How An Ex-Slave and His White Abolitionist-Sidekick Rescued Slaves, Taunted Slavers, and Gave The “Underground Railroad” Its Name

And we continue with our American stories. Our next story comes to us from Pulitzer Prize-winning author and journalist Scott Shane. Shane is the author of Flee North: Forgotten Hero in the Fight for Freedom in Slavery’s Borderland. Let’s take a listen.

The central character of my book is a guy named Thomas Smallwood, and I just want to take you to what he was up to in 1842. He’s a man who had been born in slavery, had basically educated himself, built a business as a shoemaker, and he was living about a 15-minute walk from the United States Capitol in Southeast Washington. By day, he’s running this shoemaking business to support his family. He has a wife and four kids, and a fifth kid on the way. At night, he’s organizing these mass escapes by the wagonload.

And even as he’s doing all this during the day and at night, he somehow is finding time to write up a new dispatch for an abolitionist newspaper in Albany, New York, which used the real names of the slaveholders and the real names of the people escaping from them, and basically were based on the satirical style of Charles Dickens, and he wrote them using a pseudonym from Charles Dickens, because everything he was doing was illegal and he was in danger of arrest at any moment. And what he wrote was the only real-time, first-hand accounts of escapes from slavery ever published. They were so much in real time that sometimes, he writes, he had held a particular dispatch for a week or two to make sure the people he’s writing about had made it to safety in upstate New York or Canada. So, this is Thomas Smallwood. His own experience of slavery had been relatively benign. It happened that he was inherited, along with his sister, by a woman who then made a second marriage to a man by the name of John Ferguson, who was a minister and somewhat anti-slavery, certainly somewhat embarrassed to find himself as a slaveholder. But he was encumbered by the terms of a will, so he could only buy Smallwood and his sister essentially from his new wife and her children. And he did that, and he said Smallwood, when small was 15, that he would give him his freedom at the age of 30, but he would have to pay him back over time. So, John Ferguson and his wife, the slaveholder, taught Smallwood to read, which was quite unusual at the time. And Smallwood talks about how he impressed the neighbors by being able to spell as a young boy words of two syllables like baker and cider,” he says.

And later, he worked for another guy as a household servant for an educator by the name of John Macleod in Washington. And this guy was apparently quite a fervent educator, and he had adult children of a similar mindset, and all of them helped kind of guide Thomas in his reading and encourage him. And so, by the time he had completed the purchase of his freedom and he was a free man at the age of 30, he was extremely well-educated. He’d read widely in contemporary literature, in ancient literacy, ancient philosophy. He knew an awful lot. So, at that time, he’s married, he’s building his shoemaking business, and he gets involved in something called the Colonization Movement. Colonization was the idea that African Americans should start a new life in some other country, that, basically, their prospects here were dim and they would do better to go elsewhere. Usually, it was Liberia in West Africa, which was a new country founded by the American Colonization Society, and for a while Smallwood was quite intrigued by this possibility, but then he had a change of heart because he realized that, in fact, a lot of slaveholders were behind the Colonization Society, and one of their key goals was to get Black people, particularly free Black people, out of the United States, so it was really more of an ethnic cleansing operation. Boldemot was the largest free Black community in the country, and free Blacks significantly outnumbered slave Blacks in the cities, in Washington and Baltimore, so he turned against that movement, but he was still extremely pained and angry about slavery, not so much about his own experience, but about much of what he had witnessed and wanted to do something about it. And just about that time, this guy Torrey comes from New England and moves to Washington, theoretically to become a newspaper correspondent for little abolitionist papers across the North, and the two of them get together because Smallwood has heard that Torrey was arrested in Annapolis, Maryland, the capitol, after going there to try to write about a convention of slaveholders, and they spot him and figure out that he’s not on their side, and a mob gathers, and anyway, he’s taken to jail, more or less for his own safety. But this all gets written up in the paper and Smallwood reads about it, and he thinks, “Who is this crazy white man who was confronting the slaveholders, you know, essentially on their own turf? I want to meet this guy.” And it happened that Smallwood’s wife, Elizabeth, did the laundry for the boarding house in D.C. where Torrey was living. So he asks his wife, “Can you introduce me to this guy Torrey?” And she sets up a meeting. And it’s so interesting to me to think about this. This is in January of 1842. These two guys, so Smallwood’s about 40, Torrey is about 28, and they’re kind of opposites in many ways. They meet across their generation of part; they meet across the course, the chasm of race. Torrey’s grandfather, who raised him after his parents died of tuberculosis, had been, had served in Congress as quite a prominent family. He’d gone to Exeter and Yale. Smallwood, born in slavery, totally self-educated, never went to school a day in his life. So, they’re so different, and yet by the time the two of them meet, they both seem equally dedicated to the cause of doing something to combat slavery, but also a little bit tired of talking about it. They want to do something practical, and so as they talk, they come up with this scheme to start helping them escape. And there are several things that they’re doing that are a little bit unusual. They want to do it not by ones and twos, but by the wagonload. So they start packing wagons with 10 to 15, even 20 men, women, and children, covering it over as discuss in some way, and they’ll take off in the middle of the night and head north. They also, at the beginning, were recruiting people to escape. They weren’t waiting for people to say, “Hey, I’d kind of like to escape, do you know anyone who can help me?” They would actually — Smallwood would actually approach people and say, you know, “We got a wagonload going, and you want to be aboard?” And the third thing would be that they had a larger strategy in mind, and that was to demoralize the slaveholders.

