3. Jerami Grant
The Blazers never should have signed Jerami Grant to his five-year, $160 million contract last summer. This offseason is an opportunity for a fresh start as they focus on clearing cap space. It would also open up more playing time for their younger players, including forwards Jabari Walker and Toumani Camara.
Moving Grant may be the most challenging of the five players mentioned, with questions surrounding whether he is a positive or negative trade asset due to the size of his contract. Grant's salary may limit the number of teams that would be willing to take him on - it would likely have to go to a team looking to add another piece to get over the playoff hump. They would need cap space or a salary filler they can trade with fewer years remaining on their contract than Grant.
Like Simons, Grant is one of the team's best shooters. Even if you are a rebuilding team, it's always tough to trade someone who is arguably your best player, nonetheless someone who plays a position of need. Still, Grant is 30 years old and doesn't fit their rebuilding timeline. While a great NBA player, he's not a star who can move the needle for Portland anytime soon.
The Blazers want to keep their cap flexibility open in the coming years, and dumping Grant's salary would be a great start.