Light-Horse Harry & Robert E. Lee: The Lees of Leesylvania
Light-Horse Harry & Robert E. Lee: The Lees of Leesylvania  
Podcast: The Old World with Will Tanner
Published On: Wed Aug 05 2026
Description: This is the story of the family that produced Light Horse Harry and Robert E Lee: the Lees of Leesylvania, the Virginia branch of the Lee family that produced a long line of planters, soldiers, politicians, and lawyers. In it, I contrast the Leesylvania Lees with the Stratford Hall Lees and show how the Leesylvania line developed its own place in Virginia history as some of the greatest and most memorable members of the gentry through landholding, public service, and military command. Listen ad-free here: https://www.theamericantribune.news/p/light-horse-harry-and-robert-e-lee  The story begins with Henry Lee I, the founder of the Leesylvania line. Born to Richard Lee II and Letitia Corbin, he became a major tobacco planter and militia officer who managed plantations, defended the Northern Neck, and expanded into frontier lands along the Potomac. He established holdings at Freestone Point and later developed the area that became Leesylvania. Henry Lee II then turned that inherited tract into the family seat. After marrying Lucy Grymes, the famed "Lowland Beauty" whose hand he won despite competition from George Washington, he built the house at Freestone Point and named it Leesylvania. The estate became a large plantation complex with scientific management, crop rotation, domestic production, commercial fishing operations, pork and corn production, and horse breeding. Henry II also served as a county leader and burgess, and Leesylvania became a social and political gathering place that often hosted George Washington. The episode then turns to the children of Henry Lee II and Lucy Grymes, especially Henry Lee III, Charles Lee, Richard Bland Lee, and Edmund Jennings Lee. Henry Lee III became Light Horse Harry, a Revolutionary War cavalry commander famed for his leadership of "Lee's Legion" and one of Washington's favorites. Charles Lee became attorney general under George Washington and John Adams. Richard Bland Lee helped shape the compromise over federal assumption and the site of the national capital. Edmund Jennings Lee became mayor of Alexandria and a long-time defender of the Episcopal Church. The final section traces the family's decline after Henry Lee II's death, the burning and loss of Leesylvania, and the dispersal of the family into Alexandria. It then looks ahead to later generations, including Sidney Smith Lee, Robert E. Lee, Custis Lee, Rooney Lee, and Fitzhugh Lee, showing that although the estates disappeared, the family's military and public legacy remained part of American history. CHAPTERS: 0:00 The Lees of Leesylvania: The Other Lees 3:07 Henry Lee I 9:45 Leesylvania Takes Shape Under Henry Lee II 18:42 Life at Leesylvania: Commerce, Horses, and Hospitality 29:32 The Revolutionary Generation Of Leesylvania Rises 39:39 Sydney Smith Lee's Crazy Naval Career 45:49 Harry's Fall and Robert Lee 48:09 The Lee Family During the Civil War and After It 51:18 The Final Years and Legacy of the Leesylvania Lees   Sources Referenced in this Episode: I am an Amazon Affiliate. If you would like to support the show at no added cost to yourself, you can do so by using the links below to order and read the sources I used to create this episode. Thanks!   Cole, Ryan, Light-Horse Harry Lee: The Rise and Fall of a Revolutionary Hero, https://amzn.to/4xltuvc Connelly, Thomas Lawrence, The Marble Man: Robert E. Lee and His Image in American Idea, https://amzn.to/4hOR3bg Crocker, H. W., III, Robert E. Lee on Leadership: Executive Lessons in Management, https://amzn.to/3Ruayvi Dowdey, Clifford, Lee: A Biography, https://amzn.to/4wBOgH2 Evans, Emory G., A Topping People: The Rise and Decline of Virginia's Old Political Elite, https://amzn.to/4z6IUFB Flood, Charles Bracelen, Lee: The Last Years, https://amzn.to/4xnlZ7g Freeman, Douglas Southall, R. E. Lee: A Biography, https://amzn.to/4q4w3Qc Gamble, Robert S., Sully: The Biography of a House, https://amzn.to/4hzPvSH Hendrick, Burton J., The Lees of Virginia, https://amzn.to/3SfHPdN Lee, Cazenove Gardner, Jr., Lee Chronicle: Studies of the Early Generations of the Lees, https://amzn.to/4fQm5Ns Longacre, Edward G., Fitz Lee: A Military Biography of Major General Fitzhugh Lee, C.S.A., https://amzn.to/4hh1xQx McGaughy, Kent J., Richard Henry Lee of Virginia: A Portrait of an American, https://amzn.to/4fHyJ2s Nagel, Paul C., The Lees of Virginia: Seven Generations of an American Family, https://amzn.to/4gapiZz Thomas, Emory M., Robert E. Lee: A Biography, https://amzn.to/4bQL1U3 Unger, Harlow Giles, First Founding Father: Richard Henry Lee and the Call to Independence, https://amzn.to/4pYIsop