A look back at the mayors of Boston

Since Mayor Thomas Menino announced last month that he wouldn’t seek re-election to an unprecedented sixth term of office, a growing list of candidates has made for a crowded race. With speculation as to who will be the Hub’s next mayor, here’s a look back at some of Boston’s most notable.

Pictured, former mayor Ray Flynn, Mayor Tom Menino, and former mayor Kevin White together in the Public Garden.

Josiah Quincy III

Years of service: January 5, 1829 – January 2, 1832

During Josiah Quincy III’s terms in office, Quincy Market was built (and named in his honor), the fire and police departments were reorganized, and the city’s care of the poor was systematized. He also served on the U.S. House of Representatives and as president of Harvard University. Both his son, Josiah Quincy, Jr., and his great grandson, Josiah Quincy, served terms as mayor.

Hugh O’Brien

Years of service: January 5, 1885 – January 7, 1889

Hugh O’Brien was Boston’s first Irish mayor, having emigrated from Irelend in the early 1830s. He was editor of the Shipping and Commercial List, and also served as a Boston alderman.

John F. Fitzgerald

Years of service: 1906–1908, 1910–1914

John F. Fitzgerald, nicknamed “Honey Fitz” for his charming and impish character, was the first American-born Irish-Catholic mayor of Boston and grandfather of former president John F. Kennedy and senators Robert F. Kennedy and Edward Moore Kennedy. Using the slogan “A bigger, busier and better Boston,” Fitzgerald worked to revitalize the commercial importance of the city, especially as a port. Shortly after his election to the presidency, John F. Kennedy renamed the presidential yacht “Honey Fitz” in honor of his grandfather.

James Curley

Years of service: 1914–1918, 1922–1926, 1930–1934, 1946–1950

The legendary James Curley is renowned for his authenticity and immense popularity, particularly among Irish Americans, as well as his Irish Mob connections and corrupt practices. He was re-elected mayor while serving a five-month prison sentence. His campaign for a fifth term (pictured) was unsuccesful when, after returning from prison, he told reporters, “I have accomplished more in one day than has been done in the five months of my absense,” and John Hynes, who had been acting mayor in his absense, was insulted and ran against him, ending his career.

Malcolm Nichols

Years of service: 1926–1930

Nichols was reporter for The Boston Traveler, covering the Massachusetts State House. He was later a political reporter for The Boston Post. Nichols was the last Republican to serve as mayor of Boston to date.

Maurice Tobin

Years of service: 1938–1945

Born in Mission Hill, Maurice Tobin entered politics as the protégé of James Curley. He served in the Massachusetts House of Representatives and on the Boston School Committee before shocking the Boston political establishment by defeating Curley for mayor. During his tenure as mayor, Tobin advocated for the Fair Employment Practices Bill and his administration was marked by efforts to increase unemployment insucance and workers compensation benefits. He went on to serve as governor. In 1967, the Mystic River Bridge was renamed the Maurice J. Tobin Memorial Bridge in his honor.

John Hynes

Years of service: 1947-1960

Hynes was city clerk during James Curley’s fourth term as mayor and served as acting mayor when Curley was jailed for five month. Angered by Curley’s off-hand and disparaging comments about his performance as acting mayor, Hynes challenged and defeated Curley in the 1949 election, and again in the the 1951 and 1955 elections. During his tenure, Hynes oversaw the opening of the Central Artery elevated highway through the waterfront as well as the opening of the Freedom Trail. He also founded the Boston Redevelopment Authority. He, along with John Collins and Kevin White, is credited with the modernization of the city. The Hynes Convention Center is named for him.

John Collins

Years of service: 1960-1968

Born in Roxbury, Collins was elected to the Massachusetts State Senate at the age of 27. During his two terms as mayor, Collins continued the modernization of the city begun by his predecessor, using the redevelopment authority to channel $2 billion of federal money into renewal projects. From this wave of rebuilding and renovation, Government Center rose from a seedy Scollay Square and the waterfront was enlivened as a business and tourist center.

Kevin White

Years of service: 1968–1984

First elected at the age of 38, White was mayor during the racially turbulent late 1960s and 1970s, and the start of the busing crisis. He won the office in a hard-fought campaign opposing anti-busing and anti-desegregation Boston School Committee member Louise Day Hicks. His mayorship is credited revitalizing the waterfront, Downtown, and Financial District, as well as transforming Quincy Market into a metropolitan and tourist destination. More than 20 city hall employees were convicted after a decade-long federal investigation into his administration; White himself was never indicted.

Raymond Flynn

Years of service: 1984-1993

Flynn began his political career representing South Boston during the turbulent busing crisis in the early 1970s, serving as a Democratic member of the Massachusetts House of Representatives. He also served on the Boston City Council before successfully running for mayor in 1983. He was elected to three consecutive terms but resigned in the second year of his third term to become United States Ambassador to the Holy See.