The year 2026 marks the 250th anniversary of the Declaration of Independence. Cardinal News has embarked on a project to tell the little-known stories of Virginia’s role in the march to independence. This project is supported, in part, by a grant from the Virginia American Revolution 250 Commission. Find all our stories from this project on the Cardinal 250 page. You can sign up for our monthly newsletter:
Captain John Sinclair could hold a grudge. Mostly, it was the English he despised, but he wasn’t picky; even family was fair game for his cold shoulder.
It was this long memory that in a way made Sinclair an unsung hero of the American Revolution — and almost cost him his personal freedom in the early days of the republic. Sinclair’s story is one of talent and daring, accusations and betrayal. He was a seemingly fearless seafarer who contributed unconventionally to American independence while forging a personal and professional life of moral complexity. The memory of Sinclair has largely been obscured by time, yet in all his eccentric glory, he is emblematic of the country the war for independence established: passionate, bohemian, resolute.
It’s an odd turn of fate that Sinclair’s story is not well known. His descendants number in the thousands. You might have met one without knowing it. You certainly know of one: Award-winning actress Glenn Close traces her lineage back to Sinclair.
His ample progeny starts with a humble Virginia upbringing. He was a scrappy lad, born in 1755 in Hampton to a father who had been kidnapped from Scotland and raised in the Old Dominion. Evidently Sinclair’s father, Henry Sinclair, had no love for British nobility; the death of a couple elders in Scotland meant that Henry became the rightful Earl of Caithness, but he refused to return to accept the title.
John Sinclair grew up as a merchant seaman, learning the trade from his father. Tall and comfortable in the rigging of ocean-going ships, Sinclair was known to have a temper and developed the sort of extravagant cockiness that often washes over young sailors. His hubris might have been well deserved; by his late teens, he was commanding his own merchant vessel.
Carter Sinclair is a Virginia Beach resident and the fourth-great-grandson of John Sinclair who has heard family lore about the captain his whole life. “He was a self-made man,” he says. “His father was kidnapped from Scotland, he probably didn’t have much and wasn’t a member of the gentry. He was very successful, but also very strong-willed and opinionated.”
As for why Captain Sinclair detested the English, it could stem from negative interactions with British merchants or naval forces in Hampton as the Colonies careened toward war. Truth be told, we’ll never know. Sinclair’s life is only modestly documented, according to Thomas Wiatt, author of “Alleged Pirate: The Legend of Captain John Sinclair of Smithfield and Gloucester, Virginia.”
“Some of the stories are probably not 100% true,” Wiatt said.
Wiatt is also a descendant of Sinclair. The family connection compelled Wiatt to write a book about him, but so, too, did the captain’s relative obscurity. “I try to write about people in history who haven’t gotten as much publicity,” he said.
Wiatt, who lives in Newport News, said Sinclair is often known among descendants as “Captain John.” Stories were told and retold through generations, and like the game telephone, likely took on new details with each recounting. But the outlines of solid oral tradition have filtered through time, and there’s enough historical documentation to recount Sinclair’s remarkable story.
The seawater that coursed through Sinclair’s veins was a valuable asset as the nation stood on the cusp of revolution. In 1774, he moved to Smithfield, a small port town on the southern bank of the upper James River, and there he married Anne Wilson. Their home still stands on South Church Street today. In Smithfield, Sinclair purchased the St. Andrew, the first of many vessels he would eventually own.
Two years later and just months before the Declaration of Independence, Sinclair put the St. Andrew and two other vessels he owned into the service of the Virginia State Navy. The Royal Navy at the time was the most fearsome maritime force in the world. Congress authorized the creation of the Continental Navy, but against such a well-armed adversary, American sailors didn’t have a prayer. So, Virginia, along with ten other Colonies, formed their own navies to help wage war at sea.
Because Virginia State Navy vessels were comparatively small, going head-to-head against a Royal Navy warship was out of the question. Instead, the commonwealth’s vessels were used to slip valuable military supplies through British blockades and harass merchant ships.
Sinclair excelled at these tasks. As a captain in the Virginia State Navy, he was known for an uncanny ability to outmaneuver British chase boats meant to enforce blockades. Sinclair successfully delivered cargoes of supplies and information. These skills also came in handy for privateering.
