Webb was born in Northampton County on the Eastern Shore of Virginia around 1682. Her mother, Ann Williams, was an English indentured servant. The origins of her enslaved father, Daniel Webb, are unknown. The Eastern Shore contained about 8 percent of Virginia’s population before the American Revolution and was home to the state’s largest population of free Blacks. Slavery was central to the region’s culture and economy, as about one in five households owned enslaved people. As elsewhere in early British America, free, indentured, and enslaved people of African, English, and Indigenous descent labored and lived together in the region’s small farmsteads. Webb was born in such a mixed household.
Because of her mixed-race parentage and out-of-wedlock birth, Webb, in accordance with English law, was bound into service for the first eighteen years of her life. During her youth, Webb likely performed domestic labor, cooking, dairying, laundering, and sewing for the household, and worked alongside male laborers in planting, cultivating, and tending tobacco.
Some of the most enduring lessons of Webb’s early years, however, were about law rather than labor. The Black community on the Eastern Shore was legally astute, and its members were active in protecting their rights to freedom, to property, and to sue in the local county courts. The most legally active were men who owned property, like Anthony Johnson (ca. 1600–1670), a Black man who was born enslaved, earned his freedom, purchased land, and established a farm on the Eastern Shore. Webb would have observed, however, that Black women also pursued their interests at the bar. From the diversity of legal remedies sought by the Eastern Shore’s Black community, Webb learned the importance of using the law to preserve rights to freedom. She also learned that slavery was not always a permanent, heritable status that denied legal personhood. For instance, two enslaved men in her household were freed during her youth, and while her father was enslaved, he witnessed at least one will and had a surname, attributes typically associated with freedom. At the same time, Webb would have been aware that the meaning of freedom was changing for free Blacks. Legal knowledge was crucial to navigating the shifting borderlines between slavery and freedom.
Webb was freed from service around 1700. She remained on the Eastern Shore, likely laboring in much the same way that she had as a bound servant. In 1703, she married an enslaved man named Left. Such unions not uncommon; free women of color outnumbered free men of color by almost two to one on the Eastern Shore, and laws in British America did not prohibit marriage between enslaved people and free people of color. Such marriages were often formalized through the efforts of wives, who insisted that their unions be given express mention in legal documents to protect their own freedom and that of any children born into the marriage, since the status of the child followed that of the mother.
To establish the legality of her marriage, Webb entered into a contract with Thomas Savage, Left’s enslaver. This was a legally astute decision on Webb’s part, but it required considerable sacrifice. According to Webb, she indentured herself to Savage for seven years, and she agreed that any children born into the marriage through 1711 would serve Savage until they were eighteen years old. After 1711, Left would be freed, and any children born to the couple thereafter would bear no obligation to Savage. Webb’s motive seems clear: she traded her labor—her only asset—in order to marry, to ensure the legal legitimacy of her progeny, and to keep her family free and intact. At the time, such arrangements often were tolerated by local legal institutions and enslavers because they kept free Black women from establishing independent households and prevented the birth of illegitimate children that might be a charge to the community. Such arrangements also benefited middling enslavers like Savage, providing them with access to labor in the form of indentured children.
Contrasting Views of Marriage in the Eighteenth Century
The contract not only established the legality of the Webb marriage, it also created a distinct relationship between Webb and the law. At the time, the legal doctrine of coverture brought married women under the legal persona of their husbands and stripped them of most of their legal rights. But because Left was enslaved and had no personhood under the law, Webb was the legal head of the household. Marriages such as Webb and Left’s resulted in female-headed households and lineages, with the children taking their mother’s surname, which existed in tension with the patriarchal model of the time.
Webb and Left had seven children: Dinah, born in 1704; Daniel, born in 1706; Frances, born in 1708; Ann, born sometime around 1711; Elizabeth, born in 1713; Elisha, born in 1716; and Abimelech, born in 1720. On April 17, 1711, the three oldest Webb children were bound to Savage as per the terms of their agreement. Savage, however, refused to free Left. And in June of 1716, Ann and Elizabeth also were bound to Savage, at his request. When Dinah turned eighteen in 1722, reaching the end of her term of indenture, Savage refused to free her.
