Dr. Pleasant Winston (1792-1876) was born in Henrico County, Virginia, and attended Jefferson Medical College. In 1820, Winston married Elizabeth Cheadle Clark (1800-1852), daughter of Bowling and Elizabeth Cheadle Clark; the couple would have five sons. Among Elizabeth Clark Winston's five siblings were Lucy Clark (1793-1864), Mary Harris Clark (1797-1865), and Bowling Clark (1798-1877), likely the recipients of most of the letters in this collection.

A member of the Society of Friends, Winston was opposed to slavery and moved his family to Indiana in 1830 to be distanced from it. The 1850 census lists the Winstons, with sons Ambrose, Charles, and William H. H., as residents of Franklin (Montgomery County), Indiana. Elizabeth Winston later returned to Virginia with sons Ambrose, Charles, and William H. H. and died there. Pleasant Winston remained in Indiana with eldest sons Bowling and Pleasant.

Ambrose Whitlock Winston was born in Indiana on May 30, 1835. Though he appears with his family in the 1850 federal census in Montgomery County, Indiana, he apparently moved to Virginia with his mother and two of his brothers later that year. A resident of Lynchubrg, Winston enlisted in Company E, 58th Virginia Infantry at Richmond on October 12, 1861. By March, 1862, he had been commissioned a lieutenant. He is listed on company muster rolls until May 1, 1862. (According to brother William H. H. Winston, Ambrose served throughout the war in southwestern Virginia, "with the exception of one year that he was detailed Quarter-Master-Sergeant to buy supplies around Lynchburg for the Army." He is likely the A. W. Winston who served in Company A, 22nd Virginia Cavalry, and was paroled at Campbell Court House, Virginia, on June 12, 1865. On May 20, 1863, Ambrose Winston married Lucy Eldridge Davis (1838-1864); later he married Lelia Lee Rucker (1848-1916), with whom he fathered four children. Ambrose W. Whitlock died on May 11, 1897, and was buried in Winston-Clark Family Cemetery, Altavista (Campbell County), Virginia.

William Henry Harrison Winston was born in Montgmery County, Indiana, on July 29, 1840. In early 1861, he was an overseer on the Campbell County, Virginia, plantation ("LaGrange") of his uncle, Bowling Clark. On May 23, 1861, with his brother Charles, Winston went to Manassas, Virginia, where they joined the Lynchburg Home Guard, which later became Company G, 11th Virginia Infantry. Winston remained with the regiment until being wounded at the Battle of Frazier's Farm (June 30, 1862). He rejoined the regiment following the Battle of Antietam. At the Battle of Gettysburg, he was again wounded and was taken prisoner, held at Fort McKinsie, then Fort Delaware, and finally Point Lookout before being exchanged on February 13, 1865. He married Nancy Powell Moorman (1841-1916) on February 29, 1866; the couple had three children. The 1870 census shows the Winstons living and farming in Amherst County, Virginia. William H. H. Winston died while living with his daughter in Southampton County, Virginia, on March 14, 1934, and was buried in Spring Hill Cemetery, Lynchburg, Virginia.

Charles Jones Winston was born in Montgomery County, Indiana, on August 22, 1837. In early 1861, he was overseer on Hills Creek plantation in Campbell County, Virginia. At the outbreak of the American Civil War, he enlisted with his brother William in the Lynchburg Home Guard, later Company G, 11th Virginia Infantry. He remained with the regiment throughout the war, but is listed on company muster rolls as sick on October 1, 1861; wounded in action, July 3, 1863; and again wounded in action April 1, 1865. In 1867, he married Mary Elizabeth Alexander; the couple would have five children. The 1880 federal census shows the Winstons living and farming in Campbell County, Virginia. Charles J. Winston died on March 16, 1889, and was buried in Winston-Clark Family Cemetery.

Ambrose W. Winston