Osby was selected with the 51st overall pick by the Orlando Magic in the 2013 NBA draft.[1] In July 2013, he joined the Magic for the 2013 NBA Summer League. On September 27, 2013, he signed with the Magic.[2] However, he was later waived on October 25, 2013.[3]
On November 4, 2013, the Fort Wayne Mad Ants, the D-League affiliate of the Magic, traded Osby's rights to the Maine Red Claws.[4] On January 22, 2014, he was waived by the Red Claws due to a season-ending shoulder injury.[5]
In July 2014, Osby re-joined the Orlando Magic for the 2014 NBA Summer League.[6] He later signed with the Le Mans of the LNB Pro A for the 2014–15 season on July 25.[7] After being ruled out for four months in late November with another shoulder injury,[8] Le Mans and Osby finally parted ways on January 5, 2015.[9] On February 5, 2015, he was reacquired by the Maine Red Claws.[10] On April 20, 2015, he signed with Indios de Mayagüez of Puerto Rico for the rest of the 2015 BSN season.[11] On May 29, 2015, he parted ways with Indios de Mayagüez.[12]
On July 28, 2015, he signed with the French club JSF Nanterre.[13] He left Nanterre after appearing in four league games, and on October 21, 2015, he signed with Maccabi Rishon LeZion of Israel.[14] On December 7, 2015, he left Rishon LeZion and signed with Maccabi Kiryat Gat for the rest of the season.[15]