The Portland Trail Blazers decided to convert Sidy Cissoko from a two-way contract to a standard one. To clear space on their 15-man roster, they waived Rayan Rupert, prematurely moving on from a 21-year-old who had always been viewed as a long-term project.
As the 2025-26 season nears its conclusion, Portland is left wondering whether replacing Rupert with Cissoko was the right decision. They have good reason to second-guess it, and it's less to do with Cissoko and more to do with how well Rupert has played as of late.
Rayan Rupert is already making Portland regret waiving him
After a successful audition on a 10-day contract, Rupert signed a two-way contract with the Memphis Grizzlies. That's proving to be the ideal pairing, with Rupert playing the best basketball of his young career. In fact, he's coming off a shocking performance in which he had a 33-point triple-double in a loss to the Milwaukee Bucks.
Here's the list of players to record at least 30 points, 10 rebounds, 10 assists, and four steals before turning 22 years old: LeBron James, Luka Doncic, Isiah Thomas, Magic Johnson, and... Rayan Rupert.
That's some hilariously elite company. And although Rupert is bound to come back down to Earth, the fact that he's shown flashes of this two-way upside should have Portland's front office concerned that they made the wrong investment.
Rupert has played 11 games in Memphis, averaging 11.3 points, 5.6 rebounds, 1.8 assists, and 1.5 steals during that stretch. While Cissoko has become a fan favorite in Portland as an "Energizer Bunny," Rupert is showcasing a similar two-way impact while providing more on the offensive end, particularly in playmaking and shooting. He's shot 38.8 percent from deep in Memphis, compared to Cissoko's 30.1 percent in Portland.
Rupert was a better fit for a Blazers roster that ranks near the bottom in turnovers and three-point percentage. Between Cissoko and Kris Murray, the Blazers have two redundant role players, and their inability to space the floor puts them at a major disadvantage when they share minutes. Murray has been serviceable as of late, leaving Cissoko's role in question going forward.
The Blazers wouldn't have had that dilemma had they kept Rupert, as he would have provided them with a unique dimension thanks to his versatile skill set as a "Swiss Army Knife." And the scary part is, he's only starting to unlock that potential.
The Blazers have struggled with moves on the margins throughout their rebuild, and it looks like Rupert is the latest example. It's great that he's thriving in Memphis and benefiting from the change of scenery. Still, it's also bittersweet as the Blazers didn't need to move on from a high-upside multi-year project who is already showing that upside elsewhere.