In high school, he rushed for 3,573 yards with 58 TDs, threw for 1,211 yards with 10 scores and gained 5,855 yards with 394 points. He also made 80 tackles, eight INTs and four fumble recoveries. Bailey was an all-state honorable mention selection in basketball and the state high jump champion as a junior. He is involved in the Redskins All-Stars program, encouraging kids to get involved in community service and volunteerism. He also participates in the annual Redskins Season Kickoff Cruise to support the Darrell Green Youth Life Foundation and sponsors a child at the foundation's “Christmas with the Redskins” party each year. Bailey and his wife, Hanady, live in Sterling, VA, with their son, Keevan.