Even Bacon felt moved by Hubbard’s plea—“I felt very badly myself”— but he knew what would come next: Hubbard had to be whipped. So Bacon was astonished when Jefferson turned to him and said, “Ah, sir, we can’t punish him. He has suffered enough already.” Jefferson offered some counsel to Hubbard, “gave him a heap of good advice,” and sent him back to the nailery, where Reuben Grady was waiting, “expecting ...to whip him.”
Jefferson’s magnanimity seemed to spark a conversion in Hubbard. When he got to the nailery, he told Grady he’d been seeking religion for a long time, “but I never heard anything before that sounded so, or made me feel so, as I did when master said, ‘Go, and don’t do so any more.’ ” So now he was “determined to seek religion till I find it.” Bacon said, “Sure enough, he afterwards came to me for a permit to go and be baptized.” But that, too, was deception. On his authorized absences from the plantation to attend church, Hubbard made arrangements for another escape.
During the holiday season in late 1810, Hubbard vanished again. Documents about Hubbard’s escape reveal that Jefferson’s plantations were riven with secret networks. Jefferson had at least one spy in the slave community willing to inform on fellow slaves for cash; Jefferson wrote that he “engaged a trusty negro man of my own, and promised him a reward...if he could inform us so that [Hubbard] should be taken.” But the spy could not get anyone to talk. Jefferson wrote that Hubbard “has not been heard of.” But that was not true: a few people had heard of Hubbard’s movements.
Jefferson could not crack the wall of silence at Monticello, but an informer at Poplar Forest told the overseer that a boatman belonging to Colonel Randolph aided Hubbard’s escape, clandestinely ferrying him up the James River from Poplar Forest to the area around Monticello, even though white patrollers of two or three counties were hunting the fugitive. The boatman might have been part of a network that plied the Rivanna and James rivers, smuggling goods and fugitives.
Possibly, Hubbard tried to make contact with friends around Monticello; possibly, he was planning to flee to the North again; possibly, it was all disinformation planted by Hubbard’s friends. At some point Hubbard headed southwest, not north, across the Blue Ridge. He made his way to the town of Lexington, where he was able to live for over a year as a free man, being in possession of an impeccable manumission document.
His description appeared in the Richmond Enquirer: “a Nailor by trade, of 27 years of age, about six feet high, stout limbs and strong made, of daring demeanor, bold and harsh features, dark complexion, apt to drink freely and had even furnished himself with money and probably a free pass; on a former elopement he attempted to get out of the State Northwardly . . . and probably may have taken the same direction now.”
A year after his escape Hubbard was spotted in Lexington. Before he could be captured, he took off again, heading farther west into the Allegheny Mountains, but Jefferson put a slave tracker on his trail. Cornered and clapped in irons, Hubbard was brought back to Monticello, where Jefferson made an example of him: “I had him severely flogged in the presence of his old companions, and committed to jail.” Under the lash Hubbard revealed the details of his escape and the name of an accomplice; he had been able to elude capture by carrying genuine manumission papers he’d bought from a free black man in Albemarle County. The man who provided Hubbard with the papers spent six months in jail. Jefferson sold Hubbard to one of his overseers, and his final fate is not known.
Slaves lived as if in an occupied country. As Hubbard discovered, few could outrun the newspaper ads, slave patrols, vigilant sheriffs demanding papers and slave-catching bounty hunters with their guns and dogs. Hubbard was brave or desperate enough to try it twice, unmoved by the incentives Jefferson held out to cooperative, diligent, industrious slaves.
In 1817, Jefferson’s old friend, the Revolutionary War hero Thaddeus Kosciuszko, died in Switzerland. The Polish nobleman, who had arrived from Europe in 1776 to aid the Americans, left a substantial fortune to Jefferson. Kosciuszko bequeathed funds to free Jefferson’s slaves and purchase land and farming equipment for them to begin a life on their own. In the spring of 1819, Jefferson pondered what to do with the legacy. Kosciuszko had made him executor of the will, so Jefferson had a legal duty, as well as a personal obligation to his deceased friend, to carry out the terms of the document.
The terms came as no surprise to Jefferson. He had helped Kosciuszko draft the will, which states, “I hereby authorize my friend, Thomas Jefferson, to employ the whole [bequest] in purchasing Negroes from his own or any others and giving them liberty in my name.” Kosciuszko’s estate was nearly $20,000, the equivalent today of roughly $280,000. But Jefferson refused the gift, even though it would have reduced the debt hanging over Monticello, while also relieving him, in part at least, of what he himself had described in 1814 as the “moral reproach” of slavery.