With the slavery debate raging, Thomas Smallwood, a free Black shoemaker living in the 19th-century borderlands between the North and South, had a mission: free as many enslaved people as possible and rub their former enslavers’ faces in his success. In an 1842 dispatch to a New York newspaper, he noted that a slaveholder’s “walking property walked off.”

In “Flee North: A Forgotten Hero and the Fight for Freedom in Slavery’s Borderland,” former New York Times correspondent Scott Shane chronicles the remarkable story of how Smallwood led enslaved people out of bondage and became the documented source of the term “underground railroad.”

“It was your cruelty to him that made him disappear by that same ‘under ground rail-road’ or steam balloon,” Smallwood said in an Aug. 10, 1842, letter, referring to a complaining police officer’s characterization of the escape method he used to lead slaves from Virginia, Maryland and D.C. to freedom.

With his white companion Charles Torrey, a graduate of Exeter and Yale, Smallwood operated in the then-small town of the District of Columbia and the then-booming metropolis of Baltimore. They spirited as many as 400 slaves to freedom between 1844 and 1846, Shane told me.

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Smallwood appears to have been a little-noticed figure in the annals of pre-Civil War U.S. history, but, as Shane documents, was part of the pantheon of Blacks whose audacity, cunning and resourcefulness left a jagged scar in the image of slavery as it was practiced in this region of the U.S. during the early to mid-19th century.

Smallwood’s name and exploits should be considered along with those of Robert Smalls, who sneaked a Confederate gunboat out of a South Carolina harbor during the Civil War and handed it over to Union forces, and Edward Tarr, an iron worker and the first free Black landowner west of the Blue Ridge mountains, who acquired land that today is part of Interstate 81 in Virginia. Scholars have recorded the kind of daring that was displayed by Africans enslaved in the Americas and the boldness and determination many exhibited in the ways they attempted to gain their freedom.

In the case of Smallwood, he didn’t wait for slaves to approach him as they sought their freedom, Shane said. Smallwood actively recruited runaways, and instead of leading them from safe house to safe house through the woods at night, the way Harriet Tubman did, Smallwood and Torrey secreted slaves in wagons, leading them from D.C. to safe houses in Baltimore. From there, he would take them north with a goal of ending up in Canada.

“Flee North” is set in the region where the North and South blended into D.C., which, at the time, was little more than a sleepy town of about 40,000 people. Baltimore, on the other hand, already had a population of more than 100,000. Baltimore was a city bustling with commerce, second only to New York City as an epicenter of the Eastern Seaboard trading ports. As it turns out, Baltimore was also a jumping-off point for getting slaves away from slavers, Shane wrote.

“Flee North” by Scott Shane is an account of the life of extraordinary abolitionist, liberator and writer Thomas Smallwood.

Smallwood’s letters to an abolitionist newspaper in Albany, New York, were part of his campaign to put an elbow into the ribs of white slaveholders and slave traders. Smallwood, Shane said, was intentional in the ways he prodded those who “thought of themselves as vastly superior” to Blacks.

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“He was truly remarkable, a real self-made man,” Shane said. Smallwood bought his freedom for $500 at the Prince George’s County Courthouse in 1832, developing a shoemaking business and living in a frame house on Fourth Street southeast, near the Navy Yard, Shane said.

Shane also told me the shoemaker who freed enslaved people and documented his success wanted to let the slaveholders know that their property was gone for good. In letters to the New York paper, he identified the runaways, bragging to their enslavers. He used their names in his articles and even named some of the fleeing slaves. That touch was his way of striking back against the racism that underlies slavery, Shane said.

Shane said he was captivated by Smallwood’s wit, capping a boldness that fought the local slavers, the slave traders — especially Hope Slatter, the region’s leading merchant in human chattel — and the local police, whose primary job was to enforce the Fugitive Slave Act of 1793.

In addition, Shane told me, the letters were a way of getting back at people who were pampered, sheltered beneficiaries of the system of chattel slavery.

Shane spoke to me about how he came to this topic after time spent as a foreign correspondent in Russia in the 1980s and 1990s. It was a time when Russians were coming to terms with how communism had reshaped Russian culture and history.

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Shane said the history of slavery and the “underground railroad” Smallwood led in the Baltimore-Washington region was even more compelling.

Scott Shane was a reporter for 15 years at The New York Times, where he was twice a member of teams that won Pulitzer Prizes. Before that, he spent 21 years at The Baltimore Sun. (Francie Weeks)

At the time, tobacco plantations were waning but cotton was booming and needed the free labor of slavery, Shane said.

“The story has three characters: Smallwood, Torrey and Slatter. Each of them is fascinating.”

He said Slatter thrived on Pratt Street, operating a slave prison in which he stashed the people his operatives snared for shipment to the New Orleans, Louisiana, slave markets. The book documents three shipments south by Slatter of 307 humans between September 1843 and April 1844. He died rich, his Mobile, Alabama, gravesite adorned by a “big, white block of a tomb.”

Torrey’s style was similar to abolitionist John Brown, with whom he associated and was arrested for what Shane described as a “brazen escape attempt” of two brothers. Torrey died in prison.

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Smallwood died anonymously in 1883 in Toronto, Ontario, having fled to Canada when pursuit of him was heating up.

" I know he attended Colored Conventions there, but there are no photographs. No statues, either. There ought to be at least a plaque.”

Ronald A. Taylor is a Washington, D.C., native and veteran journalist who has written and reported for The Washington Post, Atlanta Constitution, Black Issues in Higher Education and Bloomberg BNA. He grew up near the Washington Navy Yard.

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