BOSTON –The Boston Celtics didn’t blink when the Portland Trail Blazers adjusted the Jrue Holiday trade. A fresh look at Holiday’s medicals shifted the final terms. Instead of receiving two second-round picks with Anfernee Simons, Boston settled for a straight player swap. Even so, the Jrue Holiday trade still lands as a win for the Celtics.
Celtics Still Win Jrue Holiday Trade Despite Reworked Details
Aaron Fentress of The Oregonian first confirmed the update. “Holiday’s medicals revealed nothing substantial enough to warrant the trade being negated,” he wrote on X. “However, there was enough there to lead the Blazers to slightly alter the terms of the deal.”
The Portland Trail Blazers trade with the Boston Celtics has been reduced to a straight player swap without the previously reported two second-round picks going to the Celtics, a league source has told The Oregonian/OregonLive.
According to the source, a recent review of… pic.twitter.com/P5KzBABg1h
— Aaron J. Fentress (@AaronJFentress) July 7, 2025
Holiday, 35, plans to train this summer and join training camp in September. Jrue Holiday’s trade frees the Celtics from the final three years of his $135 million extension. In return, they get Simons, who enters a contract year worth $27 million.
Holiday’s Health Nudges Portland to Adjust
Portland’s review uncovered no deal-breaking injuries but signaled enough concern to rework the agreement. If Holiday were perfectly healthy, the Blazers wouldn’t have touched the terms. They clearly felt caution was worth more than the two extra second-round picks.
Still, Holiday won’t sit out. Reports confirm he’s healthy enough to prepare for the season. That’s good news for the Blazers, who will lean on his experience to steady a young roster. But Jrue Holiday’s trade hints that his prime might be fading.
Boston read the room well. At 35, Holiday’s value declines fast. The Celtics knew they had to get ahead of any health slide.
Boston Clears Cap and Adds a Young Scorer
By moving Holiday’s pricey extension, the Celtics gained cap breathing room. The Jrue Holiday trade brings in Simons, a younger guard who can score in bunches. Simons now steps into Boston’s rotation hungry for a payday. He’ll play motivated basketball with free agency approaching.
Losing two second-round picks will barely sting. Keeping them cushions Boston’s asset pool for future deals. Still, the Celtics hold more flexibility now than they did prior to the trade.
No Picks? No Problem for Boston
Many expected Boston to sacrifice leverage this summer. Opponents knew the Celtics planned to offload Holiday’s contract. Even so, they didn’t get fleeced.
This league loves to expose mistakes. When front offices panic, teams lose leverage. That didn’t happen here. Boston stayed patient surveying the market before nailing the Holiday trade.
Smart teams understand timing. Holiday’s medicals made Portland nervous. Boston didn’t beg for compensation. They convinced Portland to push through the trade despite losing those second-rounders.
Years from now, we might see the Jrue Holiday trade as the turning point when Boston kept its edge sharp.
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