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Pirates of the American Revolution

February 27, 2026

ELEUTHERA, Bahamas—On March 3, 1776 – 250 years ago next week – Commodore Esek Hopkins of the new U.S. Continental Navy sailed to the Bahamian island of New Providence, just 50 nautical miles due west of here in the Caribbean Sea.

He commanded a small fleet, hastily assembled and sailing under the American flag. The target was the British garrison at the port of Nassau and the military supplies stored there. Nassau was only lightly defended, and Hopkins, with a force of roughly 200 American marines, captured 24 casks of gunpowder, 103 artillery pieces, and significant other war-making provisions – all without a single loss of American life.

It was the first amphibious assault by the brand-new US Navy, and an auspicious birth to what would grow to become the mightiest naval power the world has ever known.

Sailing with Hopkins were two men who would become maritime legends of the Revolution: Samuel Nicholas, the founder of the United States Marine Corps, and John Paul Jones, “the father of the U.S. Navy,” who, even as the ship foundered beneath him, famously told the British, “I have not yet begun to fight.”

Both men will be honored during America’s 250th celebration, and rightfully so. But there is another group of revolutionary naval heroes who should also be remembered, who did more to win our nation’s independence than Nicholas and Jones combined. Their story is seldom told, perhaps because they never served in uniform, never obtained an officer’s rank, and never swore an oath of allegiance to the U.S. government.

These were the men the British called “American pirates,” even though the Crown knew better. More accurately, they were “privateers,” manning ships licensed by the fledgling governments of the Eastern seaboard to attack British shipping. They sailed for coin as well as country, entitled to a share of anything they captured. It was an enticing proposition: Fortunes could be won if the wind was right, the captain brave, and the crew willing.

An estimated 1,700 ships and boats joined this multifarious armada. They came in all sizes, ranging from the 100-foot-long Caesar, which hailed from Boston and carried a crew of 200 men, to the lightly manned 28-foot whaleboats that prowled Long Island Sound. The fleet came to dwarf the U.S. Navy, which outfitted a total of only 65 vessels over the entire course of the war.

Despite their lack of command and control and their commercial motives (or maybe because of them), the roughly 20,000 men who sailed aboard American privateers ended up making an enormous contribution to the war effort. They denied British troops vital supplies, weapons, and ammunition. They drove up the cost of maritime insurance in London, increased the prices of imported goods, and thereby helped turn British public opinion against the war.

They impressed into service British seamen and a few Americans as well (much to the displeasure of John Paul Jones, who, after taking command, soured on what he viewed as amateur involvement in naval affairs).

But Benjamin Franklin was a fan; George Washington was an investor. In a letter to his wife, Abigail, in the spring of 1777, John Adams sounds practically giddy as he reports on the adventures of two famous American privateers:

“Have you heard of the Success of the Rattlesnake of Philadelphia, and the Sturdy Beggar of Maryland…These two Privateers have taken Eleven Prizes, and sent them into the West India Islands.”

Forty years after the victory at Yorktown, Adam wrote that the colonial privateering acts passed by the Province of Massachusetts Bay were “one of the most important documents in history. The Declaration of Independence is brimborion in comparison to it.” (That’s an archaic French word for “useless or valueless object.”)

With their swagger and independence, these revolutionary privateers might seem uniquely American, but they were in fact part of a long tradition. Ever since the Middle Ages, kings and queens of Europe had augmented the efforts of their official navies by issuing “letters of marque” to private vessels, thereby creating what have derisively called “pirates with papers.”  

For ship owners, captains, and crews, privateering was lucrative and exciting work. And when peace occasionally broke out and government revoked their letters of marque, some refused to stand down and opted to continue their pillaging ways – crossing that thin line that has always delineated privateer from pirate.

Privateering reached its height during America’s early colonial period. European empires were frequently at war, each seeking to carve its place in what (to them) was the New World. When Britain and Spain ceased their hostilities at the end of the War of Spanish Succession in 1714, an unsettling number of Caribbean privateers went rogue.

It ushered in the last chapter in what historians describe as the “Golden Age of Piracy,” which lasted roughly from 1650 to 1725. In seaport towns from Maine to Jamaica, the pirates of this period are remembered to this day: Henry Morgan, “Black Bart” Roberts, “Calico Jack” Rackham, Anne Bonny, Charles Vane, and, of course, Edward “Blackbeard” Teach. 

