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Respectable heads of state rarely admit to keeping company with gangsters. But in April 1927, about 15 years after the collapse of the last imperial dynasty, Chiang Kai-shek and China were at a crossroads. Chiang had followed a murky path to leadership of the Chinese Nationalist Party, the Kuomintang. Although the Kuomintang was rivaled by an assortment of warlords who ruled the provinces as their personal fiefdoms, in Chiang’s mind the greatest obstacle between him and control of that vast and war-torn country was a young Communist Party which, he believed, would soon be nothing but lethal trouble.

So generalissimo Chiang turned to Du Yuesheng of the infamous Green Gang of Shanghai, a criminal brotherhood rooted in equal parts menace and murk. Du was the leader of this criminal enterprise, and the bloated, gleaming international city lived and died by his word. It was the power of death which most interested Chiang that spring. He wanted nothing less than complete power over all of China, and to get it, he was willing to trade the lives of thousands and allow the establishment of a vast narcotics empire. Others might have balked at trading the murder of a few thousand political opponents for this goal, but neither Du nor Chiang felt any such hesitation.

Du Yuesheng’s life began in misery. Before it was all over, it would take him through unspeakable power, obscene wealth, international infamy, and final obscurity. At the time of his birth in August 1888, the Manchurian Qing dynasty, China’s last imperial government, was rapidly waning, and Du’s birthplace witnessed one of the Qing’s greatest humiliations.

As the Qing’s power failed throughout the 19th century, foreign colonizing powers embarked on a series of wars to seize as much Chinese territory as they could get their hands on. Among them were the United Kingdom, France, Italy, the United States, Germany, the Netherlands, and Japan, each of which had steadily carved out chunks of China’s coastal cities. Officially titled “concessions”⁠—in that the Qing had formally given them up, albeit at gunpoint⁠—a string of foreign settlements soon sprouted along the length of China’s coast. In these enclaves, expatriate Westerners built their own homes, schools, factories, and governments, insulating themselves from all things Chinese while extracting staggering profits from the steady stream of labor pouring in from the surrounding regions. Foreign residents of the concessions could not be tried by Chinese courts, paid no Chinese taxes, generally held no respect for the ailing empire, and spent their days surrounded by the comforts of Europe, America, and Japan. Meanwhile, beyond their walls, China’s vast population grew ever more destitute and desperate.

Shanghai, at the mouth of the Yangtze River, was the crown jewel of these colonial cut-outs, with France holding one concession and Britain and the U.S. jointly governing another. Home to thousands of “Shanghailanders,” as the city’s foreign-born residents called themselves, it was the envy of Asia, home to the region’s wealthiest companies, and the premier destination for anyone who wanted to have a good time east of India and north of Singapore. Besides wealth, the vacuum left by the deboned Chinese legal authorities meant the city offered a limitless supply of sex, drugs, gambling, and practically any other vice imaginable. With no unified immigration system, Shanghai was the only city in the world without any bothersome need for visas or official residence permits, and free from anything like vigorous law enforcement outside of the well-preened streets inhabited by the well-to-do. Shanghailanders from the treaty powers⁠—those countries with a seat on the powerful Shanghai Municipal Council⁠—were willing to tolerate all manner of decadence outside of the residential districts, so long as they were free to take part as they pleased and it didn’t upset the all-important banks and commercial concerns which steadily filled their pockets to bursting.

In contrast, Gaoqiao, a small town which has since been swallowed up by Shanghai as the metropolis sprawled steadily outward, wasn’t much to look at in the late 19th century. Positioned on the far bank of the Huangpu River, opposite the looming skyscrapers of the International Settlements and the commercial sector, Gaoqiao was home to just a few of the many thousands of Chinese porters, servants, merchants, and others who kept the city running. The district they lived in, Pudong, was the most desperate slum in the country, home to the millions of workers who streamed into the province of Jiangsu surrounding Shanghai, without whom the most wealthy, and corrupt city in China would have ground to a halt.

