The Orlando Magic made Osby, a combo forward from the University of Oklahoma, the 51st overall pick in the 2013 NBA Draft. Osby went though the Orlando Pro Summer League, training camp, and the preseason with the Magic, but veteran big man Solomon Jones earned Orlando's final roster spot. Osby averaged 5.7 points and four rebounds per game in the preseason and played primarily small forward, a position he had not played since high school.
"This was a matter of circumstance and a matter of making a decision that we felt was best for the team," Magic general manager Rob Hennigan said the day after the roster cut. "We'll always do that, always use that philosophy."
The Red Claws are the NBA D-League affiliate of the Boston Celtics. Shams Charania of RealGM reported on October 29th that Boston was interested in adding Osby to its affiliate club, with the possibility of calling him up to the NBA.