When you think of piracy, the Caribbean’s golden age of privateers and the infamous names of Blackbeard, Anne Bonny, and Captain Morgan probably spring to mind. Yet the Pacific Ocean hid its own legion of daring, cut‑throat marauders who ruled the seas with iron fists and glittering treasure. In this roundup we spotlight the 10 brave bloodthirsty pirates who prowled the Far East, each a larger‑than‑life character whose deeds echo through history.
10 Brave Bloodthirsty Pirates Unleashed
10 Lai Choi San
Back in 1956, adventurer‑author Aleko Lilius released I Sailed with Chinese Pirates, a memoir that remains the most vivid source on the legendary female commander Lai Choi San. Lilius claims he earned the trust of this notorious pirate queen and became one of the few Westerners ever allowed aboard her fleet, giving us a rare glimpse into her world.
According to Lilius, Lai Choi San first appeared to him as a Robin‑hood‑type figure of the South China Sea, raiding wealthy merchant vessels and then distributing the spoils among the impoverished coastal communities. He admits, however, that he could not separate fact from the many tall tales that swirled around her name; at first he even doubted her existence until he finally met her in person.
Dubbed the “Queen of the Macau pirates,” Lai Choi San inherited a thriving criminal enterprise from her father, who had secured a semi‑official protectorate from the colonial government in exchange for safeguarding local fishermen from rival gangs. The title of “inspector” bestowed upon her granted official immunity, allowing her to run protection rackets and kidnapping schemes without fear of government retaliation.
Lilius notes that she amassed “barrels of money” from these operations, ruling her crew with an iron fist while demanding ransoms for kidnapped men, women, and children. Though historians debate how much of Lilius’s account is embellished, most agree that Lai Choi San was a formidable force in the South China Sea, wielding both political cover and ruthless ambition.
9 Limahong
Limahong’s fleet cut a swath through the coastal waters of China during the 1570s. Born in Tui‑Chiu, he joined the crew of the pirate Tia‑La Ong as a teenager, quickly rising through the ranks. When Tia‑La Ong fell in battle, Limahong assumed command, inheriting not only the ships but also a delicate relationship with the Ming emperor, who tolerated his raids in exchange for a thin veneer of cooperation.
When the emperor grew impatient with Limahong’s relentless attacks on Chinese villages, a hefty bounty was placed on his head. Seeking fresh opportunities, Limahong seized a Manila‑bound vessel, lured by rumors of untapped riches in the Spanish Philippines, and plotted to establish a new base of operations there.
In November 1574, Limahong led an armada of roughly 74 ships and 2,000 warriors (some accounts inflate those numbers to 200 ships and 10,000 men) into Manila Bay. The first foray was a night‑time test of the city’s defenses, but it quickly devolved into chaos when the camp master’s wife mistook the invading force for angry natives and shouted, “Go away, dogs, or you will all die today!” The miscommunication set the tone for a brutal showdown.
The pirates regrouped, launched a second assault, and set fire to the Spanish camp. In a grisly display, the pirate chief presented the severed ears and nose of the camp master, Martin de Goiti, to his own men. Reinforcements arrived, forcing the pirates to retreat, but Limahong quickly shifted his focus to raiding nearby Spanish settlements, continuing his campaign of terror.
Limahong’s general, who had overseen the first attack, later lied to him, claiming their landing site was too distant for a full assault. The delay allowed Spanish forces to bolster their defenses, and after three days the pirates launched a full‑scale invasion that was finally repelled. Undeterred, Limahong turned his attention to other coastal villages, pillaging wherever he could.
By August 1575, a joint Spanish‑Chinese effort nearly trapped Limahong, but he slipped away, disappearing from the historical record after a final sighting near Guangdong. His legacy endures as a daring, if ultimately elusive, figure who challenged both Chinese and European powers in the Pacific.
8 Shirahama Kenki
Shirahama Kenki began his career as a bona‑fide pirate, but his voyages soon turned exploratory. In 1585, his fleet of five ships made an unexpected appearance off the coast of what the Japanese of the era called Cochinchina—modern‑day Vietnam—where locals initially mistook him for a European trader.
Kenki’s raiding parties quickly targeted villages along the coastline, prompting a response from Nguyen Hoang’s sixth son. The young lord’s forces managed to destroy two of Kenki’s vessels, forcing the pirate to retreat. Yet Kenki was not deterred; sixteen years later he returned, this time under a more diplomatic guise.