And you’re listening to Pulitzer Prize-winning author and journalist Scott Shane tell the story of an unlikely collaboration between a former slave, Thomas Smallwood, and a white man interested in freeing slaves, too, named Charles Torrey, and how the two together went to try and free not just one or two slaves at a time, but slaves by the wagonload, a revolutionary idea at the time, and doing it overground, not underground, even going so far as to recruit those slaves or escape. The story of Thomas Smallwood and his partner in crime (as it was a crime then to do these things), Charles Torrey. Their story continues here on our American Stories.

Our American Stories. Born into slavery, by the 1840s, Thomas Smallwood was free and self-educated. He recruited a young white abolitionist named Charles Torrey, and together these two set out to do something practical to combat slavery. That was to, one, recruit slaves; and two, arrange for their escape by the wagonload; and three, demoralize the slaveholders themselves. Here again is Scott Shane.

The idea was, if we essentially make off with these people’s wealth, because their human property was extremely valuable at the time, they’ll just realize that the idea of enslaving people is not going to work, and they’ll change their ways and they’ll start hiring workers instead of enslaving them.
And they had some success at that.
Smallwood talks about overhearing some people whose, as he puts it, “human property,” walked off, and he overhears them saying, “I’m never going to buy another slave,” and that was sort of a sensible decision in those circumstances.
I calculated roughly.
I was looking at a particular wagonload that Smallwood describes in some detail, and I made a rough estimate that the value of the 15 people on this wagon on the slave market at the time would have been something like $200,000 in today’s dollars. So, you’re talking about a fairly good-sized bank robbery every time a wagonload goes north, and you’re talking about people losing a large share of their wealth. So, their dream was that you would undermine slavery, sort of slaveholder by slaveholder, and you would also be doing it in this splashy way. You know, if you have 15 people leaving in a wagon, they come from several households, so a number of slaveholders are going to wake up in the morning and say, “Where is everybody?” And this would get a lot of attention. And they’re in Washington, D.C. They’re in the Capitol, and some of the people whose slaves they are helping to escape are members of Congress, members of the Cabinet, other public employees who have brought their enslaved workers from somewhere else and brought them to Washington. So, they thought that would have a particular resonance, and so that, too, sort of set their operation apart. So, as part of my story, I looked at a third character in addition to Thomas Smallwood and Charles Torrey, the third guy that I looked at was Hope Slatter. And there pass, these three men’s, passed cross in various ways, and Hope Slatter was the leading slave trader in the region from the late 1830s to the late 1840s. So, these guys are, in a strange sense, they’re almost competitors, so they’re really enemies. One of the things that was quite interesting about Hope Slatter, though, was in addition to the drive to make money, which he made a whole lot of in his 10 years or so in Baltimore buying and selling human beings, he also wanted respect that would match with his wealth.
But he didn’t get it, it seems that.
The slaveholders, even though they’re quite dependent on and did business with the slave traders, needed somebody to look down on, and a lot of them chose to look down on the slave traders. So he was constantly trying to curry favor with the sort of powers about town and about the state of Maryland. At one point he actually loans his big fancy carriage for the day to the visiting President of the United States, James Polk, and Polk uses Slatter’s carriage, and it’s written up in the paper. So, Slatter’s always on the lookout for ways to become respectable, so to speak. At one point, they’re building a big new Methodist church, and one of the ways they’re raising money for it is they’re selling the pews. In other words, you pay a big chunk of money and that’s going to be your family pew forever. So, Slatter buys a pew in this church, but once again he’s frustrated because the family who’s bought the pew behind his, the man announces they’re not going to ever attend that church as long as Slatter and his family are attending, because he doesn’t want to look at this guy while worshiping. So, Slatter does not find the respectability that he is seeking, and eventually he retires, essentially, from the slave