Formerly a police officer, Winchester pursued music as a hobby in
Wilmington, Delaware. He turned to music full-time after an appearance at the 1958
Newport Jazz Festival. He was soon working with some of the top names in jazz, making his debut recording with pianist
Ramsey Lewis. Winchester recorded a handful of albums as a leader, and made sideman appearances with the likes of saxophonist
Oliver Nelson, and organists
Jack McDuff and
Shirley Scott. Most of his recordings were with
Prestige Records. Critic
Scott Yanow has suggested that while Winchester's playing was strongly influenced by
Milt Jackson, he "did not stick around long enough to carve out his own original voice" on the vibraphone. ==Death==