Charles St Jail History

By Dan Murphy

For Tuesday’s third and final Twilight Talk presented by Historic New England and the Victorian Society in America/New England Chapter at the Harrison Gray Otis House, award-winning documentary filmmaker and journalist Joseph McMaster recounted the history of the Charles Street Jail, from its origins as a state-of-the-art facility through its decline and eventual rebirth as a luxury hotel.

McMaster, who penned the recently published book “Charles Street Jail,” discovered the building while living in Beacon Hill in the late ‘80s and commuted to Harvard Square for work on the MBTA Red Line. “I didn’t even know it was a jail,” he admitted.

The jail, which was built between 1848 and 1851, was the brainchild of Boston architect Gridley James Fox Bryant and Rev. Louis Dwight, a prison-reform activist and founder of the Prison Discipline Society, an organization that collected facts and statistics on jails and prisons via annual visits to the facilities. Bryant left his imprint on “hundreds” of buildings throughout the city, including the Arlington Street Church and the old Boston City Hall, yet he died destitute and virtually unknown, McMaster said.

The cost of the building was estimated at between $409,000 and $493,000, including creating the landfill parcel on which it was built, and the jail was designed with around 30 windows to bring in as much light and fresh air as possible.

In 1902, a wing of the building was enlarged, allowing for a hospital upgrade; new kitchen where bread was baked fresh each day for the prisoners; and an auditorium that accommodated movie screenings and religious services.

The jail had a good reputation for a number of decades under a succession of elected sheriffs who lived on the premises, and since it wasn’t a prison, the jail temporarily housed men, women and children as they awaited court proceedings.

“Anybody who got into any kind of trouble in Boston came through the Charles Street Jail,” McMaster said.

James “Whitey” Bulger was incarcerated there for the first, but McMaster said contrary to popular belief, there is no evidence the jail ever housed Malcolm X or Nicola Sacco and Bartolomeo Vanzetti – two Italian-born anarchists convicted of armed robbery and murder and executed at the Charlestown State Prison in 1920 amidst worldwide opposition. Baseball legend Babe Ruth toured the facility on a visit to Boston and noted that it seemed more like a hotel than a jail.  Over time, the facility fell into a state of severe disrepair as riots and prisoner escapes became more frequent. Elmer “Trigger” Burke, a New York contract killer who had a hand in the Great Brink’s Robbery of 1950, was among those who escaped (but was later recaptured) from the jail. Meanwhile, newspapers began calling attention to the inhumane conditions at the facility while holding the city accountable, and a civil suit was eventually brought against the jail by inmates claiming “cruel and unusual punishment.”

In 1973, the U.S. District Court ruled that due to overcrowding, the jail was in violation of the constitution rights of the prisoners housed therein, yet it remained in operation for nearly until 1990 when the nearby Nashua Street Jail opened.       The jail then sat vacant for around a decade until Massachusetts General Hospital purchased the building and subsequently used it for storage. A number of proposals for repurposing the facility were considered, including possible reuse as a pet hotel, before the summer of 2007, when it reopened as the 300-room, luxury Liberty Hotel – a name that wryly recalls its past use. “It’s a pretty remarkable transformation,” McMaster said. “I don’t think anybody who spent any time here before could’ve ever imagined what it has become today.” McMaster’s “Charles Street Jail” is published by Arcadia Publishing, and all proceeds go to the West End Museum. Visit to purchase the book.

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