trade in Baltimore and moves far to the south, finds people who can give him the respect that he’s been seeking all these years. Once I learned that Thomas Smallwood had written these dispatches to the Albany paper, which was originally called Tocsin of Liberty, which is an old word for “bell,” so essentially “Liberty Bell.” I checked in the Library of Congress and found that the largest run of that newspaper still in existence appeared to be in the Boston Public Library. Unfortunately, they were shut down in 2020 during the pandemic. But eventually I got through to some people and they took up my cause, and eventually they dug these out of warehouse and put them on microfilm, and I went to the library and downloaded them all onto a thumb drive and spent several months reading Smallwood’s dispatches. So, I’m reading along at one point and I find him addressing a slaveholder by real name and talking about how perhaps his enslaved workers got away by that Underground Railroad or steam balloon that one of your city constables was worrying.
About the other day. And I think that’s kind of funny.
He’s talking about Underground Railroad, but in a way that it sounds like it’s not in common parlance. Anyway, he elaborates later in another dispatch on that story, and he names the constable, and essentially this is a fairly notorious police constable in Baltimore and Washington who made a lot of money as a slave catcher. Anyway, this guy was understandably frustrated that large numbers of people were escaping and he could not figure out where they were going, and so apparently, in some kind of outburst of frustration, he said, “They must be leaving by Underground Railroad or steam balloon.” Those were sort of non-existent technologies. There were railroads, but there were no Underground Railroads. So, it was essentially like somebody might say, “They must have been teleported to another state. They must have been abducted by aliens.” In other words, I have no idea where they’re going. And Smallwood heard about this and ends up loving it because it’s a compliment to him, to his escape operation, the people who are making the escapes. So he starts using this phrase Underground Railroad and just sort of builds a world around it in his imagination. He starts advising the slaveholders in his dispatches to report to the office of the Underground Railroad in Washington to inquire about their lost property. He appoints himself general agent of all the branches of the National Underground Railroad. He at one point talks about how he can’t reveal the secret of the Underground Railroad, which is known only to the President and his Cabinet. And so he’s just having a good old time using the Underground Railroad, this mythical transport system, as a way to beat up on the slaveholders and make fun of them and their slave-catching police allies. So, you know, I’m reading this stuff and wondering, you know, it sounds like this is the origin of the use of that phrase and that concept. Could that be? And I start poking around. It turns out there are some old stories about where that term comes from, but they don’t hold up to much scrutiny, and most scholars had rejected them as folklore. And then I went into the big 19th-century newspaper databases that have been built up over the last 20 years. The ones I mainly use were Newspapers.com and GenealogyBank.com, and I just plugged in that phrase, and sure enough, all of the early uses of Underground Railroad were from Smallwood’s dispatches and other articles. His white sidekick, Charles Torrey, becomes editor of that paper, so Smallwood is sending the dispatches to Torrey, and Torrey begins to use the term Underground Railroad in his articles for the paper. But that’s where it all seems to start. And within a couple of years, it sort of lost its origin as a joke and as a way of mocking the slaveholders, and it’s just become a way of describing escapes, a sort of generic term for escapes from slavery, especially those using help along the way. So now I can say with confidence that that is actually the solution to that historical mystery, and Thomas Smallwood is the guy who gave the Underground Railroad.

its name. And a terrific job on the production, editing, and storytelling by our own Greg Hengler, and a special thanks to Pulitzer Prize-winning author and journalist Scott Shane. He’s the author of Flee North: A Forgotten Hero and the Fight for Freedom in Slavery’s Borderland. And we learn where that term Underground Railroad comes. There was nothing underground about it, but boy, was Smallwood and his paddle Charles Torrey trying to stick it to the slave owners, working together to end slavery in their own way. Their story here on our American Stories.