Home Connecticut Captain Gideon Olmsted Fights the American Revolution – For 30 Years

Captain Gideon Olmsted Fights the American Revolution – For 30 Years

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Gideon Olmsted, a Connecticut sea captain, departed Hartford and put to sea in December 1777 with a cargo of horses, onions, tobacco, barrel hoops and bricks. He sailed his ship, the Seaflower, to Guadaloupe. There he off-loaded his wares and took on a cargo of molasses, coffee, tea and salt. But on his return trip to Connecticut, in April of 1778,  the British warship Weir seized the Seaflower.

Gideon Olmsted as an old man

The capture of Olmsted’s vessel would lead to bloody battles at sea, near-civil war in Pennsylvania, a 32-year legal fight and the publication of a long-lost journal by Olmsted’s great nephew, Frederick Law Olmsted.

It also resulted in a landmark legal victory that established the authority of the Constitution of the United States.

Gideon Olmsted

He was born on Feb. 12, 1749, in East Hartford. His ancestors had arrived with the dissident Puritans led by Thomas Hooker. Olmsted grew up on his father’s farm, but he found the ships plying Hartford’s crowded waterfront more interesting than agriculture.

He shipped out to sea at age 20 as an apprentice seaman. For the next five years he sailed merchant ships between the West Indies and Connecticut. Then soon after the Battles of Lexington and Concord, he and his brothers joined the 50-man East Hartford militia and marched to Boston. When the British evacuated, he went home and started looking for a ship.

In July 1776, he bought a one-third share in the Seaflower, a 75-ton sloop. But that’s all he and his partner could afford. The Seaflower, with no cannon, made an easy target.

The Continental sloop Providence.

Prisoner and Privateer

After the British seized Seaflower, they held Olmsted and his crew on board ships and took them to Jamaica. After a short stay in a jail, Olmsted was released at liberty. His captors had taken all his valuables and left him with only the clothes on his back.

Interior of a British prison ship

He signed onto a privateer, the 200-ton Polly, as captain. Four days after setting sail from Port-au-Prince, he encountered the Royal Navy’s Ostrich, a vessel closely matched in size, cannon and crew. After a battle in which Olmsted lost half his men, he prevailed. But just as he was about to take Ostrich as a prize, another British warship sailed into view and opened fire.

Once again, Olmsted found himself in a British dungeon in Montego Bay. It was not a good place to be, as more American soldiers died in British prisons than in battle during the revolutionary war.

Montego Bay around 1820

Impressed Into Service

In August 1778 Olmsted was put aboard the British merchant vessel Active, along with three other prisoners. The British had learned that Olmsted had often navigated the dangerous waters off the Bahamas and thought he could prove useful.

They set sail for New York from Haiti under Capt. John Underwood in a convoy bringing supplies to loyalists and British troops. The Active had the protection of a 20-gun British vessel, Glasgow, and two warships. Also in the convoy was the Seaflower, sailing for New York under its new British captain.

The Active made its way up the Atlantic Coast, approaching the Virginia shore. A friendly British privateer with 16 guns pulled alongside the Active with a dire warning. The British had left Philadelphia and the waters around the city teemed with American privateers.

Captain Underwood of the Active adjusted his course to sail well east of the coast, working north off New Jersey. Another British ship pulled alongside the Active. Its captain had more bad news. All along New Jersey, the American privateers had control of the waters.

If the Active saw any sail at all, the captain could be certain it was an unfriendly privateer because the British had blocked any vessels from leaving New York harbor. Further, he warned, an encounter with a British warship would prove equally unfriendly. The British were capturing any seamen they found and pressing them into service aboard British vessels.

gideon olmstead

Line engraving depicting the Active hove to with a fishing vessel port side of its bow. National Maritime Museum, Greenwich, England.

Victory for Gideon Olmsted

The captain of the Active adjusted course once again. He would try to reach Long Island. On deck, he mounted two small guns that he would use if small boats tried harassing him. Musket shot was brought to the deck to be ready for any fight.

Knowing they sailed in friendly waters, Olmsted and his fellow American crew members hatched a plan. The following night, as the watch changed over at midnight, the Americans put their plan in action to capture the Active. They tightly secured the companionway, sealing the captain inside. The men had assumed that there were no usable weapons below deck.  They were wrong.

A standoff followed. The captain and remaining crew fired from below deck attempting to kill Olmsted and his men. They also jammed the vessel’s rudder, restricting the ship’s movements. Captain Underwood threatened to blow up the ship’s gunpowder and send everyone to the bottom. “Do it and be damned,” shouted Olmsted.

