O'Connor first became involved in politics as a community activist in Roxbury. From 1951 to 1970 he was a member of the Massachusetts House of Representatives. During his tenure as a state representative, O'Connor's interests included finance, consumer protection, housing, and supporting the policies of Democratic governors Paul A. Dever, Foster Furcolo, and Endicott Peabody. O'Connor was a staunch supporter of the Furcolo administration and backed the governor's proposal to create a 3% sales tax. In 1960 Furcolo appointed O'Connor to a six-year term on the Boston Licensing Board. In 1956, O'Connor helped obtain the release of a Dorchester mother of four who was arrested by Boston Police at 4:30 am for parking violations. After the incident, O'Connor a bill that would make it a crime for police to serve parking warrants between 10 pm and 7 am. In 1958, O'Connor supported John F. Thompson, a friend and fellow World War II veteran, in his quest to become Speaker of the Massachusetts House of Representatives. O'Connor supported Thompson in spite of opposition from many powerful Democrats including John F. Kennedy, Ted Kennedy, and Endicott Peabody. On May 31, 1960, O'Connor purchased a vacant lot abutting his funeral home for $300 at a city auction. The sale was voided after William H. McBain, who represented abutting business owner, filed a complaint. McBain claimed that he had the site under observation on the morning the auction was to take place, but did not see anyone on the lot. The Real Property Board voided the sale and order that a second auction be held. McBain, however, withdrew his complaint and did not bid at the second auction because he wanted to keep the good will of his state representative, as there were bills under consideration that could hurt the business he worked for. O'Connor purchased the property at the second auction for $800. The incident was brought before the Boston Finance Commission in 1962 after Real Property Commissioner James J. Sullivan cited the auction as one of the complaints he had to handle since taking office. No action was taken against O'Connor, however, the Finance Commission demanded the dismissal of City Auctioneer John J. McGrath and the abolition of the City Auctioneer's position. On February 4, 1970, O'Connor was convicted of willful failure to file Federal income tax returns. According to prosecutors, O'Connor did not file income tax returns for the years 1962 and 1963, during which time he had a total income of $44,000. He was sentenced to five months in jail and fined $10,000.
After his retirement, O'Connor resided at his former summer home in Hull, Massachusetts and at the home of his longtime partner in Nokomis, Florida. He died on May 5, 2011 in Sarasota, Florida at the age of 86.
