Ancestry of Pirate Henry Jennings

Would it surprise you to know that pirate Henry Jennings is part of a wealthy family of Bermuda and grandnephew of Perient Trott whose other grandchild, Vice-admiralty Judge Nicholas Trott of South Carolina, tried and hanged Stede Bonnet and other pirates for piracy?

The Jennings are also founding fathers of the modern United States, with connections to the grandfather of President George Washington! 

Presenting the surprising genealogy of Henry Jennings:

The original immigrant to Bermuda was Richard Jennings, his will - as listed in Early Wills of Bermuda: 1629 - 1835 by Clara F. E. Hollis Hallett shows:

Capt. Richard Jennings' purchased - mostly from Capt. William Sayles - the maximum amount of land possible for residents on the tiny island of Bermuda: 250 acres.

Richard Jennings may have plotted to take over the government of Bermuda, yet in three years had become a member of the Bermudan Council. He also sold land there to a “Mr. Carter” in England that, in 1656, belonged to Capt. Lawrence Washington, “High Sheriff of Virginia” and great-grandfather of later U.S. president George Washington. The survey of 1663 includes part of his 250 acres of land (the most allowed in tiny Bermuda) in ten properties:

Capt. Jennings' two sons, Richard II and John inherited that property about 1669: Richard II in Smith's Tribe and John in Southampton Tribe.

Bermuda by J. Blaeu. 1647-49

The pirate Henry Jennings descends from John Jennings and Sarah Richards in Southampton Tribe. As the Early Wills of Bermuda shows:

John's will - written in 1684 and probated in 1688 - and compared to information from his father's will, shows that his brother Richard Jennings II had likely married Mary White, the sister of Anthony White. Richard Jennings II captained Charles Gally, cut logwood at the Bay of Campeche, and lost his vessel to pirate Francis Fernando in 1707. The interesting part is that Henry Jennings was later one of ten Jamaican privateers that included this same Francis Fernando!

In 1700, Richard Jennings II made a call at Charles Town, South Carolina and left this notation about his father's will of 1690, including his mother's remarriage to Robert Hall of Bermuda:

Richard Jennings' Will info from South Carolina Probate Records in 1700

John married a Trott, daughter of Perient and Mary Trott and sister of Perient Trott (brother also of Samuel and Nicholas Trott - the later governor of the Bahamas who traded with pirate Henry Avery). John Jennings' only male child was John.

John Jennings, son of John also appears in Early Wills of Bermuda:

 Here, we first see Henry appear, along with brothers Daniel, Richard, and Benjamin and sisters Mary and Sarah. John made this will in 1733 and died in 1740, so was very much alive when his son Henry had gone to the new town of Kingston in Jamaica:

Christian Lilly's Survey of Kingston, Jamaica in 1703

Henry Jennings had purchased two lots in Kingston. He was listed innocuously in shipping records as a mariner involved in “trade.”

British engineer Christian Lilly made a plan (shown above) of the new town of Kingston which included names of subscribers for town lots. “H Jennings” appears twice: one lot on the east side of Orange Street and another on the lower part of King’s. 

As master of Seaflower in 1710, he collected logwood from the Bay of Campeach – like his cousin Richard Jennings III in Charles Gally - and traded slaves on a minor scale to Jamaica. 

Henry was one of many “sugar drovers,” one who had been recorded losing a sloop Diamond, of four guns, in Jamaica in January 1712.  

Colin Woodard found him in “Bathsheba” of Jamaica in Boston’s customs records on July 7, 1715, just a few weeks before the hurricane that year. 

Henry Jennings in Shipping Records of Jamaica

Henry Jennings in Massachusetts Shipping Records of 1715 - located by Colin Woodard and also shows Henry Timberlake - later taken by Edward "Blackbeard" Thache and Benjamin Hornigold in Delight, late 1716.

In only a few months, perhaps influenced by his “Sea Dog” heroes, Henry Jennings became an American pirate legend. Captain John Balchen, of HMS Diamond, wrote to Admiralty Secretary Burchet from Jamaica on the 13th of May, 1716, describing Henry Jennings’ official commission from “Lord Hamilton… for suppressing of piracys.”  Balchen said Jennings sought to capitalize upon the spilled Spanish treasure, not take pirates. Jennings and Wills, guided by their heroes, greed, and holding little regard for the Spanish even in peacetime, stole recovered treasure directly from their salvage base camp on the Florida shore, rather than simply fishing the wrecks in English waters - the more legal route. Trouble was that most of the treasure was on the La Florida or Spanish coast! Jennings would gather together another fleet to go after – not just wrecks – but foreign vessels that he possibly learned about from the Cuban Deputy-governor del Valle’s letter to Hamilton. 

It seems that hunting foreign treasures was about all the English had the desire to do in the West Indies!

By early 1718, Henry returned to his old home place in Bermuda after his short, blatantly illegal run as a pirate. There, he may have contented himself with the family’s smuggling and slave business. Gov. Bennett, who may have been glad to have him back in local business, wrote to the Board, specifically mentioning “Capt. Henry Jennings one of them (who left off that way of liveing [piracy] some months since) has arrived here who with seven others [who] have surrendred themselves.”

Shortly afterward, a Henry Jennings was found sailing in March 1719 from Jamaica to Philadelphia. The next year, the wealthy maritime warrior operated again as a privateer from Bermuda in the next war with Spain, carrying three prize vessels into New York with cargos of “Snuff, Sugar, Oyle Soap, and European Goods.” In 1723, he was captured by another pirate named “Evans” and held prisoner until a quarrel broke out among the pirate crew. Jennings and other “forced men” retook the ship and sailed it back to Bermuda. The Jennings family operated as merchants, slavers, smugglers, and privateers, making their usual runs to Philadelphia, Jamaica, and New York, yet faded from the shipping records by the 1730s. 

Capt. Richard Jennings III of the Somers Islands and a few other captains named Jennings operated sparsely in Bermudan traffic for the following decades. In 1742, as the aging owner of Henry Jennings & Company of Bermuda, this Henry dabbled in the earliest family business, transporting slaves from Africa to the West Indies in the ironically-named Friendship. While likely pirate and mariner Henry Jennings died before 17th of December 1750, a younger “Capt. Henry Jennings” of sloop Ranger, a vessel owned by “Richard Downing Jennings and Henry Jennings of Bermuda” also traded to Philadelphia in 1767.  

The Jennings’ family businesses of smuggling, piracy, and slavery in America – Johnson’s “Commonwealth of Pyrates” – probably continued right up to the American Revolution and beyond. They may even have shared runs with the smuggling Hancocks of Revolutionary-era Boston. 

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Most of the genealogy is new research of mine, but the latter detailed part was adopted from the 2020 E-edition of Quest for Blackbeard: The True Story of Edward Thache and His World.