|This article needs additional citations for verification. (November 2010) (Learn how and when to remove this template message)|
Although little is known of Jennings' early life, he was first recorded as a privateer during the War of the Spanish Succession operating from Jamaica, then governed by Lord Archibald Hamilton. There is evidence that Jennings owned enough land in Jamaica to live comfortably, thus leaving his motivations for piracy to conjecture.
His first recorded act of piracy took place in early 1716 when, with three vessels and 150-300 men, Jennings' fleet ambushed the Spanish salvage camp from the 1715 Treasure Fleet. After forcing the retreat of around 60 soldiers, Jennings set sail for Jamaica carrying back an estimated 350,000 pesos.
While en route to Jamaica, Jennings encountered another Spanish ship and captured another 60,000 pesos.
When Jennings encountered "Black Sam" Bellamy, he teamed with him to commit more piracies against the French. When Bellamy double-crossed him, Jennings' ruthlessness was evidenced in the brutal slaying of more than 20 Frenchmen and Englishmen, and the burning of an innocent Englishman's merchant sloop.
Jennings was declared a pirate by the very governor who had commissioned him and originally condoned his actions (taking a cut for himself). Jennings was forced to flee from Jamaica and eventually established a new base of operations in New Providence in the Bahamas. Based out of Nassau for a time, Jennings became an unofficial mayor of the growing pirate colony and retired from piracy.
In early 1718, Jennings surrendered to authorities following the general amnesty declared by the newly appointed Governor of the Bahamas, Woodes Rogers. He retired as a wealthy plantation owner in Bermuda, where he received his pardon.
He is one of very few pirates said to have enjoyed a successful retirement. It is unknown what his ultimate fate was, though some historians speculate that he was captured by the Spanish in his later years, dying in obscurity in a New Spain prison. Other legends have him growing old with his family in Bermuda.
- Captain Charles Johnson; David Cordingly, General history of the robberies and murders of the most notorious pyrates. page 9