McCaffrey, from Providence, Rhode Island started his career as a US Army photographer while serving in Hawaii in 1964. He studied photography at the Franklin Institute of Boston, and after graduating in 1967, he worked as a photographer and photo lab technician at Brown University.
Richard moved to the San Francisco Bay Area in 1973. During the 1970s and 80s, he freelanced for magazines such as Rolling Stone, Billboard, Creem Magazine, and many other publications. He was Chief Photographer for “BAM, The California Music Magazine” from 1976 - 1986 and also worked with Bill Graham Presents, bands, and record companies. In 1979, he co-founded “Eye Gallery,” a non-profit photo gallery, Community lab, and studio in the Mission District of San Francisco, and was Board Chairman from 1982 to 1984.