Part I

Part II

Part III

Part IV

Part V



(Map designed by C.K. Hickey. Text written by Gary A. Harki | The Virginian-Pilot)

The men bound Robert Irving’s hands with rope.

They pulled it taut, stretching his tall, lean body. His naked back was exposed.

A man stood behind him with a cowhide lash.

Whipping slaves in 1854 was a routine job.

Robert heard the crack, then felt leather dig into flesh. A moment’s pause, and the lash came again.

The reason for Robert’s punishment is lost to history. It could have been anything.

But as bad as the whipping was, there was worse to come.

It was November, and soon the slave jails in Norfolk would be filling up with men, women and children to be sold at the start of the new year. Slaves were one of the area’s top exports.

At 27, Robert was in his prime – bright and healthy. The widow who owned him knew he was worth a lot on the open market, more than $500 (that’s $18,000 in today’s money).

Somehow, he learned that she planned to sell him.

Robert thought of escape. The Underground Railroad thrived despite vicious efforts to stamp it out.

But someone bound him to Portsmouth in a way his owner never could.

Julia Irving's master, Gen. John Hodges, owned this house on North Street in Portsmouth. (Thé N. Pham | The Virginian-Pilot)

Julia Irving lived in a stately white house at the corner of North and Middle streets, the favorite of the elderly general and his wife who owned her.

Robert had loved Julia since he was a teenager. She was pretty despite the large scars on her head, reminders of some brutality.

Nine years earlier, the general had married them in his front parlor.

They weren’t allowed to live together, but Robert stayed a few blocks away at the naval hospital where he worked. They had three sons, many friends, a respected place in their community.

Robert faced a terrible choice and didn’t have much time. He could wait to be sold and torn from his family, or tear himself from them.

Escape meant entering a world of spies and slave hunters, missionaries and mercenaries. Few details of that world remain – the railroad’s survival depended on secrecy and subterfuge – but the path to freedom cut right through Hampton Roads.

The harbor here was a beacon for men like Robert. Those men would spend the rest of their lives reflecting on what they gained and what was lost.

Norfolk and Portsmouth in the early 1850s. On the Portsmouth side of the Elizabeth River, right, stands the United States Naval Hospital in the foreground, where Robert Irving lived and worked as a slave. (Courtesy of the Mariners' Museum, Newport News)

In 1854, Portsmouth was a town of about 8,500 people, nearly a quarter of them enslaved. In Norfolk, nearly a third of the city’s 14,000 residents were slaves, with a small population of free blacks.

Portsmouth sat on just over a half-square-mile, from North Street and what is now Olde Towne to the Gosport Navy Yard, and from the wharf back about eight blocks. A train ran down High Street to the docks.

Norfolk was crowded around the wharf on an anvil-shaped peninsula on the opposite side of the Elizabeth River. It was framed on the west by Smith’s Creek, near what is now the Hague, and to the east by the marshy Newtons Creek a few blocks past Church Street. In total, it covered about a mile. Congested downtown streets eventually widened and gave way to farmland.

Together, the communities had the largest port in Virginia, bringing in goods from Philadelphia, Baltimore and New York while exporting cotton, wheat and tobacco.

With that port came a collection of sailors – rogues, world travelers and pirates. Along Crawford and Water streets in Portsmouth, prostitutes peered out of saloons with names like “The Globe.” Traders haggled with merchants.

Anxious travelers to the north waited for their always tardy ships, and locals traveled back and forth across the Elizabeth on a graffiti-marred ferry crewed by slaves.

Everywhere, slaves moved among the whites, deferring to their masters by day and at night, gathering privately in kitchens and anywhere else they could with families and friends.

Sometimes, the talk turned to escape.


Around the turn of the 19th century, the system of routes and safe houses known today as the Underground Railroad began to take shape.

Written accounts have survived that document the escapes of about 100 slaves from Portsmouth and Norfolk, but no one connected to the railroad was foolish enough to keep a complete log. The exact number who fled will never be known.

Slaveholders grew more enraged and paranoid with each passing year.

“There is no doubt but that secret agencies are in our midst for the purpose of offering inducements to our slaves to make their escape North,” an April 1854 editorial from the Southern Argus in Norfolk reads. “Slaves are allowed far too much liberty by their masters. We ourselves can plead guilty of the charge; but this is a time when we may awake and repent.”