Olmsted and his men, meanwhile, worked to seal off the cabin completely. The British melted spoons for shot, and the captain kept up his firing. Olmsted was hit in the leg. Finally, Olmsted’s men fired grapeshot with one of the small cannon into the cabin. That brought the fighting to an end. The ship’s captain agreed to cease hostilities and freed up the rudder, with promises from Olmsted to harm no one.

With that, Olmsted set course for Egg Harbor, N.J. But before he could bring the ship in, it was waylaid by an American privateer, the Convention, from Pennsylvania. Olmsted tried to convince the captain of the Convention that he should pursue the Seaflower and her rich cargo, bound for New York.

Philadelphia Bound

But the Pennsylvania captain had other plans. The Active, he said, was now his prize because Olmsted was acting without commission and thus could not legally seize the vessel. Unswayed by any arguments, the Convention led the Active toward Philadelphia.

As soon as he got off the ship, Olmsted sought out Benedict Arnold, American military commander at Philadelphia. He then explained to Arnold, a fellow Connecticut sailor, what had happened. Arnold assured Olmsted that he should have the Active as his prize, because he was acted under orders of the Continental Congress.


Benedict Arnold

The Philadelphia Court of Admiralty didn’t agree with Arnold’s interpretation. The court ordered that the proceeds from the sale of the Active should be divided. Olmsted and his fellow crew members would receive one quarter of the money. The Commonwealth of Pennsylvania, the owners of the Convention, and another vessel that was sailing in support of the Convention, would divide the remainder.

Olmsted and his compatriots were due roughly $24,000. A healthy sum. But Olmsted rejected the offer and appealed to the Congress itself for justice. Congress did, in fact, side with Olmsted. But it would take 30 more years before he received his money.

The Nearly Endless Court Battle

Pennsylvania argued that Congress did not have authority to overrule a state court. Congress, meanwhile, needed Pennsylvania’s support for the Revolutionary War. It was reluctant to press the point.

Olmsted pursued his prize for decades. Finally, in 1809, the U.S. Supreme Court ruled in Olmsted’s favor. The landmark ruling established the supremacy of federal courts. The win, though, was somewhat of a pyrrhic victory. By the time Olmsted received payment, he was 84 and the value of the Active was adjudged to be just $27,000 in total. Deducting his legal fees, Olmsted made little for the capture of the Active.

John Marshall by Henry Inman

The case, however, was a victory for the U.S. Supreme Court over the state courts. Chief Justice John Marshall read the opinion.

If the legislature of the several states may at will, annul the judgments of the courts of the United States, and destroy the rights acquired under those judgments, the Constitution itself becomes a solemn mockery, and the nation is deprived of the means of enforcing its laws by the instrumentality of its own tribunals.

By then, the claimant who held Olmsted’s share had died, and his two daughters named executrixes of his estate. The high court ordered them to give Gideon Olmsted his money. The governor of Pennsylvania then called out the militia to prevent the court order from being carried out.

In March of 1809, the federal marshal, John Smith, tried to serve the women. He met the militia’s resistance at their house. So he went back and assembled a posse of 2,000 men. After broadcasting the incorrect date on which he intended to serve them again, he and his men sneaked past the militia and arrested the two women. The Pennsylvania Legislature then caved and ordered the militia back home.

Gideon Olmsted Rediscovered

After the Civil War, Supreme Court Justice Stanley Matthews gave an address to Yale Law School in which he explained the importance of the Olmsted case. “This appears to have been the first case in which the supremacy of the Constitution was enforced by judicial tribunals against the assertion of state authority,” he said.

Gideon Olmsted by then had faded into obscurity — until the discovery of his journal in his great-nephew’s papers. The Library of Congress published his journal in 1979.

Thanks to: The Journal of Gideon Olmsted. Also Treacy, Kenneth W. “The Olmstead Case, 1778-1809.” The Western Political Quarterly 10, no. 3 (1957): 675–91. https://doi.org/10.2307/443540.  And A Privateer’s Tale: From Cannon Fire To Courtroom by Edmund H. Mahony, Hartford Courant, May 30, 2014.

Image of Continental sloop By U.S. Naval Historical Center Photograph. Painting in oils by W. Nowland Van Powell – Naval Historical Center Photo # NH 85201-KN (color), CC0, https://commons.wikimedia.org/w/index.php?curid=9103147.

This story last updated in 2022.