Henry Jennings was an educated ship captain with an estate in Bermuda, and he decided to become a privateer in the service of the Great Britain. He fought as a privateer during the War of the Spanish Succession, operating from Jamaica and attacking Spanish Navy vessels. In July 1715, Jennings and his men, sailing aboard the Bersheba, plundered several Spanish treasure fleet ships that had been wrecked by a hurricane off the coast of Florida, seizing one of the richest prizes in pirate history. In early 1716, he ambushed a Spanish salvage camp in Palma de Ayz, Florida to recover salvaged gold from the treasure fleet, and he was forced to head for Nassau in the Bahamas, having abandoned privateering in favor of piracy. He began to prey on British ships off Jamaica in 1716, and he also raided French Navy ships such as the large armed merchant ship St. Marie and the two ships sent to recover her. Jennings collaborated with Samuel Bellamy, Benjamin Hornigold, and other pirates, but Bellamy and Hornigold betrayed him and stole a large portion of his loot. In 1716, he became a governor of the Republic of Pirates, and he decided to take the King's pardon in 1718, allowing for him to retire with his ill-gotten gains.