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.
What are Celtics fans really saying about the Jrue Holiday trade?
Well, the Jrue Holiday-to-Portland news didn’t exactly spark the outrage many expected. Instead, Celtics fans online flipped the script and surprised everyone with their reactions. Most didn’t mourn the loss of their veteran guard—they celebrated what they see as a win. “CELTICS WIN BY A LANDSLIDE,” one fan declared, clearly thrilled with the return package. Another chimed in, “Horrific trade for Portland unless they flip Jrue. But Simons has more value, so what are we even doing here?” That vibe? Unexpected but loud.
Now to be fair, Holiday wasn’t just any guy on the roster. He’s been in the league 16 seasons and was crucial in the Celtics’ 2024 championship run. Last season, he put up 11.1 points and 4.3 rebounds a night—not flashy but steady. But next to Anfernee Simons, the numbers do paint a different picture.
Simons, still just 25, has been quietly solid in Portland. Drafted in 2018 out of IMG Academy, he’s been a consistent scorer and playmaker. He averaged 19.3 points and 4.8 assists last season and looks more like a player entering his prime than one winding it down.
Naturally, the trade left some Blazers fans scratching their heads. One asked bluntly, “Why the blazers do this?” Another didn’t hold back at all: “Gave up your elite defender for a point guard who can barely shoot.” But behind the emotion, contracts likely told the bigger story.
Holiday still had two years left on his deal, worth $67.2 million, plus a $37.2 million player option. Shipping him out saves Boston nearly $40 million in taxes and moves them $18 million over the second apron. Meanwhile, Simons is entering the final year of his deal, which gives Boston more future flexibility. Still, fans admit, “Wow! The Celtics get good value but losing his vet presence will hurt.”
So what do you think—who’s the real winner in this deal?
The post Boston Has Unexpected Reaction to Jrue Holiday Exit as Celtics Begin Trade Season appeared first on EssentiallySports.
