When he was nineteen, Tyler stood in the lobby of the colony's assembly, the House of Burgesses, and listened to Patrick Henry's speech concerning the Stamp Act 1765, which caused him both to become hostile to the British government, as well as to read law with eminent attorney Robert Carter Nicholas.

There, in addition to his private legal practice, Tyler operated plantations using enslaved labor.

[4] Meanwhile, as relations with Britain became strained, Tyler became a member of the Charles City County Committee of Safety.

He joined his forces with those led by Patrick Henry to demand the restoration of the gunpowder Virginia's governor Lord Dunmore had removed from the government magazine in Williamsburg, or else compensation.

[1][3][6] In addition to his legislative service, Tyler served as a Judge of the Virginia High Court of Admiralty from 1776 to 1788.

[2] In the debates over ratification of the United States Constitution, like George Mason and Patrick Henry, Tyler was an Anti-Federalist, ultimately voting against the document, although a narrow margin ratified it.

[2] Thus, Tyler judged some cases on his circuit with U.S. Supreme Court Chief Justice John Marshall, who had resided in Richmond and who had been a Federalist both during that Ratifying Convention years earlier, and in later elections.