ESPN's Shams Charania reports that the Portland Trail Blazers have agreed to trade Anfernee Simons and two second-round picks to the Boston Celtics in exchange for Jrue Holiday.
Many have speculated that Simons could be a trade candidate for Portland this summer, with his contract set to expire after 2025-26. Still, it's shocking that Holiday is the one that the Blazers acquired. To remind you, Boston initially landed Holiday after the Blazers rerouted him from the Milwaukee Bucks following the blockbuster Damian Lillard deal.
The Celtics got their championship with Holiday and will now send him back to Portland. Boston now gets off Holiday's $72 million salary owed in 2026-27 and 2027-28. It's a wise move on their behalf, considering Jayson Tatum is expected to miss most of next season as he recovers from an Achilles tear.
Boston will certainly remain competitive next season, and Simons could also help them in the short term, as they'll need more shot creation and playmaking with Tatum out of the equation.
Blazers continue accelerating their rebuild with Jrue Holiday
It's a hilarious trade for the Blazers because it's a full-circle moment for Holiday. Although Portland was never rumored as a landing spot for Holiday, it makes sense in hindsight.
General manager Joe Cronin has gone on record as saying the Blazers are looking to make the playoffs as soon as next season, and the two-way guard Holiday will help them achieve that goal, which has suddenly just become more attainable.
The Oklahoma City Thunder's Finals run proved how valuable lockdown perimeter defenders are between Cason Wallace and Alex Caruso. Not to mention, Holiday's two championships support that notion as well.
Holiday is 35, so he will be the oldest player on the Blazers roster by a significant margin. But that's actually good thing. One issue with Portland's roster is that they've been straddling the timelines with players like Simons, who can be considered veterans but also part of their young core.
This makes it clear that Holiday is their starting point guard going forward, but with a less murky path for Scoot Henderson to take over that role in the near future.
Overall, we like the trade for the Celtics more than the Blazers. Holiday is a championship presence that will elevate the Blazers' ceiling, but not anywhere close to the needle mover they still lack to become genuine contenders.
At the very least, it puts Portland in a prime position to compete for a spot in the Play-In Tournament in the competitive Western Conference. And it's hard to fault them for wanting to continue trending in the right direction after missing the playoffs four consecutive years.