Winney Grimshaw

Portrait of William Henry Tayloe by Charles Bird King

Her parents were Esther Jackson and Bill Grimshaw, enslaved by William Henry Tayloe.[4] Both were valuable to Mount Airy, as Esther was a spinner, and Bill served as Tayloe's head carpenter from 1832 to 1845. Bill worked on the Octagon in Washington D.C., the Tayloe's winter residence and later the temporary home of President Madison and his family for six months after the British burned the White House.[4][5]  

Mount Airy did not keep birth records, but Winney Grimshaw is listed on the inventory for the Old House on January 1, 1827, recorded as being one year old.[4] Esther and Bill had seven children, Lizza (1824), Winney (1826), Anna (1827), Juliet (1829), James (1831), Charlotte (1834), and Henry (1837).[6]

In 1830, at four years old, Grimshaw was sent to Washington, D.C. to live with her grandmother and namesake, Winney Jackson, who worked as Anne Tayloe's chambermaid.[4][5] At age five, she returned to Mount Airy lived with her mother in the Old House, and her father lived a few miles away at the home quarter of Mount Airy.[4] Grimshaw did not have an assigned job until 1839, when she was thirteen years old. Most enslaved children had been working for a few years by this age.[4] Due to Esther's role as a spinner, she was often in proximity to the household where Grimshaw spent much of her childhood.

In 1840, at fourteen, Grimshaw was sent out to her first job accompanied by her sisters – Anna, twelve years old, and Juliet, ten years old. They were lent to Mrs. William N. Ward, the wife of a local clergyman. She was expected to feed, clothe, and house the girls. This was an easy way for masters to train young enslaved girls for the life of domestic service.[4]

Around 1841 or 1842, Winney returned to Mount Airy, living for the first time without the company of her family. She lived on a farming quarter with forty other slaves, though her job was to tend to Mrs. Monday, the sickly wife of her white master.[4] A year later in 1843, at seventeen years old, Winney Grimshaw was documented as a spinner, and in 1844 she married Jacob Carrington, who had worked in the plantation's gristmill since the age of nine.[4] Jacob Carrington's father was unusual in that he was an emancipated African American, though this did not benefit Jacob, as the law of partus sequitur ventrem ruled that the title of slavery was passed down maternally. Together Winney and Jacob lived in the home quarter, and in 1844 at eighteen years old, Grimshaw gave birth to her first son, John Carrington.[4]

In 1845, Bill Grimshaw ran away after being whipped as punishment for a disagreement with one of his white supervisors. He was the only Mount Airy slave to run away permanently in the years between 1808 and 1860.[4] As punishment and to discourage other runways, Tayloe broke up the Grimshaw family. Letters between Juliet and her older sister Lizza display the distress felt at the separation of their family.[4] At nineteen Grimshaw, her fourteen-year-old brother James, and her baby John, were all sent to the Oakland cotton plantation in Alabama.[4] Virginia became a large exporter of slave labor in the U.S. after the Act Prohibiting Importation of Slaves took effect in 1808.[7] William Henry Tayloe sent a total of 218 Mount Airy slaves to Alabama between 1833 and 1862.[4] Winney was a trained spinner and James was training as a carpenter, so their usefulness on a cotton plantation was minimal, but their transfer was an example for other Mount Airy slaves. Plantation labor was much more difficult than domestic labor which was seen as a more favorable position.[8] It is unknown the exact cause, but in 1847 during her time at the plantation Grimshaw's son, John Carrington, died.[4]

During this time in Grimshaw's life, she was faced with the exploitation of her white masters that many enslaved women endured throughout the Atlantic World before abolition.[9] (See for example the biographies of Alice Clifton, Jane the Runaway, Bridge Town, and Betty, George and Martha Washington's enslaved seamstress.) Scholars have found that many enslaved women's most intimate lives were closely managed and dictated by their owners.[10] With her husband remaining at Mount Airy, In 1849, Winney Grimshaw bore her supervisor Richard Donnahan's son, naming him John after her late infant.[4] Grimshaw is documented as his black mistress throughout his family correspondence.[4] In 1850, a second child was born, Julia, who died as a young baby. In 1853 Grimshaw gave birth to another baby girl Lizza.[4] Both babies shared namesakes with their aunts, Winney's sisters Juliet and Lizza, which demonstrates the importance of family ties even after being transferred to the plantation.

After the birth of Lizza, William Henry Tayloe attempted to break up the relationship between Grimshaw and Donnahan by first encouraging Donnahan to manage a different plantation that was miles away.[4] When this did not work, Tayloe focused on Grimshaw instead, giving her four-year-old son John as a New Year's gift to his niece, Lucy Tayloe, who documented the exchange with a "Thank You" letter.[4] This did not end the relationship between Donnahan and Grimshaw, and in 1855 Willie Anne was born, followed by William Henry.[4] Because Tayloe owned the reproductive rights of his slaves, any of Grimshaw's children would become his property. It was unusual that Tayloe disapproved of her children with Donnahan, as increasing slave ownership would increase prosperity.[10] The remainder of Grimshaw's children stayed with her, and in 1858 Tayloe dismissed Donnahan, separating the white supervisor from his slave.[4] In 1861, Grimshaw was documented as a housekeeper on the Larkin plantation for her overseer, John W. Ramey. In 1862, Grimshaw gave birth to another baby, Thorton, fathered by Ramey.[4] This created tensions between Mrs. Ramey and her husband, as well as Ramey and Tayloe. In November 1865 Grimshaw is listed again at the Larkin plantation with five children, suggesting that she had given birth to yet another baby.[4]

Shortly after the beginning of the Civil War, Tayloe moved many of his enslaved workers on Mount Airy to Alabama.[4] Many families that had been separated were given the chance to reunite, however, Grimshaw's husband, Jacob Carrington, had determined that freedom was more important than returning to his wife. He left Mount Airy in December 1861; Richard Dunn claims that he "deserted to the Yankee army" when he found out about Tayloe's plan to move.[4] Carrington's decision demonstrates the difficult choice that many enslaved women and men had to make between family and freedom, like that of Winney's father Bill.

Though the Grimshaw family is considered to be well-documented, other than the mention of the births of Winney Grimshaw's children, her documentation is sparse. She is listed as a domestic worker at the Oakland plantation between the ages of 19 and 28, then at the Woodlawn plantation between ages 29 and 32, and at Larkin plantation from ages 33 to 40.[4][6] All three plantations were located in Alabama and were owned by William Henry Tayloe. Winney Grimshaw's name appears for the last time at the Larkin plantation in 1866.[4] Tayloe, reflecting on his time as a slaveholder, mentions Winney's name for the last time in 1868 saying, "Winney Grimshaw could fill a volume with interesting events, if [she] could write."[4] Neither Grimshaw nor any of her children are listed on the 1870 US census.[11]