When Du was a boy, his parents were among them. His father ran a rice shop part-time and worked as a day laborer when he could manage to get onto a local work gang. His mother, a washerwoman, died when Du was three. Struggling to stay afloat, Du’s father made a tragically common choice for the time, selling his baby daughter into slavery. Du was sent to be raised by his uncle, serving as an apprentice carpenter. Du made two personal discoveries during these formative years: he hated manual labor, and he loved gambling. Already, by the age of four, the precocious gamesman was enamored of back-alley games of fan-tan, dice, and paijiu, a high-stakes game nicknamed “eating dog meat,” with the neighborhood boys. Before long, betting was his main interest, and he eagerly stole from his uncle to fund his habit. Four years later, his uncle, exasperated by the combination of laziness and sticky fingers, kicked the 8-year-old back to his father’s house.

There wasn’t much relief to be had there, either. His father had died when he was five, and Du was raised by his stepmother for the next few years, surviving by running the rice shop. Just four years later, that, too, came to an end when local Triad members kidnapped the young, pretty widow and reportedly sold her to one of the city’s many brothels, leaving the 9-year-old boy to fend for himself.

By the age of 14, Du was a veteran gambler, without a formal education or honest prospects, and completely alone. With little left for him in Gaoqiao, he moved downriver in 1902, into Shanghai proper to seek his fortune. From his humble hometown on the outskirts, the young man had come to the biggest, most glamorous, and most thoroughly rotten city in China, a place where people like him were forced to work to prop up the looming towers in exchange for scraps. It was, according to a popular saying of the time, “a thin layer of heaven on a thick slice of h#ll.”

Du spent the next few years eking out a living, whenever and wherever he could, until he finally secured a steady job as an apprentice with the Da You Fruit Company along the wharves in Shanghai’s Old City. The next five years would be spent at the fruit stall, with his wages disappearing into wagers in after-hours gambling sessions. When he wasn’t flinging rotten fruit at well-dressed passersby, he was swiping from the till to fund his games. His employers, upon discovering the missing money, were even happier to show him the door than his uncle had been. This put a permanent end to legitimate work for Du Yuesheng.

Luckily, his gambling hadn’t been a fruitless waste. In the course of hundreds of games, he’d met and befriended some of Shanghai’s most disreputable denizens, including a fellow gamester and pimp nicknamed “Lot Drawer.” Sensing potential in gangly young Du, Lot Drawer sponsored his initiation into the Green Gang, a potent criminal organization which was steadily gaining currency in Shanghai’s underworld. With its roots in secret societies of boatmen on the Grand Canal, which stretched the length of Eastern China, the Green Gang had already existed for some 60 years by the time Du enrolled in the 1910s, although its members claimed it descended from the Luoist religious cult centuries before.

This distinguished institution furnished Du with a petty career as a numbers runner, extortion artist, and small-time opium dealer. He seemed destined for a life as one of the countless dockland hoodlums who made the streets a danger after dark. He also developed a fondness for the very opium he peddled, a habit which deadened his eyes and gave his already unsettling visage a grim, reptilian appearance with a permanently droopy left eyelid. Deciding to make an asset of his chilling looks, he began to shave his head in order to make his large ears stand out all the more prominently. In the process, he earned himself a nickname which would become an immortal part of the mystique of old Shanghai: “Big-Eared Du.”

He got his big break, however, when he met Huang Jinrong, known as “Pockmarked Huang” for the multitude of smallpox scars webbing his face. Huang had built a lucrative criminal career with the Green Gang, rising to become its boss before his near-encyclopedic knowledge of Shanghai’s underbelly brought him to the attention of the police in the French Concession some 20 years earlier. Rather than arresting him, the French Concession Police wanted an ally, someone whose knowledge and connections would allow them to make praiseworthy arrests, justify their budget, and reassure the concession’s governor that all was well. Pockmarked Huang, greedy, cunning, and capable, was the perfect choice, and in 1892, he was hired as a plainclothes criminal detective even as he continued to run the Green Gang.

Du might have gone unnoticed if not for meeting Lin Guisheng, Huang’s wife, a former brothel madame and the undisputed queen of Shanghai’s lucrative night-soil market. Taking a shine to “Fruit Yuesheng,” as the teenage gangster was then known, she pushed her influential husband to provide the blossoming racketeer with more and more responsibility. But Du was too savvy and too ambitious to remain “Fruit Yuesheng” for long.

