Interior of the engine house during John Brown's raid on Harpers Ferry
Frank Leslie's illustrated newspaper, v. 8, no. 205 (1859 Nov. 5), p. 359 (Wikimedia Commons)Intereior

Editor's note: For those who are wondering about the retro title of this black-history series, please take a moment to learn about historian Joel A. Rogers, author of the 1934 book 100 Amazing Facts About the Negro With Complete Proof, to whom these "amazing facts" are an homage.

Amazing Fact About the Negro No. 60: Who were the black people killed in the raid on Harpers Ferry?

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Can you imagine the headline if proslavery forces had had their own cable-network news ticker during John Brown’s infamous raid on the arsenal at Harpers Ferry, Va., launched on Oct. 16, 1859? “BREAKING NEWS: First victim of abolitionist terror plot in Virginia a free black man. Story developing.” Could this have been true? 

Turns out, it was true, and it was fatal.

Yet in contemporary memory, the magnitude of John Brown’s radical abolitionist persona and his white body “a-mouldering in the grave,” and what his righteous cause to start an armed slave revolt portended for a nation about to be torn in two by slavery overwhelmed the fate of his raid’s more minor characters. Those seeking the full story should pick up Tony Horwitz’s vivid 2011 account, Midnight Rising: John Brown and the Raid That Sparked the Civil War.  In this column, we follow just one rifle spark to the first man shot—in the back.

The Man Who Wasn’t There 

But first, any discussion of free black men at Harpers Ferry should begin with the most important one who wasn’t there: Frederick Douglass.  Douglass and Brown had met in Springfield, Mass., a decade before. Though they couldn’t have looked more different, Douglass, Brown and their closest compatriots shared “black hearts,” the title of my colleague John Stauffer’s moving first book about interracial alliances and the eventual fallout from John Brown’s raid.

In Douglass’ own words in his newspaper, the North Star, on Feb. 11, 1848, Brown was:

“[T]hough a white gentleman … in sympathy, a black man, and … as deeply interested in our cause, as though his own soul had been pierced by the iron of slavery. After shaking my hand with a grip peculiar to Anti-Slavery men, Mr. Brown said that for many years he had been standing by the great sea of American bondmen, and anxiously watching for some true men to rise above its dark level, possessing the energy of head and heart to demand freedom for their whole people, and congratulated myself and the cause, that he now saw much men rising in all directions, the result of which, he knew, must be the downfall of slavery. Mr. Brown is one of the most earnest and interesting men that I have met in a long time.”

Weeks before Brown was to launch his own raid of liberation, however, Douglass balked at joining him during a rendezvous at a quarry in Southern Pennsylvania. “ ‘I want you for a special purpose,’ ” Douglass recalled Brown saying in his 1881 memoir, The Life and Times of Frederick Douglass (1892 ed.). “ ‘When I strike the bees will begin to swarm, and I shall want you to help hive them.’ ” Brown’s reason for striking Harpers Ferry: It was home to one of the most productive federal arsenals in the country. The catch: Douglass thought Brown’s plot was implausible, at best, or as he put it: “I looked at him with some astonishment, that he could rest upon a reed so weak and broken, and told him that Virginia would blow him and his hostages sky-high, rather than that he should hold Harpers Ferry an hour.”

Douglass’ refusal was a grave disappointment to Brown. As novelist James McBride has his narrator, Henrietta (nickname “Onion”), say in The Good Lord Bird, winner of this year’s National Book Award, Brown’s “great heartbreak was his friend Mr. Douglass,” even though Henrietta “[k]nowed from the first, really, that there weren’t no way Mr. Douglass could’a brung hisself to fight a real war. He was a speeching parlor man.”

In the aftermath, Douglass still drew suspicion for his suspected complicity in the planning of the raid. Investigators found a letter from Douglass in Brown’s possession, and though it was two years old and silent on Harpers Ferry, the governor of Virginia enlisted the support of the Buchanan administration to track him down on charges of “murder, robbery, and inciting servile insurrection,” as quoted in John Stauffer’s dual biography of Douglass and Lincoln, Giants: The Parallel Lives of Frederick Douglass and Abraham Lincoln. Before fleeing to Canada, then on to England for a pre-planned tour, as he wrote, defensively, in the New York Daily Tribune on Nov. 4, 1859, Douglass had his son “hide or destroy incriminating documents” at home. It wasn’t until the following June, in 1860, that Virginia’s governor “dropped the charges against him,” Stauffer writes. 

