Winfield was born on May 22, 1939 in Los Angeles, California. He studied at the Manual Arts High School,at Los Angeles City College, at University of Portland, at Stanford University, and at the University of California at Los Angeles. Winfield was openly gay. He was partners with Charles Gillan, Jr. from 1972 until his death in 2002. Winfield died on March 7, 2004 after having a heart attack, a complication from his diabetes in Los Angeles, California, aged 64.