After proving his mettle managing a small opium den, Du was brought into the real moneymaker: managing one of Huang’s enormous dens in the French Concession itself, where the opium trade enjoyed the protection of French police, and the blind eyes bought with Huang’s influence and silver dollars. For more than 10 years, Du served as Huang’s trusted lieutenant, collecting his cut of the profits, enforcing order among the gang, and scaring local merchants into line. It was more than enough time for a few schemes of his own to take shape.

Despite sitting on a narcotic gold mine behind a sheer wall of power and protection, Huang was a man of limited vision. A gangster of the old school, he was content to issue French-sanctioned licenses to opium den owners and skim a percentage off for the Green Gang and himself. For him, life on top meant enjoying a steady, if sedate, stream of quiet profits and reveling in his own imagined untouchability.

Shanghai shattered his illusions when it reached out to touch him in 1924. Huang doted on a popular singer, showering her with gifts and even building her a personal theater. One night, he hurried along to the singer’s mansion to attend an opera performance. Also attending was a noted Shanghai playboy and, more importantly, the son of a powerful local warlord. During the performance, the drunken playboy, apparently deciding he didn’t care for the singing, loudly booed and heckled the singer. Huang, incensed and sure of his own power, had his bodyguards beat the young sop before booting him off the premises. Confident that the matter was settled, he went back to his seat and enjoyed the show.

A few nights later, at the same theater, Huang was taking in another performance when several men burst into the stands, made their way to his seat, pressed pistols to his head, and hauled him off to a cell for a vicious beating. The warlord’s son had refused to accept Huang’s insult, and drew on his father’s influence to exact his revenge. Neither the French nor any other foreigners had ever allowed any Chinese soldier to set foot in their concession, and the fact that they’d been allowed in to effect the humiliating arrest was a sure sign that Huang was losing favor.

Upon hearing of the Green Gang godfather’s arrest, Du Yuesheng saw an opportunity. For years, he’d grown quietly frustrated at the unambitious pace of Shanghai’s drug trade, and realized that a sharp-minded operator could transform the sale of opium, morphine, and heroin in China’s biggest drug market into a single, fabulously profitable enterprise. Huang had always been too old-fashioned to do it himself. Du was more progressive.

Gathering a fortune in bail money, Du and his fellow second-in-command Zhang Xiaolin extracted the shame-faced boss from jail. Huang had lost face in more ways than one. To begin with, his lack of real power had been publicly and personally demonstrated during his arrest and beating; for another, he’d had to rely on his underlings to regain his freedom. Huang could no longer delude himself that Du was a mere lieutenant, and was forced to accept the younger mobster as a (nominally) equal partner. In reality, Du had just pulled off the most genteel coup possible, toppling his superior without taking his life, a stark contrast to the willingness with which most Green Gang men murdered one another. The following year, one of Huang’s rivals paid the proper bribes to have Huang ejected from his lucrative position with the French Concession Police. The old man was relegated to the status of an honored elder, respected but powerless. Du Yuesheng was now the real power in Shanghai.

Huang, Zhang, and Du formed the Sanxin Gongsi, or Three Prosperities Company. Ostensibly governed jointly but in fact the private preserve of Du himself, its purpose was to manage the streamlined drug industry. Du’s personal subsidiary, the Black Stuff Company, named for the color of the sticky, tar-like drug which was its stock in trade, taxed the opium dens in the French Concession at a rate of 30 cents per night for each opium pipe in use. The smuggling, refining, sale, and use of opium, combined with legitimate businesses in their names, generated a gushing stream of as much as $60 million in the Three Prosperities Company’s first year alone⁠—about $913 million in U.S. dollars in 2021⁠—equivalent to as much as 20 percent of the state’s revenues. This money went to paying for a sprawling French Concession house for Du, greasing the palms of the politicians and warlords to whom Zhang acted as diplomat, and feathering Huang’s retirement nest.

The Shanghai Municipal Police (SMP), which served the larger international settlement governed by the U.S. and the U.K., had grown alarmed by the rising opium trade even under Huang’s more relaxed rule, but were nearly powerless to stop it. The Green Gang held the loyalty of the beggars who dotted the Concessions’ streets, who acted as a network of scouts and spies, alerting Du’s men to any potential trouble. What’s more, police from each of the three sections of Shanghai⁠—the French Concession, International Settlement, and native Chinese areas⁠—were barred from entering the other areas, and criminals and suspects in each could only be extradited after a long and byzantine application which offered ample time for a getaway. With the police divided and hamstrung, opium dealers were confident enough to place their names and addresses on packets of opium.