Slave laws had been more relaxed at the turn of the 19th century, but by 1854, they had tightened. Slaves couldn’t have black preachers in their churches for fear they would incite rebellion. They had to carry papers from their owners giving them permission to be out on the streets.

There was a small industry built around “Negro Repositories” – in essence, private jails – to more securely house slaves awaiting auction and to capture and punish those who tried to escape.

As Robert Irving struggled over whether to flee, he would have known the risks, as well as the stories of those who’d successfully traveled along the railroad.

Already, two fugitives from Hampton Roads had drawn national attention, becoming lightning rods for abolitionists and slaveholders across the country.


George Latimer was born in Norfolk on the Fourth of July. By 1842, he was 23 years old and had passed through a succession of owners. Twice, he was thrown into prison because of an owner’s debts. He wound up in the hands of James Gray, an ill-tempered storekeeper and sawmill owner who was quick to punch, kick and whip him.

Latimer decided to escape with his pregnant wife, Rebecca.

After several failed attempts, they finally stowed away aboard a steamer. They hid in a compartment next to the boilers – it was dark and excruciatingly hot, and through cracks in the partition, they could see the ship’s barroom, with men who would have gladly turned them in for a bounty.

Latimer arrived in Boston days later and was soon spotted by an acquaintance of Gray. He was captured, and his wife had to stay hidden.

The slave owner came to take him back. Gray told police that Latimer had stolen from his store. That was enough to get Latimer thrown in jail, giving Gray time to start the extradition process.

But the arrest stirred passionate abolitionists in Boston and nearby New Bedford. They met several times in late October and early November, trying to figure out how to prevent Latimer from being sent back.

Among the speakers at the rallies was Frederick Douglass, who had escaped Maryland less than five years before.

The abolitionists started two petitions, one requesting that the state legislature ban public officials or public property from being used to detain or arrest escaped slaves and another demanding that a law be passed severing any connection between Massachusetts and slavery.

(Massachusetts Historical Society)

Gray eventually agreed to sell Latimer after the sheriff told him he would no longer hold fugitive slaves. Latimer’s supporters bought his freedom for $400, and he was cleared of the theft charges.

Back in Norfolk, a committee formed to discuss how to respond to “the Boston outrage.”

In Massachusetts, the petitions continued to circulate, getting more than 100,000 signatures.

(Massachusetts Historical Society)

The following year, the Massachusetts legislature passed the “Latimer statute,” which forbade state officials from helping capture fugitive slaves.

The law antagonized the South and helped lead Congress to pass the Fugitive Slave Act.

Part of a set of bills known as the Compromise of 1850, it essentially forced free states to aid in the capture of runaways.

Among the bill’s supporters was Massachusetts Sen. Daniel Webster. Abolitionists in his state attacked him immediately for the betrayal.

“The word liberty in the mouth of Mr. Webster sounds like the word love in the mouth of a courtesan,” wrote Ralph Waldo Emerson.

Massachusetts abolitionists, enraged by the law, now wanted to test it in the courts. So did Southern slaveholders.

Both sides would soon find a test subject, though the end result was something neither expected.

Shadrach Minkins

Passed by Congress in 1850, the Fugitive Slave Act required that all escaped slaves were, upon capture, to be returned to their masters and that officials and citizens of free states must cooperate.

Shadrach Minkins had escaped Norfolk and was working as a waiter in Boston when Congress passed the Fugitive Slave Act.

His owner, John DeBree, hired Norfolk constable John Caphart to go north and find him.

Caphart, a man of nearly 60, ran a private slave jail and specialized in tracking down fugitives. He earned 50 cents a head for whippings.

Harriet Beecher Stowe drew on descriptions of Caphart to create some of the characters in “Uncle Tom’s Cabin,” which would be published two years later and spur the abolitionist cause.

Caphart’s search brought him to Boston, where abolitionists quickly made a poster warning citizens to be wary.

“His face is rather short for a man so long, rather square shaped; an uncommonly hard, bad face and ugly … a face which seems made for a slave hunter,” it read.

Caphart tracked Minkins to the Cornhill Coffee House, where he worked, and got a warrant for his arrest on Feb. 14, 1851.

The next morning, Minkins was quietly arrested at work and taken the short distance to the courthouse.

Deputy Marshal John Riley knew that word of Minkins’ arrest would spread fast. He alerted the mayor that there was likely to be trouble.

Then he returned to the courthouse and barred all but the front doors. Guards were placed, but people were still allowed in.

