Five family portraits of five family members, most from different branches of the same family tree. The owner knew the names of four of the sitters, but not the names of the five artists. Here are the paintings:
Two of the artists were familiar friends, so familiar that I recognized their work almost instantaneously. But, that “blink” moment always needs to be proved — or disproved — with facts. In the case of Mary Elizabeth Lee (Mrs. Robert F. Fleming), proof was especially easy: Manuel Joachim de Franca (1808-1865) signed his name, as he usually did. For the four other portraits, I followed my methodology of learning about the subject and establishing “when” and “where,” which usually leads to possible artists. The investigation began with the first painting.
Henry Lee II
The portrait of Henry Lee II (1729-1787) is thought to have been painted from a miniature by Alice Matilda Reading (1859-1939). The Virginia Historical Society owns a nearly identical portrait of Henry Lee II by Reading.
The Lee family, John Adams wrote, “had more men of merit in it than any other family.”[i] Henry II’s cousins included Thomas Ludwell Lee (1730-1778), Richard Henry Lee (1732-1794); Francis Lightfoot Lee (1734-1797), William Lee (1739-1795), and Arthur Lee (1740-1792). Each of them contributed to the American Revolution and helped create the new nation whether by serving in the Virginia legislature, the Continental Congress, the Constitutional Convention, or on diplomatic missions. Henry Lee II was a member of the Lee family of Virginia. Henry Lee II was the son of Henry Lee I (1681-1747) and Mary Bland (1704-1764), whose maiden name would carry through the family through at least six generations. Henry Lee II was a member of the Virginia legislature and a friend of George Washington (1732-1799). According to family legend, and a story by Washington Irving, both the future president and Henry Lee II vied for the hand of Lucy Grimes [Grymes]. She married Henry. Their oldest son, Henry Lee III, better known as Revolutionary War hero “Light Horse Harry” Lee. He, in turn, sired, Robert E. Lee (1807-1870), leader of the Confederate forces during the Civil War.
In the portrait, Henry Lee II appears to be a young gentleman in his mid-20s, but since portrait artists nearly always drop at least ten years from the age of the subject, he could have been in his mid-30s. Or, if Lee asked the artist to add maturity to a youthful countenance. as portrait subjects sometimes did, he could have been in his early 20s, So, the date of execution could range from approximately 1750 to 1770, Lee’s clothing, however, best fits the mid-1850s.
His home, Leesylvania in Prince William County, Virginia, was located not far from the Potomac River, which facilitated travel to other regions, such as Williamsburg, for political or social activities.
Given the prominence of the Lee family, the artist must have been one of the better painters of his day. Gilbert Stuart (1755-1828) portrayed two of Henry Lee II’s sons, Charles Lee (1758-1815) or Gentleman of the Lee Family and Major General Henry “Light Horse Harry “Lee (1756-1818). The resemblance between Colonel Henry Lee II (1729-1787) and the portrait of Charles Lee or Gentleman of the Lee Family is striking. But the resemblance is familial, not artistic. From Stuart’s birth on December 3, 1755, until his departure for the British Isles in 1771, he lived in Narragansett, Rhode Island, some 500 miles from the Lee family estate. Lee died six years before Stuart returned to the United States in 1793 so Stuart was not the artist. He was also too young.
Charles Willson Peale (1741-1827) portrayed several of Henry II’s cousins. Their portraits hang at Independence National Historic Park, Philadelphia, Pennsylvania,But the portrait does not fit Peale’s distinctive style, and Peale too, was too young. In tidewater Virginia in the the mid-18th century, the two most probable artists were John Wollaston (ca. 1710-ca. 1775) and John Hesselius (1728-1778).
Wollaston came to the Williamsburg region in 1755 and remained in the area for two or three years, sometimes traveling to various plantations. Hesselius, a native of Philadelphia, came under Wollaston’s influence when he worked along the east coast from New Jersey to Maryland from 1856-1859. In comparing examples of their work with the portrait of Henry Lee II (Figure 11-Figure 18), the portraits by Wollaston showed similarities in the eyes and in the strong jawline. Hesselius’ work bore a superficial likeness, but the faces of his subjects have an odd circular countenance with the forehead tilted back and chin thrust forward.
It is impossible to know definitively, especially since Henry Lee II is a copy, but John Wollaston may have painted the original portrait of Henry Lee II, the father of General Henry “Harry Light Horse” and the grandfather of General Robert E. Lee.
The next portrait, chronologically was Woman in Red. Who was she and who was the artist who portrayed her?
 Richard B. McCaslin, Lee In the Shadow of Washington (Louisiana State University Press, 2001), 15.
 Ibid, 15-18. For a synopsis of Lee family histories, “Meet the Lee Family,” Stratford Hall, Home of the Lees of Virginia and Birthplace of Robert E. Lee, http://www.stratfordhall.org/meet-the-lee-family/ , accessed August 2016; See also, among many published works, Paul C. Nagel, The Lees of Virginia: Seven Generations of an American Family (Oxford University Press, USA, 1990); Louis W. Potts, Arthur Lee: A Virtuous Revolutionary (Louisiana State University Press, 1981).