By the early 1920s, the SMP had begun cracking down on the sale and production of opium within their territory, but by that point, Du and his companions were so incontinently rich that they didn’t care. The opium traffic swelled so heavily and was carried on so brazenly that in 1930, the maverick journalist Bertram Lenox Simpson wrote:

“The Shanghai opium trust has its headquarters in the French concession, where its stocks are safely stored under police immunity. More than 20,000 chests of Persian, Turkish and Indian opium are stored there annually. In addition, 1,500 chests of Chinese opium are stored there monthly, bringing a total of 6 ½ million dollars to those controlling the opium traffic. I could name the street in the French concession where the head depot of this trust is situated. There are 200 foreigners working in and around Shanghai for the opium trust, and 40 miles outside the Shanghai harbour there is a port for trans-shipment of overseas shipment of opium.”

Simpson’s persistent threats to reveal the location of the depot came to a short, sharp stop soon after, when a young bespectacled Chinese man in a suit knocked on the journalist’s door one evening, handed him a calling card, and shot him dead with an automatic pistol. The murder was never solved.

Glad-handedness with assassins notwithstanding, Du endeared himself to Shanghai. Unlike the miserly Huang, Du had already begun burnishing his reputation as an open-handed philanthropist. He threw parties for well-known, if disgraced, politicians, provided relief to victims of warlords’ squabbles in nearby Zhejiang province, and spread money around town on any number of charitable causes. As Du put it, “I don’t save money; I save friendship.”

Behind the benevolent public persona, however, was a ruthless kingpin: by 1927, nothing criminal, illegal, or even questionable took place in Shanghai without Du’s say-so, and any crook who dared to knock over a safe, rob a well-heeled Westerner, or run a quiet numbers game without giving the Green Gang their cut was liable to end up shot, kidnapped for ransom, or with their tendons sliced apart with a fruit knife. When Du wanted a stop put to something, he’d send a coffin to the house of the one who needed stopping. Few failed to get the message.

Under this iron hand, Shanghai’s underworld quickly fell in line behind the new boss. Even the city’s foreign residents were subject to Big-Eared Du’s governance: in a singularly sinister episode in 1932, several French officials who’d displeased him died mysteriously after eating mushrooms at a banquet held in their honor. Not long after, a ship carrying a French journalist who’d boasted about publishing a scandalous story⁠—in all likelihood, the grisly details of the poisonous mushroom meal⁠—happened to catch fire and sink in the Indian Ocean. No story, no problem.

It was Du’s reputation for largesse, brutality, and efficiency which made Chiang Kai-shek sit up and pay attention in 1927. Chiang was a rising military leader in the chaos following the 1911 Revolution which toppled the Qing dynasty. He’d been a founding member of the Kuomintang, or Nationalist Party, a group dedicated to leading China into the wider world as a powerful Westernized state, and had succeeded founder Sun Yat-sen as its leader upon his death. Despite his later notoriety, records of those early years are patchy, at best. Chiang may even have joined the Green Gang himself, but with surviving records muddled, missing, or simply destroyed, it’s impossible to say for sure. What’s certain is that, when the young Chiang left Shanghai in 1919 to build his army in the south, it was Huang Jinrong who paid his travel expenses, and the budding generalissimo never forgot the favor.

In 1926, Chiang, increasingly exasperated at the influence of petty warlords, gained the command of the National Revolutionary Army, the armed wing of the Kuomintang. Leading this Western-style, Soviet-backed force north from Guangzhou, he battled his way along the coast, dispatching or absorbing the forces of the warlords until, by March 1927, he had reached the edge of Shanghai. After a show of token resistance from a White Russian-crewed armored train, the commander of the city’s defenses promptly surrendered his troops with barely a shot fired, and fled in disgrace.

Just a few months after setting off, Chiang was poised to seize control of the largest and most prosperous city in the country, the site of much of China’s foreign trade, most of its factories, its largest and richest banks, modern shipyards, decadent nightclubs and casinos, and fully half of all the cars and trucks in the country. It was also, unfortunately for Chiang, home to the largest and best-organized group of the country’s communists.