For a time, he had been “the most wanted man in America.” (Interestingly, Douglass visited Harpers Ferry in 1881 to deliver a speech on Brown at Storer College and donated the proceeds from the printed version to a fund for a John Brown Professorship. In it, he shared the above recollections and declared, “When John Brown stretched forth his arm the sky was cleared. The time for compromises was gone.”)

RIP Heyward Shepherd

While abolitionists like Douglass were sympathetic to Brown’s ultimate goal, they were skeptical of the mission itself, and so, despite financial support, on the eve of the raid, Brown had only been able to assemble a force of 22, including himself and five black men. (More on them later.)

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As Brown and his men moved into Harpers Ferry (less than 70 miles west of Baltimore and Washington, D.C.) on the night of Oct. 16, 1859, the people of the town had no clue what was about to happen. Here’s where brother Heyward Shepherd came in.

Shepherd was a baggage master working the overnight shift at the train depot in Harpers Ferry, when he must have heard the B&O express train out of Wheeling, Va., slowing down on the Potomac Bridge—about to be ambushed by a group of Brown’s raiders, including Brown’s son, Oliver. The train’s white conductor, Andrew Phelps, stepped out with four others to see what was going on. Once inside the covered portion of the railroad bridge, Phelps spotted the raiders’ rifle ends. Then, suddenly, one of his men had his lantern snuffed out after Phelps heard a shout, “Stand and deliver!”

The next thing Phelps knew, “a tall black man staggered out from the covered bridge, crying, ‘I am shot,’ ” as Horwitz writes. It was Shepherd, whose own version of the events was later transmitted to a U.S. Senate Select Committee on the Harper’s Ferry Invasion (1860) by his attending physician at the railroad office, John D. Starry. In his testimony, Starry said:

“When I got there I found the negro porter, Hayward, shot, the ball entering from behind, through the body, nearly on a line with the base of the heart, a little below it. He told me that he had been out on the railroad bridge looking for a watchman who was missing, and he had been ordered to halt by some men who were there, and, instead of doing that, he turned to go back to the office, and as he turned they shot him in the back. I understood from him that he walked from there to the office, and when I found him he was lying on a plank upon two chairs in the office … He was a free negro, and had permission of the county court to remain in Jefferson county … I saw him about daylight; he was still living. I understood he died between twelve and one o’clock on Monday, the next day.”

So it was, Horwitz writes, noting the irony, that “John Brown’s campaign to liberate slaves had claimed as its first casualty a free black man, shot down while defying the orders of armed whites.” My own elementary school history teacher, James McHenry, in a classroom about two hours’ drive from Harpers Ferry, enthusiastically pointed out to our fifth-grade class the same irony, almost as a sign from God of what he gleefully characterized as Brown’s lunacy. I remember feeling very bad for the brother, and I felt bad for John Brown as well.

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In the dark, no one could ever be sure who had shot Shepherd, Horwitz adds, but just “[h]ours after,” one of Brown’s men, Steward Taylor, was discovered “by the bridge, pale and trembling [saying] he had shot a man and believed he had killed him.” Taylor was right about that at least.

In One Hundred Amazing Facts About the Negro With Complete Proof (No. 52), our old friend Joel A. Rogers claims Shepherd was shot “while running off to arouse the white people.” However, if Shepherd ever spoke of his motives for running, they were not recorded, and anyway, at the time he was shot, it was still too early for anyone in the town to know they were being attacked as an insurrection to end slavery. In fact, Horwitz explains, John Brown himself told Conductor Phelps he had no intention of shooting anyone on the railroad, or in the town (he blamed the Shepherd incident on “bad management,” Horwitz explains). 

What Brown did want were the arsenal’s store of weapons and for word to spread to the slaves in the region that the day of emancipation—indeed, Armageddon—was at hand. To this end, Brown even allowed Phelps’ train to continue on its way to Baltimore in hopes the message would get out to the city’s large free black population, whom he expected to rally to his side at Harpers Ferry, along with slaves who Brown imagined would flee their plantations in the immediate vicinity, and become his black army. That decision backfired: Instead, the conductor’s cable messages made it up the chain to the War Department and ultimately to President James Buchanan, who ordered in the Marines under Col. Robert E. Lee. The rest, as they say, is history.

