For a long time, Hong Kong has consistently ranked as one of the safest cities in the world. It can be difficult to imagine the days when these same peaceful streets were so roiled by violence that leaving home at night without a pistol — or even venturing beyond town limits in broad daylight — was inviting danger.
In the words of a lieutenant-colonel in the King’s Dragoon Guards, Hong Kong was in those days “the fearfullest hole in the world,” a Wild East frontier town in which death always lurked around the next promontory. On top of that, it was also a huge commercial disappointment.
That’s because of piracy, according to preeminent missionary and official government interpreter Karl Gützlaff, who out its threat to shipping as the most important reason for Hong Kong’s failure to take off in its early days as a British colony. With a touch more drama, American writer Gene Gleason pronounced it one of the “four horsemen” that terrorised the young colony, together with typhoons, epidemics and fires.
The days of piratical royalty like Cheng I Sao and Cheung Po Tsai may have been long gone, but a new generation of minor-league marauders was beginning to reave and sack, and carve their names in blood and song. Shap Ng Tsai (Sap6 Ng5 Zai2 十五仔) and Chui A-poo (Ceoi4 Ngaa3 Bou2 徐亞保), with their fleets harboured west and east of Hong Kong respectively, were the biggest buccaneers to follow in the wake of Cheng’s pirate federation.
Chui set sail from Hong Kong in 1849 with a 500-pound bounty on his head after killing two British officers for harassing a local girl, at least according to local lore. As the public learned about the incident, pressure mounted on the admiralty to avenge their deaths and bring Chui to justice. A punitive expedition led by two Royal Navy gunboats and a commercial steamer set a course for Mirs Bay when summer rolled around. They found Chui’s band of 27 war junks just off Tysami in the bay’s upper reaches, which they had just ransacked and put to the torch.
As the flames licked the water’s edge and the village went up in smoke, the thunderous sound of His Majesty’s brig Columbine’s cannons heralded the start of the Battle of Tysami. Chui’s fleet scattered as they fell under heavy fire and beat a hasty retreat for their base at Bias Bay. They made it back to their home waters but were bottled up by the British, who regrouped and set their sights on Chui’s base, leaving the pirate haven in ruins.
Just as soon as the ships returned to port victorious, they were dispatched again to deal with Shap, whose racket ran from the Pearl River Estuary all the way to Vietnam. Accompanied by eight Qing navy junks, the Columbine, Phlegethon and Fury engaged Shap in a weeks-long chase westwards to the uncharted islands and channels off Haiphong. Shap reckoned they had found safety in Vietnam’s inland waters after they cleared the sandbar guarding the mouth of the Tonkin River, but he was sadly mistaken.
The British commander of the battle, John Charles Dalrymple Hay, stormed over the sandbar at high tide with cannons blazing. The pirates scarcely had time to weigh anchor, with the strong river current keeping them from bringing their guns to bear on the British. Three days later, 58 of the pirates’ 64 junks were resting on the river bed. Qing admiral Huang Haiguang, forced to sail with the British when his junks couldn’t keep pace, is said to have leapt overboard and swum to a pirate junk, taking it single-handedly in an effort to keep up his end of the bargain.
Like Cheung Po Tsai, Shap surrendered in exchange for a posting in the Qing navy, fated to be vanquished by Hay once again in the Second Opium War.
Britain secured the right to chase pirates anywhere in Chinese waters after the war, and pirate-hunting became a sport for the seamen of the China Station. Bounties offered by the admiralty for captured pirates even had to be rescinded, because they were depleting the treasury and resulted in the killing of innocents by overzealous sailors.
The next worthy adversary for the men of the Royal Navy was neither a upstart Cantonese Robin Hood nor the progeny of a storied rebel king: he was an American outlaw named Eli Boggs. After raiding opium clippers for the better part of a decade, Boggs’ downfall came, appropriately, on 4 July 1857. The bounty on his head was claimed by a fellow American sailing with the Royal Navy, Captain Bully Hayes, a decidedly unheroic figure who achieved notoriety for blackbirding (a kind of maritime kidnapping) islanders in the South Seas.
Boggs’ trial became the talk of the town. By various accounts, the black-hearted desperado said to have had a captive dismembered as a warning to others was “almost tenderly good-looking” and had a “striking feminine appearance, large lustrous eyes, flashing smile and delicately white hands.” Although he was sentenced to transportation for life, Boggs would never see the penal colonies: he was released on health grounds after one year in jail and subsequently disappeared not just from the colony but from the public record entirely.
Despite these thrilling exploits, it was the march of technology more than soldiers that killed old school piracy. Ironclad steamships, riding high in the water and cutting through the waves in any weather, were in a league of their own. No longer could a small fleet of fishing lorchas — a hybrid Chinese-Portuguese junk often used by pirates — claim overwhelming advantage after a sailing ship becalmed in coastal waters.

Attack on, and Destruction of, Part of the Pirate Squadron of Shap-ng-tsai, in the Gulf of Tonkin on the 21st of October, 1849, with Columbine, Fury and Armed Steam Vessel Phlegethon – National Maritime Museum, Greenwich, London
Instead of openly confronting their targets in the open ocean, pirates henceforth developed a strikingly modern strategy: hijacking. They would mingle with ordinary passengers before rushing the deck, murdering the crew members who put up a fight and seizing control of the vessel. Commandeered ships were typically steered to some secluded and sympathetic haven on the coast where they could rendezvous with pirate junks and hand over valuables from the hold and passengers’ pockets before sending the steamer to limp back into port. A few wealthy passengers might also retained for ransom payments.