For four years, the Nationalists and the Communist Party of China had been in an uneasy alliance of mutual vitriol, with the Nationalists hoping to snuff out the appeal of communism while the communists hoped to co-opt the larger party to spread their message of land reform, anti-corruption, and limited democracy. As this ill-fated partnership festered and collapsed from within, Chiang decided that, like the warlords, he’d had just about enough of the communists.

Meanwhile, within the city, Communist leaders had seized their chance to enhance the prestige of their party just as the warlord armies vacated. They’d been established in Shanghai for some years, time not spent idly, and the teeming labor unions they’d built up among the more than 40,000 factory workers and other assorted laborers were a formidable force. Outside of the International Settlements, Shanghai was now Communist country, with workers’ soviets controlling every aspect of infrastructure, work, and daily life. Chiang’s prize metropolis was booby-trapped by his rivals’ efforts, and before he could tap the bottomless wealth of the city, he needed to dislodge them.

The trouble was that the Shanghai Municipal Council would never tolerate Chinese troops within the boundaries of the International Settlement. What’s more, thousands of Chinese students and workers loudly protested the presence of the Nationalist general, demanding his resignation and departure and threatening to undermine any victory that might still be had. Chiang needed an inside man. As Chiang prowled around the city’s rim, Huang Jinrong paid a visit.

Huang relayed a proposal from his underling-in-name, Du: Chiang, who had only a few thousand soldiers, some of whom had been skimmed off the top of the evaporating warlord forces and could hardly be trusted, would be given the support, wealth, and connections of the Green Gang, as well as the implicit backing of Shanghai’s extensive business class. In return, he was to remember who his friends were and look the other way as to where his money came from. Chiang readily accepted, and then the real power-broker showed his face.

Du went right to work pumping his well-paid contacts in the foreign community for help, obtaining hundreds of weapons from the French and the Americans with which to outfit his private militia. Given the choice between the terrifying prospect of a self-governing working class or mafia rule, for the Westerners, the choice practically made itself.

Du also tried to make his men’s upcoming job easier by inviting the head of the largest trade union to his home for dinner on the evening of 11 April 1927. The organizer dutifully appeared, but when told that it’d be in the best interest of his union and his physical health to switch sides and oppose the communists, he unwisely balked. The beating which ensued was only stopped when Du wafted to the top of the grand staircase in an opium-laced haze and cried out “Not here! Not in my house!” The chastened gangsters wrapped their victim in a burlap bag, drove him out of the French Concession, and, ignoring his moans, buried him alive.

In the early hours of 12 April, about 2,000 denim-clad militiamen in Du’s employ poured into the streets, mingling with union members and spreading to district offices, factories, and infrastructure sites throughout the city. At dawn, a prearranged signal consisting of a bugle call and a gunboat siren shrilled out, and the Green Gang men set to work murdering every communist and union member they could lay hands on. Men were beheaded in the street, groups of protesting workers were rounded up and shot en masse. Thousands more were tied together, shoved into trucks, and shipped off to prisoner camps to be held without trial. A gruesome rumor spread that captive railroad workers at Shanghai South Railway Station were dispatched by being burned alive inside of their own locomotives.

By nightfall, Green Gang militiamen had slaughtered as many as 5,000 workers and communists in the Shanghai massacre. The top brass of the Communist Party of China⁠—such as CPC chief Chen Duxiu and his deputy, Zhou Enlai⁠—slipped out of town as quickly as possible and regrouped with their allies as the Chinese Civil War began in earnest, and Shanghai’s merchant class rejoiced. For Chinese businessmen, that satisfaction didn’t last long though, since Chiang had little respect for capitalists other than as a source of money, and his Green Gang friends didn’t disappoint. The unions were finished, but merchants soon found themselves paying a far higher cost for their peace of mind. If businessmen failed to pay into the Nationalist war chest, Du Yuesheng’s bruisers were on hand to kidnap their sons in exchange for hundreds of thousands of dollars in ransoms. His pockets fat and his Communist rivals shattered, Chiang finally had his victory, his city, and a genuine partner in crime who would soon prove himself to be the Nationalist commander’s greatest ally and the most persistent thorn in his side.

