In June 1991, he married his longtime companion Margaret "Ritchie" Battle (born February 15, 1947), who had made the couple active in the social and cultural life of Pittsburgh. The couple subsequently separated, and, on December 27, 2005, the Pittsburgh Police responded to a call placed by Richard Scaife reporting trespassing at Scaife's residence in the prestigious Shadyside section of Pittsburgh. They arrived to find his estranged wife, pounding on doors and peeking in windows of the couple's mansion. Mrs. Scaife refused to leave the property, and was arrested and charged with defiant trespass.