[10][11][12][13][14][15][16] Although little is known of Jennings's early life, he was first recorded as a privateer during the 1701–1714 War of the Spanish Succession operating from Jamaica, then governed by Lord Archibald Hamilton.

[18] News of the wreck and their distress call reached Jamaica in November 1715, and Jennings and his ship Bersheba sailed immediately to the Florida coast.

They had been sanctioned to "Execute all manner of Acts of Hostility against pyrates according to the Law of Arms," with explicit instructions not to attack anyone except pirates.

[3] The nucleus of the pirate force was a group of English ex-privateers: Jennings, Charles Vane (on the Bersheba), Samuel Bellamy, Benjamin Hornigold,[citation needed] and Edward England.

[22] When Jennings and his men raided the storehouses,[4] they forced the retreat[3] of around 60 soldiers[3][21] with superior numbers of 300 privateers,[21] stealing about £87,500 in gold and silver, equivalent to a ten-year salary.

[clarification needed][23] According to Connor, shortly after arriving in Nassau, Jennings took a small Spanish trading sloop from Hornigold.

[24] Jennings set sail for Jamaica carrying back an estimated 350,000 peso,[3] or 120,000 pieces of eight,[18] accompanied by fellow Captain John Wills and his crew of the Eagle.

The Spanish captain followed Jennings's fleet back to Jamaica,[25] and following it up the Cuban shore through Windward Passage and to the mouth of Port Royal Harbor.

As a result, the viceroy, who had also heard of Jennings's pillaging the shore camp, was "outraged," and contacted Hamilton to demand the pirates be hanged.

With Hamilton stating he knew nothing of such pirates and there must have been a mistake, said he would, in turn, flog any Spanish he could find in Jamaica if the threat to English lives was carried out.

However, Hamilton complained to the local merchants about possible conflict with the Spanish over the pirates, who in turn advised Jennings to quietly leave Jamaica.

[25] Shortly after leaving Jamaica, Jennings and his men overtook and plundered a Jamaican merchant vessel of Englishmen, stripping valuables down to the captain's clothing.

Two others, Samuel Liddell of the Cocoa Nut and James Carnegie of the Discovery, joined with their small sloops without commission, accepting Jennings’s overall command.

[1] When Jennings sailed with the Bersheba to the wrecks this third time, he was under direct orders of Daniel De Costa Alvarenga, a Jewish merchant from Kingston who was the new owner of the sloop.

The two pirate captains and their crews abandoned ship upon the sight of Jennings's four sloops British colors, fleeing sailing canoes.

[24] A sailing canoe later approached the St. Marie to trade while the crew was dividing spoils, and Jennings's then "inflicted punishments" on the new captives to locate their larger vessel.

[1] After the raid on the Marianne, Jennings, Ashworth, and another captain set sail for New Providence, an island in the Bahamas and former capital of the collapsed Bahamian government.

[1] According to a deposition based on an eyewitness, when Jennings arrived in Providence he "bought in as prize a French ship [Marianne] mounted with 32 guns which he had taken at the Bay of Hounds [Bahia Honda], and there shared the cargo (which was very rich consisting of European goods for the Spanish trade) amongst his men, and then went in the said ship to the [Florida wrecks] where he served as Commodore and guardship.

[25] After political pressure, Hamilton issued proclamations in April 1716 forbidding all commissioned vessels in Jamaica from fishing the Florida wrecks for plunder.

[18] It was one of his last acts as governor before Hamilton was himself arrested, and overall he declared all passes issued to treasure hunters null and void, meaning that henceforth, any captain attacking Spanish forts or vessels in peacetime was a pirate.

[26] Declared a pirate by Lord Archibald Hamilton,[26] Jennings could not return to Jamaica, and so he established Nassau as his base for further raids on Spanish wrecks.

[1] Hamilton was arrested in October 1716 for the crime of violating treaties with the Spaniards,[18] and he left Jamaica on about 22 September to England, accompanied by a fleet of seventeen ships.

[1] The newly appointed Governor of the Bahamas, Woodes Rogers,[30] issued a royal decree on 5 September 1717, which pardoned all pirates who surrendered within the year.

[4] He was one of 400 pirates who took advantage of the amnesty,[25] and, after serving as a privateer in the War of the Quadruple Alliance,[29] retired to Bermuda to live the rest of his life "as a wealthy, respected member of society.

The Pennsylvania Gazette of July 4, 1745, reported: "They had advice in Bermuda of the loss of 7 of their sloops ... taken in different parts of the West-Indies within a few months past, commanded by the following Captains, viz., Henry Jennings, ..."[2][32]