John "Honey Fitz" Fitzgerald

Honey Fitz was the incumbent mayor of Boston leading into the first of James Michael Curley's four non-consecutive terms. In 1910, Honey Fitz convinced Curley not to run for the mayoralty by promising to allow him to run in the following term; Honey Fitz then broke this promise when in 1914 he runs anyway with the backing of the mafia-esque ward bosses - he was eventually forced to withdraw from the race after Curley blackmailed him with evidence of his affair with the cigarette girl Elizabeth "Toodles" Ryan.