People still talk about it like it was a normal basketball move. It wasn't. The Jrue Holiday trade Celtics Blazers saga is basically a two-act play that redefined how NBA front offices handle the "second apron" of the luxury tax. Most fans remember the first part: Jrue getting dumped by Milwaukee in the Damian Lillard blockbuster, landing in Portland for about five minutes, and then Brad Stevens swooping in to grab him for the Celtics' 2024 championship run.
But the real story? That's what happened in June 2025.
The Celtics had just won a ring. They were on top of the world. Then, the financial reality of the new Collective Bargaining Agreement (CBA) hit them like a freight train. With Jayson Tatum's massive extension and the team staring down a projected $500 million bill in salaries and taxes, something had to give. When Tatum went down with a torn Achilles in the 2025 Eastern Conference Semifinals, the "win at all costs" math changed instantly.
The Blockbuster Return to Portland
On June 23, 2025, the NBA world stopped. Reports from Shams Charania and others confirmed the unthinkable: the Celtics were trading Jrue Holiday back to the Portland Trail Blazers.
Wait. Back to Portland?
✨ Don't miss: Mexico vs USA Gold Cup Final: Why the Rivalry Never Gets Old
Yeah. The same team that flipped him to Boston in 2023. This time, the deal was built around Anfernee Simons coming to Boston. Initially, there were two second-round picks involved heading to the Celtics, but later reports from The Oregonian suggested those were pulled back, leaving it as a straight-up player swap.
Boston saved about $5 million in raw salary, which sounds like pocket change for a pro sports team. In the world of the second apron, though, that $5 million difference actually saved the Celtics over **$40 million** in tax penalties for the 2025-26 season. It was a cold, hard business decision.
Why the Blazers Actually Wanted Him Back
You’d think a rebuilding team like Portland wouldn't want a 35-year-old guard on a massive contract. But Joe Cronin, the Blazers' GM, saw it differently. Portland was tired of losing. They had a logjam of young guards with Scoot Henderson and Shaedon Sharpe, and Anfernee Simons—while a brilliant scorer—wasn't exactly a defensive stopper.
By bringing Jrue back, the Blazers got:
- A legendary locker room leader for a young core.
- Elite perimeter defense to pair with Toumani Camara and Deni Avdija.
- A culture setter who had just won a title.
Honestly, the results on the court have been weirdly good for Portland. As of early 2026, the Blazers are significantly better when Jrue plays. In games where he’s active, they’ve played roughly .500 ball—a huge step up from the "post-Dame" tanking years. He's currently averaging about 17.4 points and 7.6 assists. Not bad for a "washed" veteran.
The Anfernee Simons Fit in Boston
Boston's side of this has been... rocky.
💡 You might also like: Prince Fielder Body Issue: Why Those Photos Still Spark Conversation a Decade Later
They got younger. They got a guy who can hit 200 threes in a season. But Simons isn't Jrue Holiday. He’s a "flamethrower," as some analysts call him, but his defense has been a struggle in Joe Mazzulla's system. Without Tatum on the floor to draw double teams, Simons has had to work a lot harder for his points.
His scoring has dipped to around 14.3 points per game in Boston. There was even a game against Orlando recently where he only played 18 minutes. It’s a classic case of a player fitting a specific role in one city and looking like a fish out of water in another.
The Financial "Gap Year"
This trade was the first domino in what many call the Celtics' "gap year." Brad Stevens is playing the long game. By moving Holiday's $134 million extension, Boston cleared the books for the future when Tatum returns from his Achilles injury.
It’s a brutal reminder that the NBA is a business. Jrue Holiday was the "missing piece" for a championship in 2024. A year later, he was a salary cap casualty.
Real Impact and Actionable Insights
If you're following the fallout of the Jrue Holiday trade Celtics Blazers deal, here is what actually matters for the rest of the 2026 season:
- Watch the Blazers' Defense: They ranked near the top of the league in points allowed after the All-Star break last year. If Jrue stays healthy, they might actually sneak into the play-in tournament.
- Monitor Simons’ Contract: He’s on an expiring deal. If he doesn't start clicking with Jaylen Brown soon, expect Boston to flip him again before the deadline for more draft capital or a defensive wing.
- The Second Apron is Real: Every contender is watching Boston. If the Celtics can successfully "reset" their finances without falling into the basement of the standings, other teams like the Suns or Bucks might follow the same blueprint.
The trade wasn't just about basketball talent. It was about survival in a league where the rules are designed to break up great teams. Portland got their mentor; Boston got their tax relief. Whether it leads to another banner in Boston or just a few more wins in Portland remains to be seen.
🔗 Read more: MN Vikings QB Depth Chart Explained: Why the Room is Suddenly Wide Open
To stay ahead of how this affects your fantasy roster or betting lines, keep a close eye on Jrue's "minutes played" totals in Portland. The Blazers are protective of his 35-year-old legs, and his absence usually leads to a defensive collapse for the young squad. For the Celtics, watch the plus-minus stats for Simons when he shares the floor with Derrick White—that’s the backcourt pairing that will decide if Boston remains a playoff threat this year.