After trading for 35-year-old Jrue Holiday, it's clear that the Portland Trail Blazers are looking to make the playoffs in 2026. They sent 26-year-old Anfernee Simons to the Boston Celtics, who better fit their timeline but was on an expiring contract.
Portland has missed the playoffs for four straight seasons but took a significant step towards ending that drought this season in the form of a 15-win improvement, finishing with a 36-46 record. They were surprisingly right in the conversation for making the Play-In Tournament after a midseason turnaround primarily catalyzed by their young core.
Making the playoffs is now a 'reasonable expectation' for the Blazers
Following his extension, general manager Joe Cronin said that making the playoffs in 2025-26 is a "reasonable expectation". That hinted at some win-now move being made, as it was clear that the Blazers, despite their improvement, were still a piece away from that being realistic. Now they add that piece in two-time NBA champion Holiday, who was previously on Portland's roster before being traded to the Celtics.
He's coming off a relatively down season in which he averaged 11.1 points, 4.3 rebounds, 3.9 assists, and 1.1 steals on 44/35/91 shooting splits. But Holiday is the type of two-way player that always impacts winning more than the stats indicate.
The bigger question surrounding Holiday is his contract. He's set to make $32.4 million next season and $34.8 million in 2026-27, with a $37.2 million player option in 2027-28. That limits Portland's flexibility going forward, but it's also not much more than they'd likely have to pay Simons with his looming extension.
Holiday is a better fit for Portland than Simons
Holiday is not only a better overall player than Simons but also fits Portland's roster much better. There was too much overlap in their backcourt trio of Simons, Scoot Henderson, and Shaedon Sharpe. It was an extremely poor defensive trio, with Simons having the worst defensive rating on Portland's roster for multiple seasons.
By extending Chauncey Billups, Cronin and the Blazers are committed to his vision of being a gritty, defensive-minded team. That was never going to come to fruition with Simons still on the roster. He had to be the odd man out with his expiring deal and Henderson and Sharpe's tantalizing ceilings. The Blazers already have that hard-nosed defense established in their frontcourt, but now it's a balanced attack with Holiday leading the charge out on the perimeter.
With this trade, it's clear Portland is tired of being on the outside looking in of the playoffs. And it's a win-now move, but it's not overly aggresive to the point where they sacrifice their future.