The original jail was built in the form of a cross with four wings of Quincy granite extending from a central, octagonal rotunda with a 90-foot-tall (27 m) atrium.

The wings allowed segregation of prisoners by sex and category of offense, and thirty arched windows, each 33 feet high, provided ventilation and natural light.

Over the years, the jail housed a number of famous inmates including John White Webster, James Michael Curley, Malcolm X, and Sacco and Vanzetti.

Suffragists imprisoned for protests when President Woodrow Wilson visited Boston in February 1919 included Josephine Collins (Framingham), Betty Connolly (West Newton), Martha Foley (Dorchester), Frances Fowler (Brookline), Nellie Gross (Mrs. J. Irving Gross, Boston), and Rosa Heinzen Roewer (Belmont).

It was redesigned by Cambridge Seven Associates[4] and Ann Beha Architects, and reopened in the summer of 2007 as a 300-room luxury hotel with a number of high-end bars and restaurants.