Meanwhile, Henry received an education appropriate to his class, including when he was nine years old and Thomas ten, beginning studies at the College of William and Mary in Williamsburg.

Although the position involved some military responsibility, because raiders from other nations were rare in the era after Queen Anne's War, the post was considered mostly as lucrative, since the holder earned a 10% fee based upon collection of a tax on tobacco being shipped out of the colony.

This agricultural activity became particularly important as Thomas became more involved in politics and spent time in England and Williamsburg as well as the Virginia colony's western reaches.

During this time, Thomas and Henry Lee also bought commercial sites upstream on the Potomac River, mostly within the Northern Neck proprietary.

[7] In 1729, the Machodoc house was destroyed in an arson fire[8] set by disgruntled "Felons who Thomas [Lee], as Justice of the Peace, had condemned.