When revolutionary fervor grew with resistance to the
Stamp Act, McDougall became active in the
Sons of Liberty, and later was their leader in the city. Difficulties in the city and colony were increased by the
Quartering Act, which required the colonists to provide housing and support to the British troops. The colony's assembly had refused to pass appropriations for their housing in 1767 an 1768, and been prorogued. Then the new assembly of
1769 approved money for their support. McDougall wrote and had printed an anonymous broadside,
To the Betrayed Inhabitants, which criticized the vote. He was accused of libel and arrested on
February 7, 1770, but refused to post bail, so he was jailed. He spent two periods in jail, for a total of about five months, but wasn't convicted. His imprisonment became another cause for protest, and his wife Hannah led marches down Broadway to the jail. He had so many visitors that he had to schedule appointments. The protests led to his release, but he was re-arrested later and jailed again. Finally, the new governor
William Tryon ordered his unconditional release.
McDougall became the street leader of the Sons of Liberty, and organized continued protests until the city was finally fully occupied by the British in 1776. He organized the city's reaction to the Tea Tax in
1773 and led their action, similar to the
Boston Tea Party. He became a member of the Committees of Safety and Correspondence, and when New York established their revolutionary government in 1775, he was elected to the provincial Congress.
McDougall Street in the
New York City borough of
Manhattan is named for him.