Rosetown Review: The ‘legalized’ pirates of the Upper Houses

by Richard Franklin Donohue

Town Historian

“You may, by Force of Arms, attack, subdue, and take all Ships and other Vessels belonging to the Inhabitants of Great Britain, on the High Seas, or between high-water and low-water Marks, except Ships and Vessels bringing Persons who intend to settle and reside in the United Colonies, or bringing Arms, Ammunition or Warlike Stores to the said colonies, for the Use of such inhabitants thereof as are Friends to the American Cause.”

From instructions to the commanders of private ships or vessels of war, April 3, 1776.

In the years leading up to the American Revolution the people of the Middletown Upper Houses became increasingly involved in a burgeoning but under-documented coastal trade operating out of the village. Like many merchants along the Connecticut River, these maritime businessmen owned and sometimes operated vessels that sailed to and from the West Indies and along the Eastern seaboard, trading local produce for molasses and rum, the most lucrative products of the sugar cane grown by enslaved workers on the Caribbean plantations.

After the Revolution, John Smith built a new wharf and store near South Street and prospered in the new maritime economy of the Upper Houses. He died suddenly in 1786 and is buried in the Old Burying Ground along with his first wife, Lucy, and their son Joseph, who died at sea. (submitted)

In the 1740s, local sailors served on vessels out of Middletown and Haddam bound for Barbados and London and the first wharves and warehouses were erected near South Street. Local ship construction began by 1759 with a “building yard” located along Wall Street.

In the 1770s, several of the village’s residents had been living very well off the West Indian trade for quite a while. As the decade and its attendant politics progressed, however, many of these merchants and sea captains found themselves needing to diversify their income.

In February of 1776, Americans learned that Parliament had passed the Prohibitory Act that ended all trade between Britain and the colonies, allowed for the seizure of any vessel trading with the colonies, and effectively set up a blockade of the American coast.

While many of the colonies had previously petitioned the Continental Congress to allow the fitting out of vessels as privateers, conciliatory hopes had thus far prevented the majority of the body’s delegates from embracing such drastic measures. This new “dismemberment of the British Empire,” as John Adams called the act, “altered the minds” of many in the Congress who now felt, like Connecticut’s Oliver Wolcott, that the time had come “to take care of ourselves.”

Several privateersmen from the Upper Houses who were captured were sent to the British Prison Ship Jersey in New York. At any given time, more than 1,000 Patriot prisoners were held in abysmal conditions in this retired warship designed to hold 400 men. (Image retreived from the Library of Congress.)

At the end of March, Congress adopted a resolution authorizing the use of privateers “to provide for their defense and security.” After obtaining financial bonding to ensure the proper conduct of their crew and acquiring commission papers, or “letters of mark,” privateers were allowed to capture a British vessel along with its cargo and then bring the prize “to some convenient port or ports of the United Colonies” so that a maritime court could determine the catch’s validity.

Once the vessel and cargo were determined to be a lawful catch, they could be sold and the earnings divided amongst the privateer’s owners, captain and crew.

Just a few days before Congress passed its answer to the Prohibitory Act the British were chased out of Boston after being contained within the city by George Washington and his army for 11 months. British commander General Howe reorganized his forces and set his sights on New York with the idea of separating New England from the rest of the colonies.

In April of 1776, the Continental Congress, having adopted the use of privateers as a way to protect the colonies’ shipping interests from the British, issued instructions to those who would join the “militia of the sea.” (Image retrieved from the Library of Congress)

Prison Ship Jersey

On June 29, 45 British vessels entered New York harbor and brought the blockade of the American coast into Long Island Sound. Connecticut’s merchant vessels were suddenly faced with the choice of losing everything or finding a new way to replace their lost income.

Brothers John and Joseph Smith were the grandsons of the Rev. Joseph Smith, first settled pastor in the Upper Houses. Both men received a healthy inheritance when their father died in 1768 that they likely invested in the village’s emerging maritime trade.

