29. Gradey Dick, Toronto Raptors
Checking in at No. 29 on this list, I wouldn't say that Gradey Dick is not a caliber shooting guard in the league, but there are too many questions at the moment about his future. Dick is a talented young player; I'm not sure there would be much pushback on that statement. However, that are real questions about whether he should be a starter heading into just his second season in the league. But it's pretty clear that the Toronto Raptors want to see what they have with their young core. Part of finding that out includes throwing a player like Dick into the open water to see how he'll react.
Heading into the start of the season with Dick as the starter may not be ideal but it could be a good way to see if he's the real deal or if perhaps he may not be a foundational piece of the team's build moving forward.
Through his rookie season, Dick did show some flashes of potnetial. However, he'll certainly have to show a whole lot more if he's going to be able to keep this starting spot all year long - especially if the Raptors have any plans to compete for a playoff spot in the Eastern Conference.