The Boston Celtics shocked the NBA world once again this offseason by trading defensive stalwart Jrue Holiday to the Portland Trail Blazers in exchange for the high-scoring Anfernee Simons and two second-round draft picks, according to ESPN reports on Monday night.
On paper, the trade addresses some pressing concerns. Holiday, a two-time NBA champion and one of the most respected veterans in the league, was set to earn $32.4 million this upcoming season as part of a four-year, $134 million extension signed earlier this year. Shedding that contract opens up substantial flexibility for Boston, which is reportedly aiming to cut $40 million in luxury tax obligations.
In return, Boston receives 26-year-old Simons—an explosive scorer with a smooth shooting stroke and a career 38.1% from beyond the arc. He’s coming off a season where he averaged 19.3 points per game and now joins a Celtics roster that already leans heavily on perimeter offense.
But here’s the big question: Was this trade more about financials than basketball?
Simons is on an expiring deal, meaning the Celtics could risk losing him in free agency next summer if they don’t make a compelling offer. And while he’s younger and arguably fits a faster-paced, offense-first model, he’s never played a postseason game. In contrast, Holiday was a clutch performer on both ends of the floor, who brought leadership, playoff composure, and relentless defense.
That’s the part that’s hard to measure. While Simons may fill it up on the scoreboard, will the Celtics miss Holiday’s poise in late-game situations, his ability to lock up the opponent’s best guard, and his calming presence in the locker room—especially with Jayson Tatum expected to miss significant time with an Achilles injury?
From Portland’s angle, the move is a savvy play to stabilize their young, rebuilding team. Holiday brings mentorship for Scoot Henderson and Shaedon Sharpe, and provides the Blazers with a respected leader as they continue to shape their identity post-Lillard. Even if Portland isn't contending this year, Holiday's presence could help accelerate the development of their young stars.
This trade might work out well for both sides—but it's not without risks. For Boston, it’s a gamble on potential over proven leadership. For Portland, it’s a bet that Holiday’s best years aren’t behind him.
So now the question is: Did the Celtics just outsmart the league—or will they regret letting Jrue walk away after just one season and a title?
What do you think—did Boston make the right call, or should they have held onto Holiday? Let us know your take on this blockbuster trade.
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