Born and raised in Houston, Texas, Haywood played as a teenager in a high school band with Arnett Cobb.
His first professional engagement was with Chester Boone's band in 1934, followed by an extended run with Milt Larkin (1935–42); during his tenure in the band the reed section included Illinois Jacquet, Tom Archia, and Eddie "Cleanhead" Vinson in addition to Cobb.
[1] Haywood also played with Floyd Ray and Lionel Hampton around the turn of the decade.
Toward the middle of the 1940s Haywood moved to California, served in the Army during World War II, and following this joined Saunders King in 1948.
In the late 1960s, he contributed arrangements to a big band led by Sonny Franklin; among the participants were Tom Archia and Don Wilkerson.