Kyle Chattleton: During the summer of 1805, a young man yearned for freedom. His name was James Hubbard, and for the first twenty-two years of his life he had been enslaved by Thomas Jefferson. Hubbard, like countless other African Americans, had been confined to a dehumanizing system of forced labor and oppression. But one day, armed with a disguise and forged legal papers, he sought to break the binds of slavery — James Hubbard was escaping the Monticello plantation.

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James Hubbard was the son of James and Cate Hubbard. He was born on the Monticello plantation in 1783. But a few years later, Thomas Jefferson relocated the Hubbard family to Poplar Forest, forcing them to move to a plantation ninety miles away.

The Hubbard family’s circumstances reflected how the thoughts and whims of their enslaver dictated their lives. From Jefferson’s perspective, Poplar Forest was a source of wealth and income. It was a tobacco plantation, and there James Hubbard’s father became a “head man,” responsible for supervising the work of fellow enslaved individuals on the plantation. Jefferson felt like Hubbard’s father was worthy of trust and authority, yet also viewed him and the rest of his family as moveable, economic pieces of property.

Because of this, James Hubbard found himself constantly being forced to move and, as a result, leave family and friends behind. When Hubbard was eleven years old, Jefferson had him moved back to the Monticello plantation. The rest of his family, however, stayed at Poplar Forest.

This all took place because Jefferson wanted Hubbard to make nails. Along Monticello’s Mulberry Row, Hubbard worked with other children in a nailery, turning long pieces of iron into smaller nails. This took place six days a week, from dawn until dusk, in a confined space next to hot forges. Jefferson recorded that, in any given day, the children could make up to ten thousand nails.

At first, Hubbard made less nails than others around him, but in time he became one of the most productive nailers on Mulberry Row. Jefferson would occasionally pay members of the enslaved community for their efforts. These kinds of incentives were not uncommon in the Upper South at this time, and many enslavers paid small amounts of money for work they deemed “above and beyond” the regularly tasked labor of those they enslaved. Perhaps this is why Hubbard not only perfected his nail-making skills, but also chose to work in his spare time making charcoal for Jefferson.

It appears that, as time went on, Hubbard carefully made plans to escape Jefferson and Monticello. With the money he earned from all that extra work, Hubbard acquired two significant items: a nice set of clothes as well as forged legal papers meant to show he was a free man. And in the late summer of 1805, Hubbard left the plantation and made his way toward the city of Washington.

It is not certain why Hubbard chose the capital of the United States, but he likely would have known about the African American community in the city; Edith Fossett and Ursula Hughes, two others enslaved by Jefferson, had worked in the White House, and made trips between Monticello and Washington during Jefferson’s presidency.

But Hubbard would not make it all the way to the capital. His attempt to escape from Monticello was also fundamentally an attempt to evade the racist ideas that were used to justify slavery. Because of the color of his skin, Hubbard was stopped by a jailer in Fairfax County and arrested on mere suspicion. Eventually, Hubbard confessed that he was attempting to escape Monticello, and was forcibly brought back to the plantation.

For enslaved African Americans at Monticello and throughout the rest of the country, escape could be met with severe consequences. Slavery was enforced through threats, violence, and family separation. Hubbard certainly would have been aware of this reality, which makes his actions all the more striking.

And yet, after being brought back to Monticello, Hubbard continued to focus on a world beyond the confines of slavery. Next to the fire and heat of nail-making and charcoal burning, Hubbard planned a second attempt. He would not escape during the summer like last time. Instead, he would try to leave during the winter when plantation work slowed down and his absence might not be as easily noticed.

Six years later at the age of twenty-seven, Hubbard escaped Monticello for the second time. An advertisement was put out a few months later. It stated:

“Ranaway, from his plantation […] a negro man called james hubbard […] about six feet high, stout limbs and strong made, of daring demeanor, bold and harsh features, dark complexion, […] and had even furnished himself with money and probably a free pass; […] whoever apprehends the said slave, and delivers him […] shall receive Forty Dollars in addition to what the law allows.”

Amid the winter cold Hubbard made his way west across the Blue Ridge Mountains, eventually settling in the Shenandoah Valley. It appears that Hubbard was able to live as a free man for at least a year. But while Hubbard was determined to stay free, Jefferson was persistent in his wish to re-enslave Hubbard. He received word that Hubbard was in the Shenandoah Valley, and paid someone seventy dollars to find and apprehend him.

Unfortunately, Hubbard was rediscovered, shackled, and brought back to Monticello. Additionally, Jefferson wished to communicate to the rest of the enslaved community that actions like Hubbard’s would not be tolerated. And so he had Hubbard punished. Jefferson wrote, “I had him severely flogged in the presence of his old companions, and committed to jail.” Jefferson ultimately sold Hubbard to Reuben Perry, but told Perry that “all circumstances convince me he will never again serve any man as a slave,” and therefore Hubbard should be sold out of Virginia. To this day, historians are not certain what happened to Hubbard after.

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James Hubbard knew that he deserved a better life, one in which he was treated with the dignity and respect that were his by right as a human being. His actions display a constant desire for that other life. Slavery in America was pervasive, held up by ideas about people based on race. The obstacles stacked against enslaved people must have seemed insurmountable, and Hubbard faced many. From literal fences around plantations, to the hundreds of miles he'd likely need to travel to get to a free state or to a place where he could live anonymously, facing scores of people along the way who believed in those false ideas about skin color and who would hinder his escape, and of course, to the punishments he would face if caught, Hubbard understood what resisting slavery could lead to. And yet he and millions of others forced into slavery persevered and resisted it in unique, commendable, and inspiring ways. Through their resistance, enslaved people affirmed their humanity time and again, eventually leading to the downfall of the system. Enslaved people made different choices: some ran, some complied, some fought. All were human beings, surviving an inhumane system as best they could. Hubbard decided that he would leave the plantation in hope, eager for a world beyond the confines of Monticello.