Du likewise came out of the Shanghai massacre in an altogether better position than before it. He and his fellow gang leaders were each given the honorary rank of major general in the National Revolutionary Army. A lump sum paid to the International Settlement regained him the right to manufacture and market drugs within its borders. With the communists broken and the warlords sent packing, the French were under no illusions as to who was in control outside of their tree-shaded enclave. They amicably extended Du’s drugs license even further, guaranteeing his opium-laden riverboats the protection of the French Navy. The largest chunk of money Du sent upriver to Chiang, the first of many illicit paydays and the start of a beautiful friendship.

Chiang, however, now found himself in a difficult position. His marriage of convenience with Du Yuesheng had put Shanghai, and all the wealth it contained, in his back pocket. But the Shanghai Municipal Council haughtily demanded that he prove to them that he and his new government, based in the ancient capital of Nanjing, were capable of managing their own homeland. For that reason, and to at least be seen to contain the frightening growth of Green Gang power, he had to establish a new police force as well as make a public effort to stem and undo the spread of opium.

Opium had been officially prohibited in China for more than a century, first by the old Qing dynasty and then on a province-by-province basis throughout the shambling republic. Opium suppression bureaus, ostensibly formed to enforce this ban, were frequently little more than a source of quick cash for whichever warlord happened to be in charge in a given area. This is precisely what had happened to the Shanghai Opium Suppression Bureau, and Chiang quickly abolished this agency as a public show of commitment, demonstrating to the Westerners in Shanghai that his government was, unlike the warlords, serious about combating the drug trade.

In its place, Chiang established the Jiangsu Opium Suppression Bureau, with Du Yuesheng at its helm. To observers, this was suspiciously like placing a fox in charge of a chicken coop. But Du was a powerful ally, and one who could transform the sticky black opium into precious dollars. Chiang needed to extend his control over China through military means in the face of stubborn warlords and an increasingly aggressive Japanese Empire. For all his party’s professed ideals of incorruptibility and honesty, there were no depths to which he wouldn’t stoop.

In the Qing dynasty’s halcyon days, it would have been a simple matter to levy taxes to fill the government’s coffers. But Chiang didn’t have that advantage. He’d inherited a country torn into dozens of petty states, menaced by aggressive neighbors, riven with poverty and crime, and bullied by well-monied foreign settlers. On top of that, Communist forces in the central and southern provinces stubbornly refused to be defeated, inflamed by the brutality which Chiang had inflicted in Shanghai. He had to act fast to build his army and furnish his government with the funds needed to operate effectively, and to get it, he turned to the quick-fix lure of drugs.

Mere months after Du’s ascension to the national backstage, the International Opium Commission noted that “Millions have been raised out of opium for military operations and civil propaganda […] the Government is raising the very last cent out of the cultivation and use of opium.” T. V. Soong, China’s finance minister (and brother-in-law to Chiang Kai-shek, the financial tycoon H.H. Kung, and Kuomintang founder Sun Yat-sen) had argued for legalizing this fantastic cash cow and nationalizing it. However, Chiang was forced to acknowledge the reality that Du had already achieved this. Not only did it make little sense to antagonize his underworld ally by muscling in on his prize racket, it would make even less money. Instead, Nanjing and Shanghai settled into a sordid partnership with seemingly limitless potential for growth. The partnership soon bore fruit: when the Nationalists forcibly took over a series of large banks, it was Du who persuaded the banks’ directors that they were “fatigued” and should resign. The president of the Bank of China was told to keep his protests to himself if he knew what was good for him.

Du, meanwhile, carried on in grand splendor. Wearing rich, elaborately decorated robes adorned with three preserved monkey heads for luck, he put his $40 million fortune (worth about $815 million in 2021 dollars) to use in building a grand mansion on Avenue Edward VII (now Yan’an Road), just north of the old walled city and within sight of the banks and hotels along the Bund. Inside this traditional house were four wives, several concubines, eight sons, three daughters, and a squad of hulking White Russian bodyguards. When he went to nightclubs and cabarets, he surrounded himself with “three or four ‘sing song’ girls decked in mink and diamonds” and two carloads of heavily armed bodyguards at all times.

