The Dark Side of Thomas Jefferson

A new portrait of the founding father challenges the long-held perception of Thomas Jefferson as a benevolent slaveholder

(Illustration by Charis Tsevis)
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Flogging to this degree does not persuade someone to work; it disables him. But it also sends a message to the other slaves, especially those, like Jimmy, who belonged to the elite class of Hemings servants and might think they were above the authority of Gabriel Lilly. Once he recovered, Jimmy Hemings fled Monticello, joining the community of free blacks and runaways who made a living as boatmen on the James River, floating up and down between Richmond and obscure backwater villages. Contacting Hemings through Oldham, Jefferson tried to persuade him to come home, but did not set the slave catchers after him. There is no record that Jefferson made any remonstrance against Lilly, who was unrepentant about the beating and loss of a valuable slave; indeed, he demanded that his salary be doubled to £100. This put Jefferson in a quandary. He displayed no misgivings about the regime that Oldham characterized as “the most cruel,” but £100 was more than he wanted to pay. Jefferson wrote that Lilly as an overseer “is as good a one as can be”—“certainly I can never get a man who fulfills my purposes better than he does.”

On a recent afternoon at Monticello, Fraser Neiman, the head archaeologist, led the way down the mountain into a ravine, following the trace of a road laid out by Jefferson for his carriage rides. It passed the house of Edmund Bacon, the overseer Jefferson employed from 1806 to 1822, about a mile from the mansion. When Jefferson retired from the presidency in 1809, he moved the nailery from the summit—he no longer wanted even to see it, let alone manage it—to a site downhill 100 yards from Bacon’s house. The archaeologists discovered unmistakable evidence of the shop—nails, nail rod, charcoal, coal and slag. Neiman pointed out on his map locations of the shop and Bacon’s house. “The nailery was a socially fractious place,” he said. “One suspects that’s part of the reason for getting it off the mountaintop and putting it right here next to the overseer’s house.”

About 600 feet east of Bacon’s house stood the cabin of James Hubbard, a slave who lived by himself. The archaeologists dug more than 100 test pits at this site but came up with nothing; still, when they brought in metal detectors and turned up a few wrought nails, it was enough evidence to convince them that they had found the actual site of Hubbard’s house. Hubbard was 11 years old and living with his family at Poplar Forest, Jefferson’s second plantation, near Lynchburg, Virginia, in 1794, when Jefferson brought him to Monticello to work in the new nailery on the mountaintop. His assignment was a sign of Jefferson’s favor for the Hubbard family. James’ father, a skilled shoemaker, had risen to the post of foreman of labor at Poplar Forest; Jefferson saw similar potential in the son. At first James performed abysmally, wasting more material than any of the other nail boys. Perhaps he was just a slow learner; perhaps he hated it; but he made himself better and better at the miserable work, swinging his hammer thousands of times a day, until he excelled. When Jefferson measured the nailery’s output he found that Hubbard had reached the top—90 percent efficiency—in converting nail rod to finished nails.

A model slave, eager to improve himself, Hubbard grasped every opportunity the system offered. In his time off from the nailery, he took on additional tasks to earn cash. He sacrificed sleep to make money by burning charcoal, tending a kiln through the night. Jefferson also paid him for hauling—a position of trust because a man with a horse and permission to leave the plantation could easily escape. Through his industriousness Hubbard laid aside enough cash to purchase some fine clothes, including a hat, knee breeches and two overcoats.

Then one day in the summer of 1805, early in Jefferson’s second term as president, Hubbard vanished. For years he had patiently carried out an elaborate deception, pretending to be the loyal, hardworking slave. He had done that hard work not to soften a life in slavery but to escape it. The clothing was not for show; it was a disguise.

Hubbard had been gone for many weeks when the president received a letter from the sheriff of Fairfax County. He had in custody a man named Hubbard who had confessed to being an escaped slave. In his confession Hubbard revealed the details of his escape. He had made a deal with Wilson Lilly, son of the overseer Gabriel Lilly, paying him $5 and an overcoat in exchange for false emancipation documents and a travel pass to Washington. But illiteracy was Hubbard’s downfall: He did not realize that the documents Wilson Lilly had written were not very persuasive. When Hubbard reached Fairfax County, about 100 miles north of Monticello, the sheriff stopped him, demanding to see his papers. The sheriff, who knew forgeries when he saw them and arrested Hubbard, also asked Jefferson for a reward because he had run “a great Risk” arresting “as large a fellow as he is.”

Hubbard was returned to Monticello. If he received some punishment for his escape, there is no record of it. In fact, it seems that Hubbard was forgiven and regained Jefferson’s trust within a year. The October 1806 schedule of work for the nailery shows Hubbard working with the heaviest gauge of rod with a daily output of 15 pounds of nails. That Christmas, Jefferson allowed him to travel from Monticello to Poplar Forest to see his family. Jefferson may have trusted him again, but Bacon remained wary.

One day when Bacon was trying to fill an order for nails, he found that the entire stock of eight-penny nails—300 pounds of nails worth $50—was gone: “Of course they had been stolen.” He immediately suspected James Hubbard and confronted him, but Hubbard “denied it powerfully.” Bacon ransacked Hubbard’s cabin and “every place I could think of” but came up empty-handed. Despite the lack of evidence, Bacon remained convinced of Hubbard’s guilt. He conferred with the white manager of the nailery, Reuben Grady: “Let us drop it. He has hid them somewhere, and if we say no more about it, we shall find them.”

Walking through the woods after a heavy rain, Bacon spotted muddy tracks on the leaves on one side of the path. He followed the tracks to their end, where he found the nails buried in a large box. Immediately, he went up the mountain to inform Jefferson of the discovery and of his certainty that Hubbard was the thief. Jefferson was “very much surprised and felt very badly about it” because Hubbard “had always been a favorite servant.” Jefferson said he would question Hubbard personally the next morning when he went on his usual ride past Bacon’s house.

When Jefferson showed up the next day, Bacon had Hubbard called in. At the sight of his master, Hubbard burst into tears. Bacon wrote, “I never saw any person, white or black, feel as badly as he did when he saw his master. He was mortified and distressed beyond measure....[W]e all had confidence in him. Now his character was gone.” Hubbard tearfully begged Jefferson’s pardon “over and over again.” For a slave, burglary was a capital crime. A runaway slave who once broke into Bacon’s private storehouse and stole three pieces of bacon and a bag of cornmeal was condemned to hang in Albemarle County. The governor commuted his sentence, and the slave was “transported,” the legal term for being sold by the state to the Deep South or West Indies.


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