Known as one of the most eclectic trumpet players in New York City, Bailey is an in-demand musician and teaching artist in all forms of jazz, R&B, pop and classical music. He became a member of the Buddy Rich Band while still in college, and his career has included tenures with Ray Charles, Ray Barretto and New World Spirit, The Woody Herman Orchestra and Frank Sinatra, Jr. He has performed and recorded with James Moody, Kenny Burrell, Dr. Lonnie Smith, Barrett Deems and many others. His work with Arturo O'Farrill won two Grammy Awards, for the albums The Offense of the Drumand Cuba - The Conversation Continues. He has played on more than 75 albums and, as a jazz educator, has taught at the University of Miami and Florida International University.