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Sadly, we know little more about Shepherd’s life before the raid, other than that he was reportedly married, had several children and owned property in the area. Joseph Barry, author of the 1903 book, The Strange Story of Harpers Ferry, put Shepherd at 44 and said he was “very black” and “uncommonly tall.” (Recall from one of our earlier columns, family and employment were two major reasons many freed slaves, despite the danger of reenslavement, refused to leave the South before the Civil War, as in the case of three sets of my own fourth-great grandparents, who lived near Harpers Ferry.)

What we do know is that Shepherd had the backing of his white employer and sponsor at the depot, Fontaine Beckham, who also happened to be the mayor. Though a slaveowner, Beckham apparently had helped another free black man purchase his family out of bondage. According to one contemporary in the town, “ ‘The old man [Beckham] had had him [Shepherd] ten or twelve years, and liked him very much’ ” (proof, Horwitz points out, of “the murky and insecure status of ‘free’ blacks in Virginia, who, like Shepherd, needed white patrons to vouch for them in order to stay”). Obviously, Beckham felt something for Shepherd. When he learned of his death, Beckham apparently ran out with his gun for revenge, only to be gunned down himself “on the railroad trestle,” Horwitz writes, “a site so exposed that no one was able to recover his body.” By then, all hell had broken loose.

Brown’s Black Men

Another aspect of the tragic shooting of Heyward Shepherd at Harpers Ferry is that long before then, John Brown had embraced working with black men on unusually equal terms. Besides his friendship with Frederick Douglass, Brown had chosen to live near the free black community of Timbucto (no kidding!) in the Adirondack mountains of New York. (For more, see Stephen Oates’ To Purge This Land With Blood: A Biography of John Brown.) It is not surprising then, that while Brown didn’t know Heyward Shepherd from Adam, he had recruited five black men to join his raid, four free and one a fugitive slave. Among the free men was John A. Copeland, a 23-year-old Oberlin College student once imprisoned for helping to rescue the runaway slave John Price. A second free man was Copeland’s uncle, Lewis S. Leary, a harness maker also from Oberlin whose wife eventually had a grandson we know as the poet Langston Hughes. When Copeland saw Leary shot during the raid, he apparently hid in rocks down by the river, only to be discovered by a group of white men who would have lynched him had John Starry, the doctor who had tended to Heyward Shepherd, not intervened and had Copeland jailed instead.

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The third free black man—and the one whose situation was most tragic—in John Brown’s army was Dangerfield Newby. His decision to join Brown’s raiders was as personal as it can get. At 48, Newby was the oldest of Brown’s recruits, the son of a former slave and her master. By then he was on a mission to rescue his own wife and seven children, who were being held in slavery about 53 miles from Harpers Ferry in Brentsville, Va. (according to Philip J. Schwartz in Migrants Against Slavery: Virginians and the Nation. In fact, Newby was carrying with him a letter his wife had written to him, imploring him to liberate her and their children, as Philip Schwarz writes in “Dangerfield Newby,” from the African American National Biography. It is unclear what happened to Newby’s enslaved family members after he was killed at Harpers Ferry.

The fourth black man in Brown’s raid was Shields Green (aka “Emperor”). He was a fugitive slave who had left his son in South Carolina en route to Canada, then back to the U.S., where he was present at that historic war council between Frederick Douglass and John Brown. Unlike Douglass, Green chose to fight and paid for it with his execution alongside Copeland and two others on Dec. 16, 1859, according to Zoe Trodd in “Shields Green,” from the African American National Biography.

The last of Brown’s free black men was Osborne P. Anderson, the son of a free black father and white mother who had moved from Pennsylvania to Canada for fear of being kidnapped by slave catchers following the Fugitive Slave Act of 1850. There, Anderson attended the Chatham Conference in 1858, a secret constitutional convention to organize a government for the revolutionary black state that John Brown intended to form in Southern Appalachia. Anderson was the sole survivor from Brown’s main raiding party at Harpers Ferry, and once he made it back to Canada, he wrote his account of the raid, A Voice From Harper’s Ferry, according to Steven Niven in “Osborne Perry Anderson,” from the African American National Biography.

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In addition to these men, and Shepherd, three slaves lost their lives during or after the Harpers Ferry Raid, according to Horwitz: one, a coachman Jim (Washington), by drowning; a second, Ben (Allstadt), in Charlestown prison; and the third, his mother, Ary, who had tended to him. 

