Pirates attacked a city. In 1668, 500 pirates gathered to raid Portobelo, a Panamanian port where Spain shipped supplies back to its homeland. Even Portobelo, the most heavily fortified of Spain's colonies at the time, could not repel pirates striking simultaneously from sea and land. Three years later, Panama City met the same fate. A fleet of 36 ships and 1,200 pirates poured in from both sea and land at once, reducing Panama City to ruins. This was the work of Henry Morgan, the "Buccaneer King."
The reason for attacking on land was clear. Privateering at sea required handing over 10% of the plunder to the government, along with shares for those who lent ships or invested. Plundering on land carried no such obligations, because it was not covered by contract. When launching an attack, Morgan persuaded pirates uneasy about their small numbers by arguing that fewer men meant bigger shares. His ruthless strategies were astonishing. He seized priests and nuns from churches and used them as human shields to assault fortresses — a tactic Spain, a Catholic nation, could not possibly counter.
When Spain protested fiercely against the Panama raid, Morgan was summoned to the British royal court in 1672 for investigation and awaited punishment. But Charles II, impressed by his extraordinary exploits, instead knighted Morgan and appointed him Lieutenant Governor of Jamaica. Sir Morgan received a royal mandate to crack down on pirates and forced them to abandon their activities or stay away from Jamaica. Drawing on his pirate experience, he developed Port Royal into the wealthiest port in the world.
Morgan did not squander the money he earned through plunder. He ran three sugarcane plantations and invested in the high-demand sugar business and real estate. Successful in every venture he took on — as a pirate, politician, and businessman alike — he enjoyed wealth and fame until his death in 1688 at age 53. His estate was worth roughly 28 billion won. Did the sea god grow angry at his overly prosperous life? In 1692, the Jamaica earthquake swallowed his grave along with all of Port Royal. Some 250 years later, Morgan was reborn as a famous Jamaican rum brand: Captain Morgan.
Henry Morgan's disruptive leadership resembles Elon Musk's "game-changing" management style. Just as pirates from the sea toppled city fortresses, Musk has completely shattered the framework of existing industries through bold challenges. While the world's automakers remained locked in competition over internal combustion technology, he boldly mass-produced Tesla to seize the lead in the electric vehicle market. He also stunned the world in the space business, long monopolized by governments, with SpaceX and Starlink.
Their leadership styles — presenting daring visions, providing powerful motivation, and drawing full participation — are also similar. When Morgan called on his men to march "beyond the sea to the land" and attack the enemy nation, Spain, he was treating them not as petty pirates but as warriors bringing down an empire. Musk, too, has emphasized that "colonizing Mars" is not merely a corporate goal but the future of humanity. He instills pride in his employees, framing them not as mere salary earners but as agents participating in a historic event.
Overwhelming achievements secure the government's trust. Just as a pirate became a nobleman and rose to lieutenant governor, Musk, backed by U.S. President Donald Trump, was tapped to head the Department of Government Efficiency (DOGE). Although he stepped down early after drawing criticism for harsh remarks, he developed a taste for political engagement. Musk's business scope is no joke either. Beyond automobiles and space, his ventures span satellite communications, artificial intelligence (AI), social media, underground tunnels, brain-computer interfaces, and solar power. How far can he demonstrate his "endgame" prowess?
"Disruptive innovation" requires disruptive leadership. Morgan transformed "destructive" pirates into "disruptive" ones. From Britain's perspective, he was the foremost contributor to dismantling the Spanish-dominated order of the Caribbean and reshaping Britain into "the empire on which the sun never sets." The order Musk is reshaping in electric vehicles and space is likewise upending the rules of the game. Don't destroy the game, just disrupt it.
