The Writings of Thomas Smallwood

A long-forgotten Black abolitionist who liberated captive workers by the wagonload, brilliantly satirized slaveholders, and gave the underground railroad its name.

A Penguin Classic

Thomas Smallwood was a shoemaker by day and an organizer of mass escapes from slavery by night. Twelve years after purchasing his freedom, Smallwood took to the press and, over a sixteen-month stretch starting in 1842, pseudonymously published newspaper dispatches ridiculing and excoriating enslavers by name and offering sobering reflections on the depravity of slavery. With the pen that Smallwood called his “lash,” he leveraged mockery to flip the oppressive racial power structure of America. These dispatches, in which Smallwood was the first to use "underground railroad" in print, are the only accounts of escapes to be published in real time, imbuing Smallwood’s subversive wit with urgency and defiance. His 1851 memoir is prescient on the United States' tormented entanglement with race.

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THOMAS SMALLWOOD (1801-1883) was born into slavery near Washington, D.C., purchased his freedom, educated himself and became a shoemaker in the nation's capital. In the early 1840s, he organized an underground railroad operation that freed more than 200 people from slavery in the Washington-Baltimore region, while writing satirical newspaper dispatches about the escapes under a pseudonym. In his newspaper pieces, he gave the underground railroad its name. When the local police caught on, Smallwood made his own daring escape to Toronto, Canada, where he started a business manufacturing saws and published a short memoir in 1851. He never returned to the United States.

SCOTT SHANE was a newspaper reporter for 21 years at The Baltimore Sun and 15 years at The New York Times, where he shared two Pulitzer Prizes. He is the author of Flee North: A Forgotten Hero and the Fight for Freedom in Slavery's Borderland, the first book on Thomas Smallwood. His other books are Dismantling Utopia, an eyewitness account of the fall of the Soviet Union, and Objective Troy, about an American terrorist killed in a drone strike ordered by President Obama. He lives in Baltimore.