Whitley is first mentioned as a public figure in the Second Charter of Virginia on May 23, 1609, where he is said to be one of the members of the third supply mission to the colony of Jamestown. In 1622 Whitley survived an attack on Jamestown known as the Jamestown Massacre, in which the Powhatan Indians, led by Chief Opechancanough, killed over 347 citizens of the town.
In 1600 Whitley married Elizabeth Farrer and had the following children.
- "The Second Charter of the Virginia Company of London". Learner. Retrieved 10 June 2015.
- Shelton, Kenneth. "Colonel Thomas Whitley". wikitree. Retrieved 10 June 2015.