Privateers were an important component of the American war effort. They were something akin to government-sanctioned pirates — armed vessels that chased down and confiscated the cargo of civilian enemy merchant ships. The techniques privateers employed wouldn’t pass muster today. They’d often approach a ship under a false flag and captain and crew would get a large cut of the captured loot. Hundreds of American vessels engaged in privateering, all with official government sanction.
Much like his expertise as a blockade runner, Sinclair excelled at privateering. He received the official go-ahead — called a Letter of Marque — from the Continental Congress in October 1776 and soon found success.
Sinclair biographer and descendant, the late Claude Lanciano, wrote in “Captain John Sinclair of Virginia: Patriot, Privateer, and Alleged Pirate,” that Sinclair never applied for government compensation for serving in the war because his profits from privateering were so substantial. “He took prizes both early and consistently over the war’s duration,” Lanciano wrote.
Carter Sinclair grew up hearing that his great-great-great-great-grandfather was a pirate, which he said is not really true, even if family lore sometimes embellished the role he actually played as a privateer. What was undoubtedly the case was his prowess at the helm. Carter Sinclair has sailed into Caribbean ports just as his ancestor did. “He was a seaman who was a really great sailor,” he said. “I feel a strong connection to him with my love of the water.”
So masterful was Captain Sinclair’s skill at evading enemy ships during the American Revolution that the Marquis de Lafayette tasked him with delivering a crucial message to naval forces of France, which joined the war in 1778. Sinclair slipped through a British blockade of Hampton Roads twice, a feat for which the French Navy presented him a ceremonial sword as a token of appreciation.
Sinclair’s affinity for seafaring — and for privateering — continued after Americans won independence. Not even seaborne tragedy could squelch his yearning for the chase. In 1790, Sinclair, by then the father of two sons and two daughters, took his six-year-old, William, along on a trading voyage to the West Indies. When the vessel started taking on water during bad weather, Sinclair ordered the crew to abandon ship. William did not survive the ordeal. As if that didn’t cut deeply enough, Sinclair returned home to Smithfield only to find out that his wife, Anne, had died while he was at sea.
In 1793, France and Britain were at war, and Sinclair, newly remarried, sensed an opportunity to resume the skill he had honed so well during the American Revolution. The following year, Sinclair began outfitting a merchant ship he owned, the Unicorn, with the accoutrements of privateering, apparently with the idea that he’d confiscate British merchant ships on behalf of France, once again stoking his enduring hatred of all things English.
But there was a glaring issue: The government of the United States had passed the Neutrality Act, which outlawed American citizens’ involvement in foreign wars. State and federal officials went to Smithfield to see for themselves. What ensued was a game of cat and mouse. Sinclair removed guns and ammunition. He made an excuse when asked why the decks were being modified. The U.S. Army seized the Unicorn and arrested Sinclair.
In the end, Sinclair came out ahead. On the charge of outfitting the Unicorn for privateering, a jury in Williamsburg acquitted him, with historians suggesting his status as a war hero playing a part in the decision. The government returned the ship to him. Nevertheless, the whole ordeal caused a rift that cleaved the Sinclair family forever.
Prior to the Unicorn affair, Copeland Parker, a local government official, had asked Sinclair for his daughter Elizabeth’s hand in marriage, and he concurred. But it was Parker in 1794 whom state officials tasked with investigating the illicit transformation of the Unicorn, which he reported truthfully as duty demanded.
Sinclair was enraged. He forbade Elizabeth from ever speaking to Parker again, but the forbidden fruit was too tempting a prize, and when Sinclair sailed for the West Indies on a trading voyage, the young couple eloped. Sinclair never spoke to his daughter again and demanded his family stop communicating with them. At his death, he bequeathed his daughter’s family one dollar.
“Forgiveness and forgetfulness were not among his traits,” said Ben Rhodes, Sinclair’s fifth-great-grandson.
Just weeks after excommunicating his daughter, Sinclair moved to a sprawling riverfront property in Gloucester County he named Lands End and built a brick dwelling which still stands today.
Rhodes lives in a home called Bay Cottage on Sinclair’s onetime property. He said it’s important to note that for all Sinclair’s eccentricities, he was a hero of the American Revolution and the patriarch of a family that would go on to accomplish great things in the nation he helped to found.
“I would hope he is remembered most as a patriot and a privateer,” Rhodes said. “A lot of the Sinclairs are entrepreneurs. The family includes civil engineers and doctors. A lot have gone on to do extraordinary things. I will always remember him as being a patriot and leading a successful family.”
