The Olmsted family were among the first settlers of the Connecticut Colony. One branch went on to help establish towns like Norwalk and Ridgefield, and we descend from them. Another remained in central Connecticut, and can claim such notables as Frederick Law Olmsted in their pedigree. They can also claim this dour looking fellow, a Connecticut privateer during the Revolution whose exploits lead to one of the most notable legal battles in the early maritime of America.
Gideon Olmsted (b. 1748-49 d. 1845) began his Revolutionary service as a private soldier in George Pitkin's East Hartford Company of Spenser's militia regiment, and marched to the defense of Boston in the Spring of 1775. In early 1776, however, Olmsted , previously an apprenticed seaman, took to the sea. By the next year, he was master and part owner with his brother Aaron Olmsted and Abraham Miller, of a brand new sloop of 75 tons called the Seaflower.
Seaflower was a trim craft, but she lacked the one essential without which no privateer could flourish; she was without armament, and had great difficulty attracting a crew. When she sailed into Long Island Sound at New London on November 7th, 1777 bound for the West Indies with a cargo of horses, swine, tobacco, onions, bricks and barrel hoops and staves, he had but seven crew and no cannon. He made it to French Guadeloupe, but on the return voyage on April 6th, 1778, the Seaflower was taken by the British privateer Weir (Captain Williams commanding) and taken under a prize crew to New York.
Captain Olmsted and his crew remained prisoners on the Weir until they were eventually put ashore at Cape Francois on the Island of Hispaniola, from which they looked for opportunities to put to sea on a privateer. In June, 1778, Captain Olmsted took command of the American brig Polly, whose owner had come to the area looking for a crew and with a number of blank commissions for officers under a Letter-of-Mark. The Polly was a new vessel pierced for 16 guns. According to a 1933 biography of Captain Olmsted by Louis Middlebrook, most of the Americans in her crew were either commissioned or rated, with a Scotch sailing master, a French Lieutenant and Surgeon along with most of her petty officers and crew, a mulatto cook and even a few Spaniards. A French merchant representing the owners of the Polly sailed as supercargo, and on July 4th, 1778, the Polly put to sea from Port au Prince on a privateering cruise northward.
Four days later while cruising off Jamaica, a ship approached flying British colors. This was the ship-rigged sloop-of-war Ostrich, Captain Peter Rainier commanding: 200 tons burthen and armed with 16 carriage guns, cohorns and swivels and a crew of 110. The Polly was a brig-rigged corvette of 200 tons mounting 16 cannon (6 and 9 pounders) along with nearly 2 dozen swivels and 102 men. Olmsted, flying French colors, beat to quarters, and in response to a hail from the Ostrich, American colors were raised and a broadside unleashed.
The battle was fierce and bloody, with each ship maneuvering for advantage and broadsides blazing. The Captain of the Ostrich was badly wounded early in the exchange and the master killed. As the afternoon wore on, the Polly was able to grapple the Ostrich and board her, during which Lieutenant O'Bryan of the Ostrich survived having his throat and larynx slashed by a pike. The Ostrich caught fire and her colors were struck as many of her crew jumped overboard in expectation that the ship might explode. The Polly likewise disengaged, but the fire was suppressed and the fight resumed once more.
The Ostrich endured another 30 minutes of fighting and all but her bow guns put out of action. Yet just as victory seemed certain, another combatant entered the fray. This was the British brig-rigged 'Lowestoffe''s Prize, a 10 gun vessel that had previously been an American from North Carolina and had been captured, as her new name suggests, by the Lowestoffe, a British frigate. The prizemaster initially assigned to her had been a Lieutenant from the Lowestoffe by the name of Horatio Nelson. Now the Lowestoffe's Prize turned the tide of battle, and at last Captain Olmsted was compelled to strike. At least 36 of his crew were either dead or wounded.
Olmsted's initial voyages proved decidedly unsuccessful, and he was once again a prisoner. Yet the most remarkable exploit of his privateering career was soon to come. We will pick up that part of this yarn in a subsequent post.