Du’s connections to a panoply of prominent figures, both legitimate and otherwise, greased the treads of his efforts to reinvent his public image as an upstanding pillar of the business community. By the time he earned his first mention in 1933’s Who’s Who in China, he had gained an innocuous reputation as a “banker and public welfare worker.” Nowhere in the list of occupations, chairmanships, and board positions that filled out the remainder of the entry was the word “opium” to be found. The fact that Du’s Zhonghui Bank was the perfect instrument for turning gambling and drug money into clean, respectable profit must have fallen under his innocent description as “the director of many other Chinese commercial […] organizations.” Ralf Sues, a Polish expatriate journalist who interviewed Du in the 1940s, offered a pithier assessment: “A combination of Al Capone and Rockefeller.”

Not all of his wealth went toward skulduggery, however. Du’s other new passion was showmanship. In June 1931, he put on the biggest show Shanghai had ever seen when he dedicated a temple to his ancestors. After the ceremony, a parade in his honor trudged through town for hours, with British police and French gendarmes riding ahead of banners emblazoned with his name, along with thousands of hangers-on and well-wishers in a line nearly two miles long.

The deafeningly loud procession finally came to a halt at the Source of Golden Profit Quay, where Du and his party were ferried across to his native Pudong, where the staff of one of the city’s most famous restaurants had been ordered to relocate to cater for the three-day party that followed. Thousands of meals were served every day while Beijing opera stars serenaded the crowds during what was, in effect, an announcement that Shanghai was under new management.

Du splashed out for civic causes, donating two dozen stone bridges to the city and paying to renovate a treasured temple, and he chaired several local charities and schools. When the Pudong Tongxianghui Building, a “grand eight-story edifice designed to shadow over every building in the neighborhood,” was erected on his street, the auditorium within was dubbed “Du Hall.” During the opening ceremony, attended by the Kuomintang and business elite, two men stood on stage inside: the mayor of Shanghai and Du Yuesheng.

Du had emerged as the darling of a city enamored of his grandiosity and sheer power. Even his gruff, working class Pudong dialect became fashionable. Decades later, an old Green Gang hand claimed that, during the zenith of Du’s power, “loafers and their friends could all say a few sentences of Pudong dialect in order to show off, implying that they had connections to Du’s group and that they were not alone in the world.”

All the while, Du’s drug factories cranked out more than $5 million in tax revenue for Nanjing every year (about $92 million in 2021 dollars). Largely retiring from active management of the Green Gang, Du’s years of overindulgence in his own medicine began to show. Decades of opium use had transformed the once-daunting kingpin into a shambling shadow of his former self, “shuffling along, listlessly turning his head right and left to look whether anyone was following him” with ”eyes so dark that they seemed to have no pupils, blurred and dull⁠—dead impenetrable eyes.”

After 30 years of intimidation, intrigue, calculated violence, and shrewd ambition, Big-Eared Du finally had everything for which he’d worked and schemed his way up from Pudong. For a man who’d spent his entire life looking up, there was nothing more to look up at. That didn’t mean that he would drop Shanghai’s reins from his opium-stained fingers anytime soon, though⁠—not even when the greatest threat China ever faced came to pry them loose.

In 1937, the Empire of Japan formally declared war on the Republic of China, officially converting a six-year-old cold war into a hot one. In July of that year, Japanese troops marching south from Manchuria came to a halt outside of Shanghai, determined to seize the city. Japanese war planners were motivated by the same greed which, 10 years earlier, had driven Chiang to capture Shanghai, with the bonus that doing so would humiliate the Chinese premier and, to an only slightly lesser extent, the foreign powers huddling within the concessions.

In a gesture of support, Du donated his bulletproof limousine to the Chinese army, although the extent to which it might have helped the soldiers avert the crushing defeat which followed is unknown. Over the course of three months, the Imperial Japanese Army smashed the defending National Revolutionary Army to pieces, cutting whole divisions down by half. Finally, as Japanese forces poured into the city in early November, Du knew that it was only a matter of time before stiff-necked officers would come calling to either persuade him to join them, or to snatch away his properties. Du quietly took inventory, calculating which opium dens, gambling venues, and brothels were likely to be seized by the occupiers, assigning trusted lieutenants to the remainder to keep his cash flowing. Then, with one of his wives in tow, he left town. As unfortunate as the invasion was, he failed to see why he should share the sorrows of the city he’d lorded over for decades.