Webb turned to the courts for legal remedy, petitioning the Northampton County Court on August 16, 1722, to release Dinah, as well as Daniel and Frances, from their indenture, asking that her taxed free Black women and increased the length of indenture for children born into unions such as Webb and Left’s to thirty or thirty-one years—nearly a lifetime in early Virginia. Already, Webb noted, the courts had extended the term of her children’s indenture from eighteen to twenty-one years based on revised laws, and she had reason to fear that their terms could be extended further. She bluntly asked the court if it was “Intending to Enslave [the] petitioner’s children.”Webb had good reason to fear for the freedom of her children. Laws were being passed in Virginia that increasingly limited the freedom of free Blacks and discouraged female-headed free Black families, linking them to political instability and conspiracies between free and enslaved Blacks. In 1722, laws were passed excluding free Blacks from voting and holding elected office; eventually they would be restricted from serving on juries. Laws that went into effect in 1723
Savage delayed the case until January 1723, when the court dismissed Webb’s petition, calling it “frivolous.” Courts often backed enslavers in such cases, reflecting a societal preference for keeping children in their households instead of allowing the formation of free Black households. Dinah would be released from servitude in 1725 when she turned twenty-one and sued Savage herself.
By 1725, Webb was the head of her own household, which included her youngest children, Elisha and Abimelech. In February 1725, Savage petitioned the court to have Lisha and Abimelech returned to his household and indentured to him. He argued that because Webb had no means to support her children, “who may be induced to take ill courses,” he had theto them.
Having seen the courts consistently back Savage’s attempts to indenture her children born after 1711 despite their agreement, Webb turned to chancery court, the court of last resort. On March 11, 1725, she sued Savage for failing to fulfill the terms of their contract. The contract itself had gone missing—Webb claimed that Savage had taken it—and a copy had never been entered into court records. For his part, Savage disputed Webb’s description of the contract, claiming that he had never agreed to free Left and that all of the Webb children were to serve him. He produced two witnesses who swore they had seen the contract and that Webb “agreed to serve seven years & that her children born in the lifetime of her husband Left should serve” Savage. Again, the court backed Savage, and on July 12, 1726, ordered Lisha and Abimelech Webb bound to him.
The following day, Webb was back in court after two people heard her declare that “if all Virginia negros had as good a heart as she had, they would all be free.” The Northampton County justices found these to beDisorderly speech such Webb’s was a small avenue of resistance for women in fractious, insular societies like the early Eastern Shore of Virginia. But this was no idle gossip. Webb’s words were politically charged, a calculated demonstration of her own racial consciousness and a deliberate threat of collective resistance. The justices ordered Webb to be stripped to the waist and given ten lashes “well laid on” at the whipping post outside of the courthouse.
Webb produced a free Black witness to attest to her version of the contract. Existing law rejected the testimony of enslaved people but did not yet explicitly prevent free Blacks from being witnesses. The justices, although apparently divided on the matter, ruled in April 1727 that Virginia law debarred legal testimony from free Blacks. Without witnesses to back her case, Webb declined to appear in the next court session. On July 11, 1727, Webb v. Savage was dismissed. As a result, Left remained enslaved for the rest of his life, and all the Webb children served Savage or his heirs into their early adulthood. Webb died in Northampton County around November 1764 and was buried at Hungars Parish Church.
Jane Webb’s Legacy
Although Webb ultimately failed to hold Savage to the terms of their contract, she did succeed in providing a meaningful lesson in legal resourcefulness to her children that was instrumental in maintaining their freedom. When her youngest daughter, Elisha, was sold illegally into slavery in Portsmouth, New Hampshire, in the 1740s, she utilized networks in New Hampshire and Virginia to gain her freedom. She even called on her mother’s assistance. Jane Webb helped obtain statements from witnesses, had them certified by the court, and sent them up north so that Elisha could regain her freedom. Webb’s eldest children, Dinah Webb Manly and Daniel Webb, migrated to North Carolina in the 1730s, which at the time was less hostile to free Blacks, and formed families and communities where some of their descendants still live today.
Webb’s life provides a window into the difficulties faced by free Black women who sought to maintain the freedom of their families in early Virginia. Her story also shows the power of the law and of local officials to shape the lives of free African American women. Yet against great odds, women like Webb persisted both in maintaining their families’ freedom and in transmitting their legal legacies to their descendants.