Fold: Doug McDermott
McDermott has seen his role with the Spurs diminish each season, and he might be nearing the end of the road in the 2-1-0. He is logging his fewest minutes per game since his rookie go-round in the league, and at 32, he is the oldest player on a rebuilding roster that has prioritized development in recent years. The youth movement is full speed ahead, and the tried-and-true marksman deserves a chance to make the playoffs.
Holding onto Osman may mean the front office has to be open to the idea of trading McDermott. Every postseason hopeful desires more long-range shooting and depth insurance to round out their roster. He checks each of those boxes, and the tenth-year forward is burying a career-high 47.5% of his three-point attempts through 17 games. San Antonio should be able to capitalize while his value is trending in the right direction.