Trevor Bailey was born in the district of Broadgate in the parish of St. Mary on the island of Jamaica. He attended the Broadgate All Age School, the Richmond Secondary School, and St. Mary High School. After graduating, he went to the Edna Manley College for the Visual and Performing Art in which he obtained a bachelor's degree in Painting and Sculpting. After his graduation, he taught at the St. Andrew high school for girls and Ewarton High School for fourteen years, he also did extensive work with the Jamaican Cultural Development Commission. (J.C.D.C.) Mr. Bailey had a major exhibition at the Edna Manley College for the Visual and Performing Arts, where he was awarded the Ronald Moody Scholarship for the most outstanding student from the sculpture department that year. He also exhibited at the Mutual Life Gallery and many others. He then migrated to the United States of America where he taught at the Eagle Nest Charter School, the Nine Muses Art Center and the Circle of Friends and Stars Art Center. He also exhibited at The Frank, Art Serve, The Tamarac Library, Rebels Art Center, Studio 18, and many others. Trevor Bailey is still an active painter and sculptor.