The most infamous hijacking that took place in this period was that of the SS Namoa in 1890, a steamer drawing toward the Chinese coast from Singapore. Outcry throughout the colony was amplified by the harsh treatment of European passengers on the Namoa, who were crammed into the saloon in scenes likened to the infamous Black Hole of Calcutta.
It had been unthinkable that a large steamship under the protection of the British Empire could be taken by pirates, but now people’s eyes were opened wide to the new threat of hijackings at sea. Thereafter, steamers for other China ports went to sea with their superstructures fortified with steel grilles and barbed wire, machine guns mounted on their bridges and passengers locked in their cabins. Most of the pirates involved were also eventually arrested and tried – and unlike Boggs, they would be given no quarter. They were publicly beheaded on the beach near the Kowloon Walled City by Qing officials.
But neither the pirates’ harsh punishment nor these precautionary measures could deter future attacks. Piracy continued to flourish along the South China coast with 51 major cases taking place in the interwar years. The most devastating of these came in 1914 when the SS Tai On was burnt to the water’s edge by pirates thwarted by the stout resistance put up the ship’s crew. Over 200 lives were lost in the blaze.
Piracy loves a vacuum, and has always thrived at in times of political instability, from the Ming-Qing transition in the mid-17th century to the mid-19th century Taiping Civil War and the Xinhai Revolution in 1911. For this reason, the late 1920s saw the last great hurrah for cutthroats and corsairs of Canton, as Kuomintang leader Chiang Kai-shek fought his way north to quash the Nationalists’ warlord rivals and reunite China.
A repeat of the Tai On tragedy nearly occurred in 1926 when the officers aboard the Suning successfully retook the ship from pirates who then set the ship on fire. In another deft move, the captain turned the ship to windward and smoked out the pirates. The 1929 attempt on the Haiching unfolded in a similar manner, with pirates disguised as passengers unsuccessfully trying to commandeer the ship as it passed by Bias Bay. The Haiching’s officers not only fought off the pirates but soon defeated them and put out a fire they started.
The following year, British submarines sank a hijacked steamship belonging to a state-owned Chinese company as it plied China’s territorial waters at Bias Bay. The incident not only had political repercussions but also led to the death of innocent passengers and crew who went down with the ship, in spite of the navy’s attempts to rescue all those onboard.
There was nothing glamorous about these hijackings. It had been decades since the public had the chance to swoon over a dashing anti-hero like Eli Boggs. But the sensational memoir I Sailed With Chinese Pirates, published by journalist and adventurer Aleko Lilius in 1931, soon reignited the public’s age-old fascination with pirates.
Lilius’ volume claimed to be an account of the time he spent in the fleet of a mysterious pirate queen named Lai Choi San (Loi4 Coi4 Saan1 來財山), whose twelve-junk fleet may not have rivalled Cheng I Sao’s armada but nonetheless inspired a succession of “dragon lady” archetypes in twentieth-century fiction. “What a woman she was!” Lilius gushed in his book:
Rather slender and short, her hair jet black, with jade pins gleaming in the knot at the neck, her ear-rings and bracelets of the same precious apple-green stone. She was exquisitely dressed in a white satin robe fastened with green jade buttons, and green silk slippers… What a wealth of material for a novelist or journalist!
On that account, few could disagree. But since the publication of I Sailed With Chinese Pirates some have questioned whether the “the Queen of the Macao pirates” existed at all. Unlike the diaries of the captive Richard Glasspoole, the events and characters in Lilius’ account cannot be attested to by other sources – in fact, the only accounts of Lai Choi San are from Lilius himself, whose reliability has also been called into question. Variously described as American, English, Swedish, Finnish, Russian, or some amalgamation thereof, Lilius was eventually brought up on fraud charges in Singapore and the Philippines.

Mysterious pirate queen Lai Choi San inspired a succession of “dragon lady” archetypes in twentieth-century fiction
Unfortunately for the world of buccaneering lore, it’s possible that the most memorable pirate of twentieth-century Hong Kong was no more than a work of fiction.
By the time of Lilius and Lai Choi San, piracy on the south China shores was breathing its last. Isolated cases continue to break out in the uncertain years of the Second World War and the Civil War between the Nationalists and Communists that followed. Most notably, the 4,500-ton Dutch motorship Van Heutz became the largest ship ever to be pirated on the South China coast in December 1947. But it was clear to see that the writing was on the wall for the unworthy successors of Cheung Po Tsai and Cheng I Sao.
True to form, however, Hong Kong’s pirates wouldn’t go out with a whimper but with a bang. In 1948, a Cathay Pacific boat plane called Miss Macao became the first commercial aircraft ever to be hijacked. Four men attempted to take over the plane as it flew back from Macau. They hoped to hold its millionaire passengers hostage, but in the ensuing melee they shot the pilot and sent the plane hurtling into the sea, killing all but one of the 27 people onboard. The sole survivor was one of the so-called “air pirates,” who went unpunished thanks to a legal loophole: the only relevant laws pertained to piracy at sea, which could not have been committed in an aircraft.
The shadow of skyjacking that went on to cast a terrifying pall over the age of aviation and claim so many innocent lives owed its origins to this ignominious Hong Kong first – a fitting final shot from the ladrones who once called these islands their own.