His ship taken (and subsequently re-named Jamaica for service as a British warship); his crew impressed, imprisoned or scattered, and himself confined as a prisoner of war in the old fort at Montego Bay, Captain Gideon Olmsted had suffered cruel reversals as a privateer. He endured a month of summer swelter in the fort before is circumstances changed. The British armed sloop Active, Captain Underwood Commanding, had but 6 guns and a crew of 14 and lacked an experienced pilot to navigate the reefs of the Bahamas on a voyage to resupply the British in New York. Captain Olmsted had just this knowledge from his peacetime voyages in the West Indies, and so one day he found himself brought before the owner of the Active, along with the Captain of the vessel, and offered a "compulsory" berth as second mate and trade captivity in the tropics for confinement in New York at the end of the voyage.
So it was that Olmsted and three other American prisoners, all Connecticut men but from a different ship than the poor old Polly, sailed on the Active bound for New York. The cargo included rum, coffee, pimento and manufactured goods. Provisions included sheep, goats, pigs, fowl and three large sea turtles. They traveled in convoy lead by the Glasgow, and with Olmsted's assistance made their way safely through the Bahamas and even outdistancing many in the convoy as they rounded Cape Hatteras. To all outward appearances, Olmsted was a model prisoner. Inside, he had no intention of rotting away in a prison hulk in New York harbor.
The Glasgow turned loose her charges on August 27th to make their way to New York under light escort, and Olmsted bided his time until the opportunity to strike presented itself. It happened when they were on a course for Long Island, when Olmsted and seven picked men stood the watch shortly after midnight on September 6th, 1778. His men, including the three Americans and others deemed the least threatening of the British crew had just come on deck when Olmsted ordered the gangway and afterhouse lashed tight. A 4 pound gun and a swivel were aimed at the gangway and Olmsted spun the wheel and headed for Egg Harbor, New Jersey.
The Captain and two of the men below soon fired pistols through the companionway, wounding Olmsted but not disabling him, and threatened to blow up the ship if he did not surrender. After daring each other to do their worst, Olmsted ordered the four pounder to fire into the cabin, and the fight continued for another day. Spoons were melted for bullets, and efforts made to wedge the rudder, but by September 8th the British crew surrendered and the ship was Olmsted's prize.
It was an extraordinary feat of daring and heroism, but the laurels were soon to be snatched away, only this time by their own countrymen. They were off Cape May when they encountered brig Convention, a Pennsylvania privateer under Captain Underwood that escorted them into Delaware Bay and on this basis claimed the Active as their prize. Another privateer that was in the area when they sailed into the Bay also filed a claim, and The Philadelphia Admiralty Court under Judge George Ross, a Signer of the Declaration of Independence moved to condemn and sell the cargo even before Olmsted had the chance to make his claim.
Olmsted appealed this verdict and made his case for the Active as his lawful prize. His prisoners all testified that he and not the Pennsylvanians had taken the ship, but a verdict awarded 3/4 of the proceeds to the Commonwealth of Pennsylvania and her native claimants, and but 1/4 to Olmsted and his men. Olmsted appealed directly to the Court of Commissioners of Appeals of Congress, which on December 15th, 1778, ruled that the entire proceeds should be paid to Olmsted and the men who had seized the Active, but this was by no means the end of things, but only the beginning.
Olmsted's champion during his appeals was the military commander of Philadelphia, his fellow Nutmegger General Benedict Arnold. Among the charges of misconduct subsequently brought against Arnold by Joseph Reed, President of Pennsylvania, was that his unworthy involvement had likely caused "the delay of justice in the courts of appeal." This charge was dismissed as baseless but itself may have contributed to the erosion of Arnold's patriotism.
The value of the prize had been appropriated by the Commonwealth of Pennsylvania, converted to bonds and held by Judge Ross, the treasurer of Pennsylvania, who subsequently died in 1779. As far as the Pennsylvania authorities were concerned, Ross held the bonds in a private capacity and they became embroiled in the settlement of his estate. Olmsted has by this time returned home and then put to sea once more, and still had not received his full and lawful share. He continued to fight for his claim for decades after the war was concluded, and it was not until 1809 that those who in the meanwhile had conspired to keep him from receiving his award were found guilty (and subsequently pardoned by President Madison). Olmsted still maintained claims against Pennsylvania of roughly $30,000 at the time of his death in 1845.
All that was in the future. In 1779 he commanded the Connecticut privateer Gamecock, and then in the Spring of 1780 he was master of the sloop Hawk, and during a successful cruise primarily in Long Island Sound he took several prizes, including the Brig St. Andrew. That September he commanded the schooner Raven, and had another successful cruise. But it was in 1782 that he set sail in command of the brigantine Nathaniel Greene (16 guns), only to be attacked well east of Nantucket Shoals by the British privateer Virginia (24 guns) , commanded by Captain Stanton Hazard of Halifax, and compelled to strike. Olmsted was taken prisoner to New York, thus ending his revolutionary war service, but continued as a mariner and and unwavering defender of his legal claims against Pennsylvania, for many more years to come.
He was 96 years old when he died.