Jrue Holidays on Celtics-Trail Blazers trade, Brad Stevens’ honesty and enjoying Portland

PORTLAND, Ore. – Jrue Holiday has no hard feelings toward the Boston Celtics after they traded him over the offseason. In fact, he said Sunday he was grateful for the way Brad Stevens handled the situation.

Holiday said Stevens alerted him early in the offseason that a trade could potentially be in the works. In June, that possibility came to fruition when the Celtics agreed to send Holiday to the Portland Trail Blazers for Anfernee Simons.

“Brad communicated that (a trade was possible), and I appreciate him for it – that it was a possibility,” Holiday said. “He even said that it might not happen; we don’t know. So, just the fact that … I mean, Brad being Brad, but him having hard conversations and being able to say something like that, I respect him. I’m really glad that he was able to just give me fair warning.”

Stevens has said the Celtics’ salary-cap situation dictated how they approached the offseason. In addition to Holiday, the team also traded Kristaps Porziņģis in a quest to get under the NBA’s second apron. Though the Celtics tried to keep Al Horford and Luke Kornet, who were both free agents, the desire to stay under the second apron limited what they could offer the two big men. Horford signed with the Golden State Warriors and Kornet chose to join the San Antonio Spurs. That left Boston without four key figures from its 2024 championship run.

Though Holiday did not anticipate where everyone would end up, he said he recognized that the Celtics would likely need to make significant roster changes after losing to the New York Knicks in the second round.

“I think we know basketball a little bit in terms of how the money is and how not everybody can stay,” Holiday said. “So, we knew that there was going to be a change. You just don’t know what the change might be. I don’t think that I speculated or I saw what was going to happen, where everybody was going to go. No. But I think when you look at it in terms of like the business side of it, yeah, you kind of know that some change is going to happen.”

Given the reality of the Celtics’ financial situation, the conversation with Stevens didn’t catch Holiday completely off guard.

“I think you’re never really surprised by anything much anymore,” Holiday said. “You know what I mean? So, I wouldn’t say I was surprised, but also just it’s a part of it. It’s a part of this life.”

Maybe it wasn’t surprising, but the end came quickly for the team’s championship core. One week, the Celtics were one of the title favorites. The next week, they were out of the playoffs and staring at a long absence for Jayson Tatum after he tore his Achilles during the second round. By the end of the offseason, they had lost five regular rotation pieces, including Tatum.

“It’s not my first setting,” Holiday said. “So, I think I just look at it like it’s a part of the game. It’s a part of this lifestyle where you have to be able to adjust as quickly as possible. Not only me, but I mean, Boston had to too, not only as a team, but like as a city where, we went from favorites to everything just kind of everywhere – a lot of people going different places. So, I look at it as an opportunity and everything I guess you kind of have to look at it like that – is what do you do with your opportunity?”

The Blazers had previously acquired Holiday in 2023. Because they weren’t contenders at the time, though, he informed the organization he would like to be traded again to a team with a better chance to win. Portland respected his wishes and dealt him to the Celtics.

The second time around, the Trail Blazers acquired Holiday to keep him. After discussions with their coach at the time, Chauncey Billups, and some of the players on the team, Holiday said he quickly grew excited about his new location.

“I was surprised because I didn’t think it was an option,” Holiday said. “I think that the times that I had heard of something or rumors, it was always somewhere else. But again, them circling back to come get me, meaning they wanted me, and I loved that.”

“It was exciting for something new,” added Holiday “It was exciting, especially me at my ripe old age, to be able to come into a situation where I could teach a little more and be a lot more of an example. And then, we had some injuries early, Scoot (Henderson) was out early, and I got to play a lot. So, that was also really fun.”

Yeahhh, Jrue 😤 pic.twitter.com/v5YZxkUzre

— Portland Trail Blazers (@trailblazers) November 13, 2025

Holiday, who has missed most of the season with a calf injury, has played in only 12 games for the Trail Blazers. When in the lineup, he has been extremely productive while averaging 16.7 points, 8.3 assists and 5.3 rebounds per game. Because of all the talent surrounding him in Boston last season, he rarely had the chance to handle the type of role Portland has asked him to play.

“I think sacrifice is … I don’t know if you want to call it levels, but you always have to sacrifice something,” Holiday said. “And I think the willingness to do it is what makes everybody a little better. Maybe showing by example makes everybody else kind of sacrifice a little bit. So, I think I’ve just maybe been that type of player, but me kind of getting back to being more of a prominent role has been pretty nice.”

Other than his injury, Holiday said he has appreciated his time in Portland so far.

“It’s been great besides not playing,” Holiday said. “A lot of guys have been injured, and you hate to see that, but other than that, me adjusting here has been pretty seamless. The team is great. Staff is great. I’ve been enjoying myself.”