It’s official—Jrue Holiday is heading back to Portland. According to ESPN’s Shams Charania, the Trail Blazers and Celtics finalized a deal Monday night that sends Holiday to Portland in exchange for Anfernee Simons and two future second-round picks. But here’s the kicker—this isn’t just about Holiday packing up. As Charania hinted, “the deal is only the beginning for the Celtics this offseason.” And with that, the plot thickens.
Naturally, Boston fans thought the championship squad would stay intact for at least another season. Instead, the front office is turning up the heat. “An extremely active offseason begins for the Celtics with the trade of Jrue Holiday, who played a critical role in Boston’s 2024 NBA championship,” Charania posted on X. Even more interesting, he added, “The Celtics remain engaged in trade talks surrounding multiple key players on the roster.” Translation? No one’s spot is safe right now.
To be fair, Holiday’s journey has been wild. After the Lillard blockbuster landed him briefly in Portland last season, Boston swooped in before he ever suited up. Now, after helping the Celtics lift the 2024 title, he’s circling back—this time possibly for real. Still, that “possibly” matters. Holiday could make a significant impact with the Trail Blazers next season … if the Blazers opt to keep him this time.
BREAKING: The Boston Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons and two second-round picks, sources tell ESPN. pic.twitter.com/2ycXQicGkT
— Shams Charania (@ShamsCharania) June 24, 2025
Meanwhile, Boston fans seem caught between disbelief. No one expected this twist.
(Developing story …)
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