William S. O'Sullivan

William S. O'Sullivan (January 31, 1928 — March 28, 1971) was an Irish-American loanshark and longtime enforcer for Donald Killeen, the head of the Irish mob in South Boston, Massachusetts. O'Sullivan also acted as a mentor to a young James J. Bulger, who grew up to become the leader of Boston's Winter Hill Gang.

O'Sullivan was born in South Boston. He moved to the Savin Hill section of Dorchester with his wife, Mary, with whom he had six children. He worked for the state Massachusetts Department of Public Works until he was injured on the job in 1970 working on an MBTA tunnel at South Bay, Boston in South Cove. He had also previously worked as a bartender in South Boston. His wife Mary worked at Girl's Town (Girls Town of Somerville) on Morrissey Boulevard. She later told reporters, "Bill was a kind father. He wasn't strict with the children. He like young people, however, he was against... long hair... he didn't think it looked right."

They lived in a home at 300 Savin Hill Avenue. After her husband was murdered Mary professed not to have any knowledge on why her husband was shot to death, practically on the front steps of their home. She stated to the press that she was convinced that her husband's murder was not "one of those gangland slayings". She would later say that William was a "quiet man", a "fine husband" and a "wonderful father, and that he (wasn't) the type of person that you would associate with gangsters." Contrary to statements made by his wife, FBI documents report that O'Sullivan had a reputation as a "tough guy" and a prosperous loanshark because he was a close associate of Stephen Flemmi and Frank Salemme.

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