Former City of Boston Mayor Raymond Flynn spoke about his ten years as Mayor (1984 to 1993) and his four years as Ambassador to the Vatican under President Clinton (1993 to 1997).  He spoke elegantly about his family emigrating from Ireland and then living in Boston's South End (where he still lives) and starting from the bottom. Asked why the New York Times rated him as the most popular and successful Mayor in Boston's History, Mr. Flynn noted that it was because "he cared about and knew the local people".  Mayor Flynn spoke about his early days when he went to Providence College with a basketball scholarship and became an All-American basketball player, later playing briefly for the Celtics.

As Mayor of Boston, Mr. Flynn spoke about some of the problems he helped solve, including Boston's serious political divide from the bussing crisis, which racially divided neighborhoods; the City of Boston experiencing Urban Flight to the suburbs: the City of Boston running a large deficit financially, and homeless people on drugs at Massachusetts  & Cass Avenues. He was proud of helping the homeless, even occasionally bringing some home in the winter months. BHS members found Ray Flynn a principled and caring person, unlike anybody they have known, despite the profile of his political position.