Gregory is an actor/singer/dancer from Nassau, Bahamas. He is currently playing the role of Aaron Burr in the Chicago company of Hamilton. On Broadway, he was the standby for Washington and Burr. Other credits include Taboo on Broadway, produced by Rosie O'Donnell; the off-Broadway hit Zanna Don't, where he created the role of Zanna, Miracle Brothers at the Vineyard Theatre (directed by Tina Landau), and the World Premiere of Neil Berg and Robert Schenkkan's The 12 at the Denver Center for the Performing Arts. Gregory was a finalist on WB's television show Popstars. TV credits include a guest-starring role on the CBS sitcom Whoopi. He is a graduate of Carnegie Mellon University.