1. Jerami Grant
Of the players mentioned, Jerami Grant is the one who clearly doesn't fit the Blazers' rebuilding timeline at 30 years old. The Blazers don't need to trade him this offseason if no trade comes to fruition, but it would be wise if they explore all options with Grant. He's still owed over $100 million and has a player option worth $36.4 million for the 2027-28 season. Although the contract may seem better due to the projected increase in salary cap, Grant's production may be declining towards the end of his contract.
In other words, he may be at peak trade value this summer. While it's a ton of money to pay Grant, some teams are interested in acquiring the Blazers forward, most notably linked to the Los Angeles Lakers. Teams seem willing to part with significant trade pieces to acquire Grant, which suggests that his contract isn't a negative asset, as many initially thought.
Another reason the Blazers should pursue a Grant trade this summer is that most of the free agency and trade market has dried up—players like Paul George, DeMar DeRozan, and Dejounte Murray, to name a few, have already found different landing spots. Grant is one of the best remaining players available for trade, and the Blazers should use that leverage to their advantage.