Following a two-season stint with the Boston Celtics, Jrue Holiday was traded to the Portland Trail Blazers for Anfernee Simons in May 2025. Though the Celtics’ plans to rework their roster were obvious, Holiday’s trade wasn’t without rumors.
The Trail Blazers, on their end, have their priorities sorted for now — especially with Damian Lillard back on the team. However, despite their recent move, it might not have been a smooth-sailing trade for Holiday.

Jrue Holiday Speaks Up After Rumors Hint at Issues With Portland Trade
In June, an NBA insider reported that Holiday was “pi**ed” at being traded to Portland.
The Celtics, who couldn’t repeat their title win in 2025, were looking to trade players to free up space. This included players like Kristaps Porziņģis and Holiday, who had developed their own connections in Boston.
Holiday, specifically, was a prime candidate for a trade. A reliable playmaker and defender with valuable experience, he had three years left on a four-year, $134 million contract. After he was traded to the Blazers, some even considered a second trade for the veteran point guard.
However, in a recent interview with RG, Holiday highlighted what’s important about his trade to Portland.
“Goal is to win,” Holiday told RG. “The goal is to win and to make some noise. I think that after the last few years of what has happened after Damian Lillard being traded — and then now Dame’s back — I think it’s an exciting time here in Portland. It’s an exciting time to be a Trail Blazer, and I’m excited to be part of it.”
Holiday also took a chance to praise the Trail Blazers’ roster. He noted that he wanted to highlight the team’s talent, singling out Scoot Henderson and Shaedon Sharpe and their “smart” ways of playing the game. Hyping them further, Holiday said:
“They’re going to be so good, and I feel like all they need is time. I feel like the time is now, because they have all the tools. I’m super excited to play with them.”
Of course, nothing might be as good as Holiday teaming up with Lillard. The 35-year-old revealed that they have known each other for a long time. In fact, Lillard even texted Holiday after their trades, saying: “Man, we really got a chance to be good.”
Holiday, a consistent presence in the league, averaged 11.1 points, 4.3 rebounds, and 3.9 assists while shooting 44.3% from the field.
Before joining the Trail Blazers and Celtics, Holiday also played for the Milwaukee Bucks (2020-23), the New Orleans Pelicans (2013-20), and the Philadelphia 76ers (2009-13).
