As Curley came of age, Boston politics were marked by growing Irish political power in opposition to traditional Yankee Protestantism. Curley involved himself in the local Roman Catholic church and the
Ancient Order of Hibernians, a
fraternal benefit society that assisted Irish immigrants. He acquired a reputation as a hustler who was willing to help others get ahead. Curley gained experience in the traditional practices of
ward politics such as knocking on doors, drumming up votes, and taking complaints. He ran for a seat on the Boston Common Council in 1897 and 1898, but failed to achieve the Democratic nomination in ward caucuses each year. Curley claimed he was denied victory by corrupt vote counting, rigged against him because he was outside the
political machine. Curley was successful in 1899 by joining the machine faction controlled by Charles I. Quirk. In his first two years on the Council, Curley placed roughly 700 people into
patronage positions. His reputation as an urban populist earned him the unofficial title "Mayor of the Poor."
Boston Common Council (1900) In 1900 Curley became the youngest
ward boss in Boston at 26 years of age. He obtained through political maneuvering positions on Boston's Board of Aldermen. Curley became a member of the Boston Common Council in 1901, representing the seventeenth ward. Curley later recounted stories of the ward's poor and needy lining up outside the club's office to ask for work or subsistence.
Boston Board of Aldermen (1905–1909) Curley served on the
Boston Board of Aldermen from 1905 until 1909, Curley's first public notoriety came from being elected to Boston's board of aldermen in 1904 while imprisoned on a
fraud conviction. The charge resulted after Curley and the unrelated Thomas Curley had helped two applicants in their district
cheat on federal civil service exams for postmen, by criminally
impersonating the applicants and taking the exams for them. Though the incident gave him a dark reputation in Boston's non-Irish circles, it aided his image among the
Irish American working class and poor because they saw him as a man willing to stick his neck out to help those in need. During that election, his campaign slogan was, "he did it for a friend." He also quickly gained a reputation for taking
kickbacks in exchange for his support. In January 1909, after the board had been unable to garner the required consensus to elect a new
board chairman, Curley briefly served as the acting chairman in the interim. On January 26, 1909, the board elected Frederick J. Brand its permanent chairman.
U.S. Congress (1911–1914) In 1910, while a member of Boston's board of aldermen, Curley challenged U.S. Representative
Joseph F. O'Connell, a fellow Democrat. His first preference was to run for mayor of Boston, but former Mayor (and czar of Boston Irish politics)
John "Honey Fitz" Fitzgerald ran for the office. In exchange for Curley staying out of the mayoral race, Fitzgerald promised not to run for re-election after a single four-year term. In the previous election for the seat, O'Connell won by a four-vote margin over his Republican opponent, ex-City Clerk
J. Mitchel Galvin. In a three-way primary among O'Connell, Curley, and O'Connell's predecessor
William S. McNary, Curley defeated O'Connell and McNary. After winning the nomination of the Democratic Party, Curley went on to win the general election by a substantial plurality over Galvin, who was again the Republican nominee. ==First mayoralty (1914–1918)==