting for our players and their families,” Glushon said. “You can’t promise hundreds of millions of dollars. You can’t promise they’ll get traded to the right team. But you can promise preparation and being proactive to do your best. We have had some good partnerships and good successes.”
The second was the inclusion of Holiday in the trade that brought superstar Lillard from Portland. "Looking back on it, the one thing we did that changed everything was put Jrue in that trade," a Bucks source said. "Jrue was such a leader on and off the floor. He would do things like if Giannis was holding the ball too much, Jrue would just bring it up and play with everybody else without making it a thing. He was a pro at it. "But Jrue was in the deal [for Lillard] because we thought we needed offense over defense. But once he was gone, we lost our whole defensive identity. It's not so much that getting Dame was a mistake. He would've been perfect if we still had Jrue."
After the Trail Blazers were eliminated from the playoffs by San Antonio, guard Jrue Holiday made it clear he wants to back in Portland again for 2026/27, according to Joe Freeman of The Oregonian. “I hope so. I don’t like being traded and moved and stuff,” Holiday said. “I like being a part of something and building with the team and seeing the progress and going through the progress with them. So I hope so. I’d love to be here. “Honestly, just kind of how we ended the season, fighting and clawing, knowing that we have a team that has proven ourselves to some extent to be a playoff team. We have a good mix of older gentlemen and then young guys that are still hungry. You hear them. They’re still in the gym now and it’s been two days (since) we lost in the playoffs. So I’m really excited for that.”
Anonymous NBA scout on Holiday’s future in Portland: “You’re locked in. That’s a lot of money. I don’t think he’s valued at that number anymore. And you’ve got two more years of it. Obviously he got overpaid because (Boston) won the championship and he was valued high. But it’s not like he performed like a $35 million player. I like him. I just think, ‘How are you going to use him moving forward? Dame (Lillard) is coming back and you have Scoot.’ I will say, Jrue’s best value right now, if I was in the organization, is trying to teach Scoot the point guard position. To me, in addition to what he does on the court, Jrue should be a mentor to Scoot. He’s a true professional. He works his butt off. He handles himself on and off the court. He’s someone every young player should look up to. He’s also a very good, two-way player. If Scoot can take any knowledge from anyone, that’s the guy I would take the knowledge from. Jrue, just being a leader and being who he is, I think that will help offset his age and that contract. If he can add that piece of it and be a mentor to Scoot, that’s a big positive.”
Anonymous NBA scout on Holiday’s season: “Jrue is just the ultimate glue guy, a true professional on both sides of the floor. When they traded for him, it was like, “Why are they doing this? Let him go somewhere he can compete for a championship.” But Jrue is going to play hard every night, do what’s needed to be done to win games, whether that’s play on the ball, off the ball, whatever. And he was good for them. I love Jrue and the way he complements Toumani (Camara) defensively. That’s two good perimeter defenders.”
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Word is that Portland fully expects Lillard to return next season from the Achilles tear he sustained in April 2025 to potentially join Jrue Holiday in its starting backcourt... With Henderson in the mix as well. How all the pieces fit together remains to be seen, but it's likewise expected that the Blazers will field plenty of external trade interest in Holiday in coming weeks and months.
Sean Highkin: Jrue Holiday on Scoot Henderson: "I think when Scoot got comfortable, you saw what he's capable of and that's the tip of the iceberg. Him getting a full season of being healthy ... I think he has a bright future."