The cash which had passed between him and Nanjing, he figured, had to count for something. Soon after establishing himself in Hong Kong, he paid a visit to Chiang in his wartime capital at Chongqing. Since it was his money which had paid for many of the rifles now clutched by battered Chinese soldiers, he was quickly granted an audience with the hard-pressed leader. Du wanted to reaffirm their old friendship and, like old friends do, wanted Chiang to focus on retaking Shanghai. However comfortable Hong Kong was, the Green Gang chieftain clearly preferred his old haunts. But Chiang was pragmatic about his minimal strength to oppose Japan, and his response to his longtime ally was, in summary, a firm “nothing doing.”

Du sat on the board of directors of the Bank of China, held a high position in the Chinese Red Cross, and even deputized thousands of Green Gang members to act as a guerrilla unit within Shanghai. But for all the grand titles and respectability he’d garnered, his usefulness was coming to an end.

After a long and brutal Second World War, an exhausted Japan finally surrendered to the Allied powers, China among them, in August 1945. In the eight years preceding their defeat, Japan’s most effective opponents had been the same communists suppressed by Chiang and Du 20 years before. With the invaders gone, a surfeit of their weapons left behind, and millions of starving, landless peasants fed up with the Kuomintang’s excesses, China entered a new period of civil war. Ending his long exile now that the coast was clear, Du returned to Shanghai expecting a red carpet. Instead, he found a city ground under the heel of invasion, embittered, and with little patience or respect for one who’d abandoned the city in its darkest hour.

Chiang realized belatedly, once again, that he had to take a stand against corruption in an eleventh-hour bid to regain the sympathy of the population. The communists, under the leadership of Mao Zedong, were immensely popular among China’s poorest, with the promise of land reform proving irresistible. It was no longer easy to overlook the misery-inducing source of Du’s wealth. Perhaps more importantly, the Nationalists, with an economy ruined by war, were now more desperate for money than ever before. Just as Du had strong-armed Shanghai’s merchants into filling Chiang’s coffers in 1927, he was now a target for the same treatment.

The downfall came in 1948, when Du’s son Weiping⁠—a stockbroker on the Shanghai Stock Exchange⁠—was arrested on Chiang’s orders, accused of stock manipulation, and publicly paraded in handcuffs. Huang Jinrong had been humiliated when forced to rely on Du to bail him out of jail decades earlier. Du⁠—more untouchable than his old boss had been, more wealthy, better loved⁠—was forced to bear the shame of seeing his own son branded a criminal in newspapers across the country.

Now 60 years old and aged before his time, the wizened Green Gang boss secluded himself in his Hong Kong mansion in disgrace. Chiang, his army wilting beneath the communist advance, retreated to Taiwan in December 1949, and Du wisely decamped once more to Hong Kong, never to return to the city he’d once held in the palm of his hand. The tired old gangster lived in modest obscurity with his fifth wife, a Beijing opera star, as his old ally set up shop in Taiwan.

As Shanghai swelled into a vast metropolis over the years, all that was left to mark the deaths of 5,000 workers and students was an austere monument in Longhua District, where many had been killed in captivity. Although political violence and corruption were nothing new in China, Chiang and Du’s unique and extreme relationship set in motion both the downfall of the Nationalist regime and the rise of the markedly more brutal Mao Zedong.

Remnants of the Green Gang escaped to Hong Kong and Taiwan, where they attempted to reestablish their heroin operations. But as outsiders burdened with a ruined reputation, they were soon swallowed up by local gangs. Nevertheless, the Green Gang’s technical expertise was widely admired, and their drug labs may have been maintained by their victorious rivals even up to the early 1990s.

Du preceded the Green Gang in death on 16 August 1951, still wistfully contemplating a return to the city which was once his treasured possession. For decades afterwards, Communist leaders still stung by the violence with which he had treated their comrades forbade any mention of his name, damning his memory and making it a criminal offense to publish articles or books about him. After reforms were introduced in the 1970s, this restriction was gradually relaxed, and soon the mythologized story of “the emperor of Shanghai” became a popular topic for pulp writers and a recognizable character in movies and television.

Although the alliance between Du Yuesheng and the Republic of China had dissolved in acrimony long before, Chiang Kai-shek never truly forgot who his friends were. Two years after the old gangster died, Du’s remains were brought to Taiwan and interred in a private cemetery just outside of the capital. An inscription above his tomb grandly proclaims the honor, filial piety, and loyalty of the man buried within.

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