When the war for independence came, both men were married, each with six children, and therefore had a great deal to be concerned about as they watched their maritime interests slowly deteriorate.

In July of 1779, Joseph teamed up with Ebenezer Sage & Co. as a bonder and captain of the 10-gun sloop Dolphin. Smith acquired a letter of marque for a cruise to the island of Hispaniola (now the Dominican Republic and Haiti) and sailed in November.

The following year he invested in another privateer owned by Comfort Sage, the 10-gun schooner Bunker Hill. Among the crew of 45 was Joseph’s brother John, serving as lieutenant. During a “spirited engagement” on April 14, 1780, John took command of the Bunker Hill after her captain was wounded and is thus credited with capturing the British privateer sloop Dolphin along with her cargo of “100 poncheons of rum.”

A puncheon, or puncheon, cask holds on average 100 gallons of liquid, not a bad prize indeed.

In 1781, John Smith was the owner of the privateer schooner Weasel, commissioned on Oct. 15 with Sanford Thompson as captain and Jacob White of the Upper Houses as mate. No cruise records exist for this vessel until the following February when the Weasel captured the British sloop Sally near Oyster Bay, L.I., with her “cargo of British goods.”

Meanwhile, Joseph Smith spent most of the year as captain of two different privateers, the schooner Chatham in January and later the brigantine Lady Green, which had a crew of 80 men and mounted 14 carriage guns.

While sailing off Montauk Point in December the Lady Green captured the British brig Unity loaded with Jamaican rum and bound for New York. When the Unity and her crew were brought to New London’s maritime court for processing, it was discovered that two members of the crew were actually Americans previously captured by the British and pressed into service.

While the Smith brothers were very active in the business of privateering the most successful privateer captain in the Upper Houses was without a doubt Nathan Sage. Between 1779 and 1781 Sage captured more than a dozen British vessels, including the brig Ranger with a hold full of gun powder and the brig Resolution, “laden with rice and turpentine,”

After completing two bountiful voyages with his 18-gun ship Hunter, Sage sold the vessel to John Smith in April of 1782, who promptly set out on a cruise with a crew of 100 men. No record exists of the vessel’s activities during the expedition.

At least 24 men from the Upper Houses served on privateers during the American Revolution, but not all with favorable results. The British made no distinction between these “legalized pirates”(as they are often called) and actual pirates and gave them little quarter when captured.

By the end of the war, 16 Upper Houses privateer crewmen had been captured by British vessels and sent to the prison ship Jersey in Wallabout Bay, N.Y. At least four – Samuel Smith, Nathaniel Stocking, Samuel Stow and Ebenezer Sage– died while imprisoned aboard this “Hell afloat.”

In April of 1782 the 16-gun brigantine General Green set sail from Wethersfield with 100 men including four from the Upper Houses: John Barns, Comfort Ranney, Joseph Ranney and James White. While cruising 45 miles south-southeast of Nantucket, the privateer met up with the British ship of war Virginia and was captured.

The vessel was taken to New York and 83 members of the crew were sent to prison ships in the harbor. Many, including James White, did not survive.

Privateering played an important part in the success of the American Revolution. Through this ancient practice, ambitious patriots could simultaneously serve the cause of freedom and seek their personal fortunes. 

For those men who went forward as privateers from the Middletown Upper Houses it also allowed them to develop the economy that would ultimately define their community’s existence as a riverport for the next 30 years.

As the nation commemorates the semiquincentennial of both its Declaration of Independence and the subsequent war to obtain it, we are encouraged to reflect on the ways that our modern lives and ideals connect us with the generation that set it all in motion 250 years ago. This flotilla of intrepid sailors gives the people of this once and future riverport town our distinctive claim to the American Revolution. CL

For more on Nathan Sage see “Nathan Sage: A Gentlemen Sailor With a Mind To Make His Fortune,” Rosetown Review in the March 2021 edition, available online through the Cromwell LIFE archive.