Tony DeRosa was a close associate of Howard “Buddy” Jacobson and a figure in the New York nightlife and horse racing circles of the late 1960s and 1970s. Known as a loyal but financially troubled friend, DeRosa owed Buddy money after Jacobson lent him funds to invest in a swingers-style ski resort lodge venture that ultimately failed. Despite the debt, the two remained close, and DeRosa later became involved in Buddy’s dramatic 1980 escape from the Brooklyn House of Detention, helping facilitate elements of the jailbreak and the early stages of the fugitive flight. His role tied him directly to one of the most sensational episodes in Buddy Jacobson’s life.