John O’Leary was born on January 16, 1947 in Philadelphia, Pennsylvania. He attended Chevrus High School in Portland, Maine, and then Yale, graduating in 1969. He studied as a Mellon Fellow at Cambridge University and received a master’s degree in 1971. O’Leary returned to Yale for law school, earning his J.D. in 1974 and joining the Pierce Atwood law firm in Portland. O’Leary became interested in politics in college and was a campaign volunteer, along with Peter Kyros, Jr., for Ed Muskie. A Democrat, O’Leary served on the Portland City Council from 1975 to 1982, and lost his bid for Congress in 1982. O’Leary also had a friendship with Bill Clinton, a classmate of his at Yale, and was appointed by Clinton as the U.S. Ambassador to Chile in 1998.
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Nicoll, Don, "O'Leary, John oral history interview" (2003). Edmund S. Muskie Oral History Collection. 314.