Celtics maximize Holiday return, Blazers leave us confused
The trade that sent Jrue Holiday from Boston to Portland won't dominate headlines like Kevin Durant's move to Houston, but it's arguably more fascinating and certainly more surprising.
Trail Blazers receive: Jrue Holiday
Celtics receive: Anfernee Simons, two 2nd-round picks
What are the Blazers doing?
Holiday remains one of the best defensive players of his generation and is among the most respected people in the league, so it's not inconceivable that a rebuilding team would want him around its youngsters. What's hard to square is the price Portland paid for him.
With Holiday having lost a step on the defensive end and his offensive impact limited at this stage of his career, many assumed the Celtics would need to attach draft picks to find a team to take the three years and $104 million left on the 35-year-old's contract. Had Portland acquired Holiday along with some future-minded assets, no one would've batted an eye. But that's not what happened. Instead, the Blazers surrendered those future-minded assets in the form of multiple picks and a 26-year-old 20-point scorer (Simons).
Simons was clearly the odd man out as a one-way player on an expiring contract in the same backcourt as Shaedon Sharpe and Scoot Henderson, and he's the last holdover from former GM Neil Olshey's regime. Still, it's a strange transaction for a club in Portland's position. While the Blazers likely didn't want to watch Simons leave for nothing as a 2026 free agent, they had ample time to figure out an exit plan congruent with their timeline.
Perhaps Portland's 23-18 record in the second half of the season convinced the front office that the team's ready to make a leap. But the Western Conference is stacked, and the Blazers will be hard-pressed to make the play-in tournament. Plus, a vastly improved defense spurred that second-half charge, and this group still desperately needs more offensive juice. That makes Simons' departure in this particular deal even more confounding.
Celtics get cap relief, flier on Simons
The Celtics' 2025-26 season became a bridge year the moment Jayson Tatum crumpled to the Madison Square Garden court with an Achilles injury during the second-round playoff series with the New York Knicks in May.
Boston's short-term mission was clear: unload Holiday's contract without taking back any long-term salary. That move would allow the Celtics to duck both aprons beginning in 2026-27 without breaking up their $620-million championship duo of Tatum and Jaylen Brown. Mission accomplished.
The fact that Boston managed to do that (and shave $41 million off their tax bill) while acquiring a couple of second-rounders and taking a flier on Simons was a stroke of genius by team president Brad Stevens.
Simons has defensive warts, but he's averaged nearly 21 points and five assists over the last three years while shooting 50% inside the arc, 37% from deep, and 90% from the free-throw line. He's a professional scorer and improving playmaker who should thrive with more talent around him, even if it's in a reduced role.
No one's expecting Simons to suddenly become a two-way force. However, there's enough upside for this to be an extremely intriguing acquisition for a quality organization like the Celtics.
Joseph Casciaro is theScore's lead NBA and Raptors reporter.