1874 – Boston Mayor James Michael Curley.

James Curley’s father emigrated from Ireland at age of fourteen. Curley first won the mayoralty in 1914, succeeding his arch-rival John “Honey Fitz” Fitzgerald. (Fitzgerald was the maternal grandfather of John F Kennedy.) Born to an Irish immigrant and petty criminal father, Curley was no saint himself. Over a lengthy career, he served two jail terms, the latter being for corruption in 1947 while in his final term as mayor. Curley spent five months in jail before his sentence was controversially commuted by President Truman, who finally pardoned him in 1950. On his release from prison, Curley returned to the mayoral role until 1950.

As his consistent election victories suggest, Curley was a master politician and media player who was exceptionally popular with his constituents.

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