Milk started a romantic relationship with Jack Galen McKinley, and recruited him to work on conservative Republican Barry Goldwater's 1964 presidential campaign. Their relationship was troubled: McKinley, aged 16, was 17 years younger than Milk, and prone to depression and frequently threatened to commit suicide if Milk did not show him enough attention. To make a point to McKinley, Milk took him to the hospital where Milk's ex-lover, Joe Campbell, was himself recuperating from a suicide attempt, after his lover—a man named Billy Sipple—left him. Milk had remained friendly with Campbell.
Milk and McKinley were among the thousands of gay men attracted to San Francisco. McKinley was a stage manager for Tom O'Horgan, a director who started his career in experimental theater, but soon graduated to much larger Broadway productions. They arrived in 1969 with the Broadway touring company of Hair. McKinley was offered a job in the New York City production of Jesus Christ Superstar, and their tempestuous relationship came to an end.