When his ship wrecked in a Vietnamese port, the local magistrate, unaware of Kenki’s true identity, treated him as a lawful merchant. The magistrate’s death—whether by accident or design—allowed Kenki to avoid execution. Nguyen Hoang, recognizing the potential benefits of a sanctioned trade route, wrote to the Tokugawa shogun, praising Kenki’s handling of the incident and paving the way for the issuance of “red‑seal” permits that legitimized Japanese‑run commerce in the region.
7 Eli Boggs
Eli Boggs, an American who turned pirate in the bustling harbor of Hong Kong, earned a reputation as a strikingly handsome criminal with “lily‑white” hands and a delicate, almost feminine demeanor. Despite his appearance, he proved as ruthless as he was good‑looking, eventually being captured and tried for piracy and murder.
During his trial, Boggs claimed he was a pawn in a larger conspiracy orchestrated by the notorious gangster Wong Ma‑Chow, who allegedly acted under the direction of Daniel Richard Francis Caldwell—the British Secretary for Chinese Affairs in the 1850s. Caldwell, a former merchant turned colonial official, allegedly leveraged his extensive network of informants to both suppress piracy and control the region’s vice‑laden brothels.
Boggs delivered a two‑hour, eloquent testimony that accused Caldwell of using his official position to shield his own criminal enterprises, including the licensing and ownership of brothels. The accusations sparked what became known as the “Caldwell Affair,” a scandal that exposed deep corruption within the colonial administration and cemented Hong Kong’s reputation as a hotbed of vice.
Although the court convicted Boggs of piracy, the lack of concrete evidence linking him to murder meant he escaped a death sentence. Instead, he was deported from Hong Kong, his fate a cautionary tale of how a seemingly genteel pirate could become entangled in a web of colonial intrigue.
6 William Henry Hayes
Born in Cleveland, Ohio, around 1829, William “Bully” Hayes earned his moniker through a life of relentless ambition and scandal. After mastering sailing on the Great Lakes, he ventured into the Pacific, first appearing in Australian records in 1857, where his reputation as a cunning swindler quickly spread.
Hayes built a criminal empire by convincing ship owners and captains to sign over their vessels in exchange for a promised share of cargo—promises he never intended to keep. His personal life was equally tumultuous; he married Amelia Littleton and later Rosa Buckingham, the latter meeting a tragic end alongside her child, brother, and servant. In 1860, he faced charges of indecent assault and spent time “blackbirding,” luring unsuspecting individuals into forced labor under false pretenses.
By 1874, Hayes reportedly accumulated five additional wives, a testament to his unbridled hedonism. Growing public outrage over his violent exploits forced him to abandon his trading post in the Caroline Islands. He escaped on a whaling ship to San Francisco, where he once again commandeered a vessel—this time with another man’s wife aboard—for what would become his final voyage.
Hayes’ ultimate fate remains shrouded in mystery; most accounts agree he met his end in a violent altercation with a fellow sailor, his body tossed overboard without ever facing formal conviction. The blend of fact and fiction surrounding his life makes him one of the Pacific’s most enigmatic and brutal characters.
5 Shap‑Ng‑Tsai
Shap‑Ng‑Tsai began his criminal career as a smuggler in the chaotic aftermath of the First Opium War. With Hong Kong officially a British colony after 1842, the new trade treaties made smuggling more lucrative than legitimate commerce, prompting many illicit traders to adopt pirate tactics.
From his base in what is now Dianbai, Shap‑Ng‑Tsai launched a protection racket, offering to escort and safeguard smugglers for a fee. By 1849 his fleet had swelled to an astonishing 70 vessels, stretching from China’s coast down to Vietnam. While this operation initially escaped serious scrutiny, the fleet’s attacks on British and American merchant ships—protected under newly signed treaties—prompted a swift response from the Royal Navy.
Shap‑Ng‑Tsai proved a master of deception. When the Royal Navy moved to seize his seized ships, he cleverly allowed his captured vessels—roughly 100 in number—to be auctioned back to him, then tacked the purchase price onto his ransom demands. In October 1849, a decisive naval battle destroyed 58 of his ships, including his flagship, and claimed about 1,700 of his crew’s lives. Yet the crafty pirate escaped, later being bought out by the Chinese government and re‑appointed as a respectable naval officer.