These pirates played a role in America’s colonial life. Blackbeard established a cozy and mutually beneficial relationship with North Carolina’s Gov. Charles Eden. Lower Manhattan crawled with pirates, including the notoriously successful “Captain Kidd,” who owned a mansion on Pearl Street, as well as several other fine city properties. My own ancestors had to flee their farm on Fishers Island in Long Island Sound in the 1690s, escaping pirates who occupied nearby Block Island and, according to legend, buried treasure there.

Kent Island on Maryland’s Eastern Shore, where I live today, was given its name by William Claiborne, an early 17th-century English sailor and trader. He was also the first pirate to ply the Chesapeake Bay, attacking settlers and shipping from the new colony of Maryland, which claimed Kent Island from the more established colony of Virginia.

As one can imagine, the difference between a pirate and a privateer was mainly in the eyes of the beholder. Samuel Taylor Coleridge wryly observed, “No man is a pirate, unless his contemporaries agree to call him so.” But the stakes for these perceptions could literally be the difference between life and death.

Privateering was a capricious trade – especially when one’s backers didn’t stay loyal. Historian Richard Zacks makes a convincing case that Captain Kidd was really a privateer, not a pirate, but that his fate was sealed when he was double-crossed by powerful nobles in Britain who’d hired him. Kidd was arrested and sent to London to stand trial, and met the fate of many pirates: He was hanged, tarred, and “gibbetted,” which means his body was displayed in an iron cage at the mouth of the Thames as a discouragement to all would-be pirates.

The temptation to cross the line from privateer to pirate was always strong. But Eric Jay Dolin, author of “Rebels At Sea: Privateering in the American Revolution,” concludes that most American privateers did stay on the right side of the law and at war’s end, returned to peaceful life and spurned the lure of piracy.

Which isn’t to say that there weren’t excesses. Dolin offers a provocative argument that if it weren’t for the gluttony of American privateers on the coast of what would later become Canada, the new nation forged after 1776 would likely have had at least one additional colony.

In those days, the Maritimes seemed a natural part of the new United States. The British had largely expelled the French from Nova Scotia, and the Crown encouraged immigration from North America. Three-quarters of the island’s population were transplanted New Englanders, largely sympathetic to the cause of independence.

They made overtures to the Continental Congress about joining the revolution. But the American privateers so harassed their ports and shipping that public opinion turned, and Nova Scotians decided to remain British. As one islander wrote at the time, “Robbing poor innocent ones has been a great means to cool the affect of many well-wishers to the just proceedings of America!” (Donald Trump, take note.)

The Founders nonetheless emerged from the war convinced that privateering was an essential tool to the survival of the American experiment. In fact, they wrote it into the Constitution: Article 1, Section 8 authorizes Congress to “grant letters of Marque and Reprisal.” The French pirate Jean Laffite turned American privateer during the War of 1812 and helped General Andrew Jackson win the Battle of New Orleans. While President Lincoln didn’t issue letters of marque during the Civil War, Jefferson Davis did on behalf of the Confederacy. To this day, privateering remains a legal option in the United States, which for more than two centuries has rejected international efforts to outlaw the practice.

In this light, the geopolitics of America’s 250th year seem both strange and strangely familiar. A U.S. president talks lustily of invading Greenland, retaking the Panama Canal, and annexing Canada. Houthi “pirates” ply the Red Sea, attacking international shipping (although given our own history, we might more charitably view them as, ahem, “privateers” in service of Iran.)  America gathers a fleet to remove the leader of Venezuela, which then steams off to pressure the Iranian mullahs.

Gunboat diplomacy is back, but gunboats are few and far between: The U.S. Navy has shrunk to just 241 active ships, 163 of which are cargo or support vessels. Today’s strategists debate whether America can continue to project enough naval power to keep the peace, let alone prevail if a global shooting war breaks out.

Privateers, anyone?

This article was originally published by RealClearPolitics and made available via RealClearWire.

Andrew Walworth is chief content officer for RealClearPolitics, moderator of RCP’s daily radio show on SiriusXM, and keyboardist for Good Talk Russ, the hottest band on Maryland’s Eastern Shore.

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