In July 1715, Spain's Treasure Fleet, sailing home loaded with plundered riches, was struck by a hurricane off the coast of Florida. Ten of the 11 ships sank, leaving only one afloat. Hearing rumors that the Spanish navy was conducting a salvage operation to recover the treasure—worth more than 20 trillion won at today's value—Henry Jennings was the first to act. Jennings raided the salvage base guarded by some 60 Spanish sailors, secured an immediate surrender, and returned with spoils worth roughly 30 billion won.
Operating a privateer at the time, Jennings was remarkably well-informed. He likely learned of the Treasure Fleet's sinking from the Governor of Jamaica, or by intercepting a Spanish fleet liaison vessel. Jennings also wielded considerable influence in mobilizing pirates. He swiftly assembled three pirate ships and around 200 pirates. He was fair in distributing the spoils as well. Despite being the first joint operation of its kind, the participating pirates raised few complaints about how the loot was divided.
As major pirates such as Benjamin Hornigold, Edward Teach, and Charles Vane joined Jennings's operation, the pirates of the Caribbean began consolidating forces and embarking on bold acts of piracy. This was the "Flying Gang," which carried out joint operations. As more pirates flocked to him, Jennings, together with Hornigold, established the "Republic of Pirates" in Nassau, the Bahamas, and led the republic following Hornigold and Samuel Bellamy.
Drawing intelligence and favors through backdoor dealings with the Governor of Jamaica, Jennings developed a greater taste for piracy than for privateering and steadily expanded his power. His sharp intelligence and political backing surely played a role. When King George I of Britain issued a pardon to pirates in 1718, Jennings shrewdly retired from piracy and had his fortune recognized. He settled on the island of Bermuda, far from Jamaica, where he is believed to have lived out a comfortable life as a wealthy plantation owner.
Henry Jennings's shrewd piracy resembles the sharp-eyed management of Microsoft's Bill Gates. In 1980, when Gates heard that IBM was entering the PC business and looking for an operating system (OS), he acquired the rights to "86-DOS" and supplied it to IBM. He had nimbly snatched up a treasure that someone else had painstakingly secured. Moreover, rather than selling MS-DOS (Microsoft Disk Operating System) outright, Gates structured the contract as a licensing deal—instantly catapulting Microsoft into the world's largest software company.
Gates, too, was surrounded by his share of "major pirates." Beyond Microsoft co-founders such as Paul Allen and Steve Ballmer, rivals like Apple's Steve Jobs, Oracle's Larry Ellison, and Dell Technologies' Michael Dell collaborated closely and competed fiercely for dominance in Silicon Valley. They were the "Digital Pirates" of the dawning "Digital Gold Rush" era.
What pardon did he seek? In his prime, Gates earned money so relentlessly that he was nicknamed the "Demon of Silicon Valley," and after his success, he saw his global reputation tarnished by various affairs and scandals. Gates announced his retirement in 2008 and devoted himself to philanthropy. He poured himself into charitable work with such intensity that one might wonder whether he had earned money like a demon precisely so he could give it away. As of 2025, his donations total an astonishing 100 billion dollars—more than 140 trillion won.
Are opportunities equal for everyone? Henry Jennings became a pirate captain who ruled the Caribbean through a joint operation to plunder the Treasure Fleet, and Bill Gates, with no technology of his own, sold MS-DOS to become a global software powerhouse. Gates said (or is said to have said): "Flipping burgers is not beneath your dignity. Your Grandparents had a different word for burger flipping, they called it opportunity."