Within a half-hour, a crowd of about 200 – many free blacks and some whites – filled the courtroom.

A reporter said the protesters looked “as if they were about to spring over the rail and tear the prisoner away.”

Abolitionist lawyers huddled to mount Minkins’ defense.

By the time the hearing started, about an hour after the arrest, a mob of seething abolitionists stood outside.

Minkins’ situation appeared hopeless. The Fugitive Slave Act barred him from testifying or having his case heard by a jury. The hearing was a formality to make sure the papers for his return were in order.

Nevertheless, Minkins’ lawyers managed to postpone it for three days.

Police started clearing the courtroom.

A man approached Minkins.

Don’t be afraid, he said. We’ll stand by you.

But Minkins, who had started the day a free man and now faced enslavement and certain punishment, was terrified.

He stripped off his coat and loosened his kerchief.

“If I die, I die like a man,” he said.

Minkins and his lawyers remained in the courtroom after everyone else had left.

Outside, on Court House Square, the crowd stood fast. Someone suggested they could easily free Minkins if they rushed the courthouse.

People began to pound on the doors.

Marshals tried to hold them shut, but more than 15 men burst inside.

They carried Minkins, according to one account, “as they would a child in their arms.” He was taken through the streets to an attic on Beacon Hill.

After the rescue, Minkins was kept hidden and safe by abolitionists and free blacks, including George Latimer. He was paid to keep an eye on Minkins’ owner, who’d come to Boston.

John DeBree’s journey was for naught.

The slave hunters returned to Norfolk empty-handed.

An illustration of fugitive slaves escaping from the Eastern Shore of Maryland.

In Virginia, the successful escapes and the spectacle of Northerners thumbing their nose at the new law hardened slaveholders’ determination, but there was little they could do.

Many whites in Norfolk and Portsmouth, including Robert Irving’s owner, “hired out” their slaves – allowing them to work for someone else in exchange for passing most of their earnings to the owner. Slaves laid bricks, worked at sawmills, caulked ships and handled cargo.

Slave owners were trapped between their desire to keep valuable property secure and the need to allow slaves enough freedom to get to work in the shops and businesses huddled near the docks.

The tension bred resentment aimed at Northern abolitionists and the slaves themselves.

“The ancestors of these Unde’ground people stole away the long-teethed Cannibals of Africa and sold them to the Southern planter and now … they want to steal them away from the planter and carry them Northwardly,” fumed an editorial in the Richmond Daily Dispatch. “So it’s all the time stealing.”

The fear that a slave might escape sometimes led owners to sell them south.

For Robert, his recent whipping was nothing compared to the punishment he’d receive if caught trying to escape.

Even if he succeeded, he’d be leaving his wife and children in a hostile town that would probably punish them for his flight.

But there was reason to hope. Whole families had been known to reunite once free, and the notorious escapes from the rough docks gave Robert cause for optimism.

Precisely how and when he made his decision isn’t known.

The only thing that can be said with certainty is that one day, Robert Irving walked away.



(Library of Congress)

In 1848, Henry Brown’s pregnant wife and children were sold away, and he was left alone in Richmond.

The skilled tobacco worker decided he’d had enough of slavery and was determined to make his escape.

He hatched a plan with a friend in his church choir, a free black man named James Ceasar Anthony Smith, and a shoemaker and gambler named Samuel Alexander Smith.

They decided that Brown’s best hope for escape was by rail, in a wooden box 2½ feet deep by 2 feet wide.

On March 23, 1849, Brown crawled into the box. The other two men sealed it and marked “dry goods” on the side.

Brown traveled from Richmond to Aquia Creek, north of Fredericksburg.

There, he was transferred to a steamboat, where the box was set on its end. Brown was turned on his head for several hours as the boat made its way up the Potomac River to Washington.

“I felt my eyes swelling as if they would burst from their sockets; and the veins on my temples were dreadfully distended with pressure of blood upon my head,” he later said.

Eventually, two men tipped the box over and had a seat. Brown, relieved, suffered quietly beneath them.

He arrived in Philadelphia early on March 24 and was taken to the office of the Pennsylvania Anti-Slavery Society.

When the box was opened, Brown popped out, exhausted, but little worse for wear after 26 hours.

His escape was a well-publicized early tale from the Underground Railroad, tipping off slave hunters to the inventive method.

