Williams dominated Madison High hoops in the early 1970s. By his freshman year, he already stood tall, with outstanding moves, a fantastic shot, a terrific knowledge of the back board action, and could play the crowds. However, due to his poor attendance at Madison, Williams completed high school at a prep school, Glen Springs Academy, in Watkins Glen, New York. The book "Heaven Is a Playground" discusses, among other things, the education of Fly Williams. According to "Loose Balls" author Terry Pluto, Williams took the nickname in homage to singer Curtis "Super Fly" Mayfield. Williams was known for his play at Rucker Park and The Hole (Brownsville).