4 Wang Zhi
Wang Zhi started his career as a salt merchant during the Ming dynasty, a period when the government imposed heavy taxes on the lucrative salt trade. Frustrated by the fiscal burden and the constant harassment from coastal pirates, Wang sought protection by hiring Japanese pirates, eventually forming his own seafaring syndicate that blended commerce with outright piracy.
His operation grew to encompass the transport of European firearms—handguns and cannons—into Asian markets, while simultaneously exporting gunpowder and its essential ingredients. This trade made him a vital conduit between Portuguese merchants and the East, and he even encouraged the spread of Christianity, believing that missionary activity could bring technological advantages.
Wang’s ambitions, however, clashed with the Tokugawa shogunate’s growing suspicion of foreign influence. In 1559, the shogunate cracked down on his activities, leading to his execution. His downfall illustrates how the line between legitimate trade and piracy could blur, especially when political and religious currents intersected.
3 Cai Qian
Cai Qian’s piratical career was brief yet ferocious. Originating as a humble peasant‑turned‑fisherman, he joined a pirate crew in 1795 and quickly rose through the ranks, employing ruthless tactics—including using his own wife as bait—to eliminate rivals and secure his own command.
By 1800, provincial authorities took notice after a heavily armed ship under his control was captured. Interestingly, Cai’s crew operated without a formal hierarchy; there were no official captains or titles, a structure that initially confused officials and bought him precious time before a concerted crackdown began.
When a massive typhoon in 1800 destroyed many vessels from rival fleets, the remaining pirate bands coalesced under Cai’s banner, and he boldly declared himself the “King to Pacify the Oceans” in 1806. His growing power alarmed the Qing government, which launched a campaign of smaller, targeted vessels to cut off his supply lines. The strategy succeeded, and in 1809 government forces finally cornered and killed Cai at sea.
2 Charlotte Badger
Charlotte Badger was born in Worcestershire, England, and baptized on July 31, 1778. In 1801 she was transported to Sydney after being convicted of breaking into a house, receiving a seven‑year sentence. Two years shy of completing her term, she and a fellow convict were assigned as servants to a settler family bound for Tasmania.
During the voyage, a mutiny erupted among the convicts. Badger emerged as a pivotal figure—some accounts credit her with rallying the rebels, whipping the ship’s captain, and leading a daring raid on another vessel to seize weapons and supplies. Together with her ally Catherine Hagerty, she escaped with a fellow convict and the ship’s first mate, commandeering a vessel loaded with provisions sufficient to establish a new settlement.
The mutineers set up a makeshift colony at Rangihoua Bay in New Zealand, but the group soon fragmented. Some, including the first mate, returned to Europe, while Hagerty died. Badger remained among the Maori, integrating into their community. Later rumors suggest she either perished there, was kidnapped, or managed to reach the United States, but the exact details of her final years remain shrouded in mystery.
1 Cheng Ch’i And Ching Shih
When Cheng Ch’i’s pirates seized a brothel, he chose one of the courtesans to become his wife, forging a partnership that would blossom into one of the most formidable pirate empires in history. The union produced a powerful fleet under the command of the former prostitute, Ching Shih, who would later be known as Cheng I Sao.
For six years Cheng Ch’i and Ching Shih ruled the South China Sea together, until a devastating typhoon claimed Cheng’s life. Ching Shih immediately assumed command, promoting the 21‑year‑old Chang Pao—her late husband’s protégé and former lover—to the rank of lieutenant. Under her iron‑fisted leadership, the fleet grew to an astonishing 1,600 ships and over 70,000 pirates, spies, and agents.
Ching Shih imposed a strict code of conduct: her crew could not plunder villages that had provided them with food or aid, and any act of rape was punishable by death. Pirates wishing to keep a captive woman had to marry her and treat her respectfully, with infidelity leading to execution. In return for unwavering loyalty, she ensured her sailors were well‑armed, well‑supplied, and even provided a rudimentary pension system.
Eventually Ching Shih negotiated an amnesty with the Chinese authorities. While the precise terms remain debated, one popular story claims she avoided direct humiliation by marrying Chang Pao, who then performed the official ceremony, satisfying the governor’s requirement without compromising her dignity. After retiring, she either ran a smuggling operation, a brothel, or both, and lived to the ripe age of 69, a remarkable longevity for a pirate of her era.