Samuel Smith tried to ship another slave that year, but he was arrested and sentenced to six and a half years in prison.

James Smith also was arrested, but he escaped conviction and joined Brown in Philadelphia by the end of the year.

Brown became a singer and magician, using the name H. “Box” Brown, and eventually took his act to England.

He continued to use his original box for years, crawling out of it during performances.

About the series

This story was recounted in narrative form using a range of sources. Cassandra Newby-Alexander, a professor of history and director of the Joseph Jenkins Roberts Center for the Study of the African Diaspora at Norfolk State University, deserves special thanks for doing much of the research that serves as the backbone of this tale. She also was interviewed for the series, as were Robert B. Hitchings, former head archivist and historian, Sargeant Memorial Collection, Norfolk Public Library; Troy Valos, a researcher at the Sargeant Memorial Collection; Delores Freeman, visitor services specialist at the Great Dismal Swamp National Wildlife Refuge and Bill Barker, archivist at The Mariners’ Museum.

Books and manuscripts

The American Beacon newspaper, “Bound for Canaan: The story of the Underground Railroad,” by Fergus Bordewich; “People of the Underground Railroad: A Biographical Dictionary,” by Tom Calarco; “The Shores of Freedom: The Maritime Underground Railroad in North Carolina, 1800-1861,” by David Cecelski; “The Two Autobiographical Fragments of George W. Latimer,” by Asa J. Davis; “Slavery’s Exiles: The Story of the American Maroons,” by Sylviane Diouf; “The Dismal Swamp,” Harper’s Magazine, Sept. 13, 1856; “Historical and Descriptive Sketches of Norfolk and Vicinity, Including Portsmouth and the Adjacent Counties,” by William S. Forrest; “History of New Bedford, Massachusetts,” by Thomas Garrett and Leonard Ellis; “Flight and Rebellion: Slave Resistance in 18th Century Virginia,” by Gerald Mullin; The Norfolk and Portsmouth Herald newspaper; The Norfolk Southern Argus newspaper; African Methodist Society (Emanuel AME) application to National Park Service National Underground Railroad Network to Freedom by Cassandra Newby-Alexander; The Portsmouth Globe newspaper; The Portsmouth Star newspaper; “The Underground Railroad,” by Wilbur Siebert; “The African society becomes Emanuel African Methodist Episcopal church, Portsmouth, Virginia: One hundred and seventy-two long years,” by Charles E. Stewart; “Fugitive Slave in the Gold Rush: Life and Adventures of James Williams,” by James Williams; “God Made Man, Man Made the Slave: The Autobiography of George Teamoh,” by F.N. Boney, Richard L. Huma and Rafia Zafar; “The Fugitive’s Gibraltar,” by Kathryn Grover; “Shadrach Minkins: From Fugitive Slave to Citizen,” by Gary Collison; “Station Master on the Underground Railroad: The Life and Letters of Thomas Garrett,” by James A. McGowan; “Voices From Within the Veil,” by William H. Alexander, Cassandra Newby-Alexander and Charles H. Ford; “History of Portsmouth, Virginia,” by Dean Burgess and Mildred Holladay;

“Old-Time Advertising Cuts and Typography,” edited by Stephen O. Saxe; “Handbook of Early Advertising Art” by Clarence Hornung; “Historical Research Paper: The Naval Hospital Near Norfolk” by Wilhelm H. Solheim III; “Oral History Project: African American Historical Society of Portsmouth”; “Norfolk State University Historical Look at Lincolnsville; The First Black Community in Portsmouth, Virginia” by B. Nathaniel Smith; “The History of Norfolk, Virginia” by Harrison W. Burton; “The Great Dismal: A Swamp Memoir” by Bland Simpson; “Ghosts of Virginia’s Tidewater” by L.B. Taylor Jr.; “Free Blacks in Norfolk, Virginia 1790- 1800: The Darker Side of Freedom” by Tommy L. Bogger; Massachusetts court records; The Richmond Times Dispatch newspaper.


“Scraps of African Methodist Episcopal History: Electronic Edition., 1826-1911” by James Handy; The Library of Virginia Life Histories Collection; Narratives from the Federal Writers’ Project, 1936-1938, Library of Congress (audio and written); "Race Time Place" by Cassandra Newby-Alexander

“Blobbybirdman’s Peregrinations” by Mark Robinson; Wikipedia; Mike’s Black History; "Chronicling America" by the Library of Congress.

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