Jrue Holiday Breaks Silence: No Hard Feelings Toward Celtics or Brad Stevens After Blockbuster Trade to Portland

 A Classy Exit from a Championship Core

On December 30, 2025, Jrue Holiday finally spoke publicly for the first time since the stunning offseason trade that sent him from the defending champion Boston Celtics to the Portland Trail Blazers. In a wide-ranging interview with The Players’ Tribune that dropped just 48 hours before the Celtics faced the Blazers on New Year’s Eve, Holiday made his stance crystal clear: he harbors zero resentment toward the organization, Brad Stevens, Joe Mazzulla, or his former teammates.

“Boston gave me the greatest year of my professional life,” Holiday wrote. “Banner 18. Parade down Boylston. Playing with some of the best teammates I’ll ever have. I’ll never have anything but love for the city, the fans, and especially Brad. What he did for me and my family goes way beyond basketball.”

The trade, which sent Holiday and Kristaps Porziņģis to Portland in exchange for Anfernee Simons, a massive haul of future draft picks, and salary relief as Boston reset beneath the second apron, shocked the NBA world when it was finalized in late June 2025. Many assumed Holiday would feel betrayed after being moved less than 12 months after signing a four-year extension and playing a pivotal role in the 2025 title run. Instead, the 35-year-old two-time All-Star has handled the departure with the same grace and professionalism that defined his two seasons in green.

The Trade That Changed Everything

To understand why Holiday’s words carry so much weight, context matters.

Boston entered the 2025 offseason facing an impossible financial situation: the highest payroll in league history, both Jayson Tatum and Jaylen Brown on supermax deals, Derrick White extension-eligible, and the new CBA’s second apron restrictions threatening to freeze the team’s ability to aggregate salaries or sign players for years. Ownership made it clear they were unwilling to pay repeater tax penalties that could approach $500 million over the next four seasons.

Brad Stevens, in one of the most painful decisions of his executive career, chose to break up the championship core rather than let it slowly suffocate under luxury-tax constraints. Kristaps Porziņģis, coming off an injury-plagued playoff run, was the first domino. Holiday, who had just turned down more money elsewhere to stay in Boston the previous summer, became the second.

Portland, armed with cap space and a desire to accelerate their rebuild around Scoot Henderson and Shaedon Sharpe, offered Anfernee Simons (a 26-year-old scoring guard on a team-friendly deal) and multiple first-round picks. Stevens took the deal, knowing it was the only way to create long-term flexibility while staying competitive in the short term.

Holiday’s Emotional Goodbye That Never Felt Bitter

Those close to the situation say Holiday never once complained privately. When informed of the trade, his first question was reportedly about how it affected the Celtics’ chances of repeating. His second was whether Boston would be taking care of the training staff and security personnel who had become family to him.

He spent the days after the trade calling former teammates individually: Tatum, Brown, White, Hauser, Pritchard, even rookies like Hugo Gonzalez. He FaceTimed the equipment staff. He sent a long text to ownership group members thanking them for “the greatest professional chapter of my life.”

“People keep asking if I’m mad,” Holiday told The Players’ Tribune. “Mad at what? Brad was honest with me from day one. He told me the financial realities. He told me ownership didn’t want to go into the repeater forever. He asked what I wanted, and I told him I wanted whatever was best for the franchise long-term. He made the move that keeps Boston competitive for the next decade. How could I be upset with that?”

Life in Portland: A Surprising Fit

Contrary to early narratives that Holiday would be miserable on a young, rebuilding Blazers team, the two-time champion has quietly become the exact veteran presence Portland desperately needed.

Through December 31, 2025, the Blazers sit at a surprising 18-15, tied for the 7th seed in the West. Holiday is averaging 14.8 points, 6.8 assists, 4.2 rebounds, and 1.6 steals while shooting a career-high 42% from three. More importantly, his on/off numbers are elite: Portland is +11.4 per 100 possessions with him on the floor.

Scoot Henderson credits Holiday for his December breakout, repeatedly calling him “the best mentor I’ve ever had.” Shaedon Sharpe says Jrue texts him film clips at 2 a.m. after bad games. Even Anfernee Simons, who was traded for Holiday and initially felt the pressure of replacing a champion, now says playing alongside Jrue has “made me understand what winning really looks like.”

Off the court, Holiday and his wife Lauren have fully embraced Portland. They’ve already hosted multiple team dinners, started working with local youth organizations, and Jrue has been spotted at multiple Oregon high school games scouting for his AAU program.

The Brad Stevens Friendship That Never Wavered

Perhaps the most revealing part of Holiday’s essay was his defense of Brad Stevens, who has faced criticism from some corners of Celtics Twitter for “breaking up a championship team.”

“Brad is the most honest person I’ve ever dealt with in this league,” Holiday wrote. “He doesn’t play games. He doesn’t lie to save feelings. When he called me into his office in June, he laid out every scenario. Stay and potentially lose the ability to improve the team for years. Or make a move that hurts now but keeps Boston in contention for the next ten years. He cried. I cried. Then we hugged it out and got to work figuring out where I could still compete at the highest level.”

Holiday revealed that Stevens gave him veto power on any trade destination. When Portland emerged as the frontrunner, Stevens called Holiday personally to walk through how the Blazers’ young core reminded him of the 2017-18 Celtics team that made the Eastern Conference Finals without Kyrie and Hayward.

“Brad basically sold me on Portland harder than Chauncey Billups did,” Holiday laughed.

The Celtics Perspective: Pain That Turned Into Gratitude

In Boston, the trade has worked better than anyone dared hope. Anternee Simons has been electric next to Jaylen Brown, Payton Pritchard earned a starting job, and the influx of future picks gives Stevens flexibility for the post-Tatum/Brown era whenever that comes.

But no one pretends it didn’t hurt. Jaylen Brown still calls Holiday “my brother” in every interview. Tatum FaceTimes him before every big game. Joe Mazzulla openly says the locker room has never been the same without Jrue’s presence.

When asked about the upcoming December 31 matchup, Holiday’s response was pure class:

“I’m gonna try to kick their ass for 48 minutes. Then I’m gonna hug every single one of them afterward. That’s how we do it in this family.”

A Legacy of Class in a Cutthroat Business

In an era where superstar trade demands and public subtweets dominate headlines, Jrue Holiday’s handling of his departure from Boston stands out as a masterclass in professionalism.

He never demanded a trade. Never leaked stories to pressure the front office. Never took shots at ownership for not paying the tax. Instead, he thanked them for the opportunity, understood the business decision, and went to Portland determined to help another franchise build something special.

As he wrote in closing:

“I won a championship in Boston. I’ll never need another validation in this league. Banner 18 hangs forever. But watching Jaylen go for 50, watching those young guys in Portland grow, watching Brad build another contender… man, I’m just grateful to be part of this game. The relationships are what last. The rings are nice. But the love? That’s forever.”

When the Celtics and Blazers tip off on New Year’s Eve 2025, there will be no villain in Jrue Holiday. Just a champion who understood that sometimes the hardest decisions are the most necessary ones, and chose gratitude over bitterness every step of the way.

Brad Stevens summed it up best in his own statement after Holiday’s essay dropped:

“Jrue Holiday is the best teammate I’ve ever been around. Not just because of what he did on the court for us, but because of who he is as a man. We’re better because we had him for two years. And I’ll spend the rest of my life trying to repay what he gave this organization.”

In the end, that’s the ultimate respect. Not the trade exception or the picks or the cap space.

Just two men who love basketball, who made an impossibly hard decision together, and somehow came out even closer on the other side.