In every way, tactically, the raid was a failure. In all, 17 raiders were captured or killed, including 13 whites (Brown, plus his two sons, Oliver and Watson, among them) and four blacks (not counting Ary), while Brown and his men killed five, four white men plus Shepherd (nine others were wounded), according to the Senate Select Committee Report.

John Brown was captured, tried, found guilty of treason and executed by hanging in Charles Town, Va., (now West Virginia) on Dec. 2, 1859. His legend only grew, however, and by the time the Civil War erupted in 1861, his name lived on in song. Today, his is one of the most recognized names of the period. Even Quentin Tarantino has fantasized about making a film about him, though this time with a different ending.

Faithful Slave?

While we continue to know little about the life of Heyward Shepherd, his memory remains trapped on the bridge between fact and legend, progress and nostalgia, Paul A. Shackel explains in his fascinating 2003 article in Historical Archaeology, “Heyward Shepherd: The Faithful Slave Memorial.”

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Jumping ahead, in 1895, the first memorial installed at the site of the raid in Harpers Ferry commemorated John Brown. For blacks and many white Northerners, he was a martyred hero—to Southerners, their worst nightmare, a white man bearing arms to liberate black slaves.

A decade later, the United Daughters of the Confederacy proposed a starkly different kind of memorial—to the “Faithful Slave”—in order teach future generations “ ‘that the white men of the South were the negro’s best friend’ ” (as quoted by Shackel). By 1920, the UDC concentrated the effort on honoring Heyward Shepherd, who, according to Mary McKinney, president-general of the UDC, had “ ‘held too dear the lives of ‘Ole Massa’ and ‘Ole Miss’us’ to fulfill Brown’s order of rapine and murder.’ ” McKinney must have forgotten that Shepherd was free, and not a slave on Ole Massa’s plantation when he died.

On Oct. 10, 1931, the monument to Shepherd was dedicated, after Harpers Ferry agreed to provide the municipal space. According to Shackel, approximately 100 African Americans and 300 whites attended, with several of the speeches explicitly defending slavery. In response, a headline in the Afro Newspaper described the event as “Unveiling Uncle Tom” and the “Anti John Brown.” Even though neither side could claim to know much about the real Shepherd, in the political struggle unfolding it was critical to men like Walter White of the NAACP to decry the monument’s dedication as an “ ‘attempt to destroy the truth and perpetuate a story that Negroes did not participate of their own free will in the struggle for their emancipation’ ” (as quoted by Shackel).

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By the time the civil rights movement took off in the 1950s, the National Park Service took over the land surrounding the Shepherd monument at Harpers Ferry, and during its renovation of the site in the late 1970s, the monument was put into storage. It did not reappear until 1981, yet even then, there were threats that the monument would be defaced, so the entire thing was boxed in plywood. 

At the same time, there was intense debate swirling in Washington over the monument’s inscription, which in part read: “To Heyward Shepherd, exemplifying the character and faithfulness of thousands of negroes who under many temptations throughout subsequent years of war, so conducted themselves that no stain was left upon a record which is the peculiar heritage of the American People, and an everlasting tribute to the best in both races.” While groups like the UDC wanted the monument displayed as is, organizations like the NAACP argued for providing accompanying context. 

Eventually, the plywood was taken off in 1995, and new interpretive material was added, including a brief panel with a poem in tribute to John Brown by W. E. B. Du Bois. Again, the UDC charged political correctness, while the NAACP insisted, “We don’t think that the Daughters of the Confederacy and the Sons of the Confederacy had that much love for Negroes.” One NAACP representative even suggested dropping the monument into the Potomac River.

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In The Good Lord Bird, James McBride has his own fascinating take. In fact, he takes what little we have and weaves it together in such a way as to give Heyward Shepherd a more prominent role on both sides of the track, so to speak. He even gives Shepherd a nickname: “the Rail Man.” In this at times uproarious telling, Shepherd stands to profit from Brown’s Raid—and would have, had he been given the right password at the bridge. I’ll let you read the novel to find out how. As with most events in history, the truth is almost always more complicated than any news ticker you see scrolling by.

As always, you can find more "Amazing Facts About the Negro" on The Root, and check back each week as we count to 100.

Henry Louis Gates Jr. is the Alphonse Fletcher University Professor and the director of the W.E.B. Du Bois Institute for African and African-American Research at Harvard University. He is also the editor-in-chief of The Root. Follow him on Twitter and Facebook.

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