The Raptors should develop Gradey Dick
The player that the Toronto Raptors should start at shooting guard is second-year wing Gradey Dick. The former Kansas marksman grew by leaps and bounds down the stretch last season and showed he is ready for another step forward in Summer League before suffering a minor injury.
The Raptors may be tempted to start Bruce Brown at the 2 and push for a Play-In Tournament berth at the start of the season. If the goal is to win as many games as possible this season it's possible Brown does that, but his poor fit in a starting lineup with Scottie Barnes and Jakob Poeltl won't necessarily propel them up the standings.
Gradey Dick may be the best fit in the starting lineup right now with his high-volume shooting ability, even if his defensive game needs development. That's also why the best path to winning the most games long-term is to give Dick the starting spot and all-important minutes to work on that defensive game.
The more tape the Raptors can show him to address his defensive mistakes the better. The more times he can try to stay with his man through hard screens and off-ball movement the better he will get at navigating them. On offense he's ready to step up, and defensively the best way to develop him is to play him.