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The Warden's House on Monument Street is a remarkable work of architecture and a unique reminder of the history of justice and injustice in Baltimore. The Warden's House was built as part of a larger city jail designed by local architects Thomas and James M. Dixon and erected between 1855 and 1859. Originally, this structure served as both a gateway through the jail's perimeter wall and a residence with the warden's apartment to the structure's west side and a suite for a clerk on the east. Unsurprisingly, it more closely resembles a fortress than a house with battlements on the towers, projecting turrets, and lancet windows.

The main jail was altered beyond recognition and the wall was torn down around the mid-1960s take make way for the expansion of the Baltimore City Detention Center. But the Warden’s House survived and won recognition for its unique Gothic design when the Baltimore Commission for Historical and Architectural Preservation made it a local landmark in 1986. The site itself has an even longer history as the site of the city's first jail erected in 1800.

In the late eighteenth century, a local sheriff controlled the city jail and, according to John H.B. Latrobe, revenue from the jail's operation made up "most lucrative part of his income." For the new jail, the state legislature established a new system where the warden worked under the supervision of a board of visitors and was paid a fixed salary. In 1832, Latrobe called it "on the whole, an excellent and well conducted establishment."

However, most Baltimoreans found no justice or humanity here. Early prisoners included famed abolitionist William Lloyd Garrison who spent seven weeks there in 1831. In October 1832, the jail held seventy-five people: forty as "debtors" and thirty-five on criminal charges. The latter group included two eleven-year-old Black boys charged with setting fire to a lumberyard.

By the early 1850s, reform-minded observers sought a new jail where the city could avoid mixing children with "old and hardened prisoners." For example, in February 1851, a grand jury reported on the "inappropriateness of the structure" and the "limited capacity" of the building (then holding over 240 people) to the judges of the City Court. In 1855, a design competition awarded the project to Thomas and James M. Dixon, construction began in 1857, and, by December 1859, the new building was complete. Supervised by warden Capt. Thomas C. James, the new jail had three hundred cells in two separate wings. The Sun observed: "Baltimore can now boast of a prison in point of appearance, stability and comfort, second to none other in the country."

Despite the physical improvements, the jail remained dedicated to an awful purpose. From 1859 to 1864, the Baltimore Jail was used to hold hundreds of “runaways” along with Marylanders, both white and Black, who assisted enslaved people as they fled to freedom. At the time, a number of private slave jails operated around the harbor but, for a fee, slaveholders could also leave the men and women they held at the city jail.

The buildings where these men and women were held remained almost unchanged for a century until they were transformed in the 1960s. The Warden's House is one of the only jail buildings that has been preserved. The gateway had long since been converted into the warden's living room. In 1974, converted into offices while keeping the building's distinctive interior intact.

At present, change is coming to the Baltimore Jail once again; threatening the Warden's House and the nearby 1898 Maryland Penitentiary with demolition. In July 2015, Governor Larry Hogan announced the immediate closure Baltimore jail following years of concerns and controversy over conditions for inmates and corrections officers. In the spring of 2016, the Maryland Division of Corrections (MDC) released their preliminary plan for the demolition of the Baltimore City Detention Center including this local landmark. Planning is now underway but preservationists are still working to keep this unique reminder of Baltimore's history from disappearing forever.