Thirty-eight Boston mayors served terms of office on School Street at this site over a period of one hundred and twenty-eight years, notably John F. Fitzgerald, Maurice J. Tobin, and James Michael Curley. All twenty of the Democrat mayors adopted the donkey as their party's symbol, while only five of the ten Republican mayors utilized the elephant.
In 1828, Andrew Jackson established the Democratic party and ran for president using the populist slogan, "Let the people rule", his opponents thought him silly and labeled him a "jackass". Jackson, however, picked up on their name calling and turned it to his own advantage by using the donkey on his campaign posters. Over the years this donkey has become the accepted symbol of the Democratic party.
The symbol of the Republican party in 1974 was born in the imagination of a cartoonist, Thomas Nast, in Harper's Weekly. Soon other cartoonists used the elephant to symbolize Republicans, and eventually, Republicans adopted the elephant as their official symbol.
Thirty mayors served in the existing building when it served as city hall from 1865 to 1969. Eight others served their terms as mayors on the site from 1841-1865 after Suffolk County Courthouse was converted to a temporary city hall.