Ed Hynes’s presentation examines the largely overlooked naval and irregular warfare conducted on Long Island Sound during the American Revolution. Drawing on local records and Kimberly Goodling’s 2021 doctoral dissertation, Hynes argues that privateers played a far more important role in the American victory than traditional histories acknowledge.
The geography of the Sound shaped the conflict. British forces occupied Long Island, while Patriot-controlled Connecticut lay less than ten miles away in places. Connecticut’s numerous shallow harbors protected small, maneuverable whaleboats from larger British warships. Crews—often experienced sailors, traders, and shipbuilders—used these boats to cross the Sound at night, raid farms and ships, capture prisoners, smuggle goods, and gather intelligence.
Privateers were essentially government-licensed pirates. After posting a bond and receiving authorization from Connecticut or the Continental Congress, they could seize British ships and property. Courts were supposed to determine whether captures were lawful and divide the proceeds between the government and privateer crews. The prospect of profit attracted sailors who might otherwise have joined the poorly paid Continental Navy. Privateering also had strategic value: captured supplies and weapons supported the Continental Army while depriving British forces in New York. According to evidence cited by Hynes, Patriots captured seven British supply vessels for every ship Britain seized, causing marine-insurance rates at Lloyd’s of London to soar.
The struggle was also a bitter civil war. Connecticut expelled many Loyalists in 1775, while Patriots fled British-occupied Long Island after 1776. Families and communities divided, and former neighbors repeatedly attacked one another. Notable episodes included the British destruction of Danbury’s supply depot; Return Jonathan Meigs’s successful raid on Sag Harbor; the kidnappings and eventual exchange of Patriot General Gold Selleck Silliman and Loyalist Judge Thomas Jones; and the 1781 destruction of New London and Groton under Benedict Arnold.
Locally, Loyalist Captain Frost’s raid on the Middlesex meetinghouse—present-day Darien—demonstrated careful planning around darkness and tides. His force captured 49 men and 40 horses, transported them through the Fish Islands, and later returned to seize livestock.
Hynes concludes that violence on the Sound continued even after Yorktown because the conflict had become intensely personal. Privateering materially weakened British supply lines, but it also produced fear, retaliation, displacement, and lasting divisions along both shores.
Ed Hynes, CFA was born and raised in Wilton, CT. He attended Wilton High School where he played both football and lacrosse. In 1977 Ed graduated from The George Washington University in Washington D.C. with a B.A. in Political Science. He subsequently spent most of his career in financial services. As an equity analyst, institutional salesperson and trader he worked with some of the premier investment banking firms in many of the world’s leading financial centers including New York, Tokyo, London, Chicago and San Francisco. In 2001 Ed became a Chartered Financial Analyst (CFA) charter holder, and is currently a Financial Advisor with Merrill Lynch in Westport, CT. He lives in Norwalk.
Ed first became interested in the Revolutionary War as a child when he learned his neighbor’s house was partially burned by the British during the Danbury Raid in 1777. Fascinated by history, he and his late wife visited many important battlefields both here and abroad. Ed has spoken to the DMA before – 2013 on the Battle of Ridgefield, 2019, about the War on Long Island Sound and again in 2020 on the Origins of the Star Spangled Banner.
