Broken Tooth Koi: Profile of a Triad boss

On the 1st of December 2012, one of the most infamous and feared Triad leaders of the past few decades emerged from a Macau prison after completing a 14-year sentence for loan-sharking, money-laundering and heading a criminal group. 59-year old Wan Kuok-koi, better known by his nickname Broken Tooth Koi, was once the imposing Dragon Head (boss or leader) of the dreaded 14K Triad society in the former Portuguese colony of Macau. This ill-reputed gangster was at the height of his power in the late 1990s, an era that saw wanton acts of criminality and bloody gang wars break out in the streets of Macau in a struggle for power and control. Broken Tooth Koi was known for his flamboyance, callousness, temperamental nature and his media hungry high-profile which gained him a reputation as a John Gotti type crime boss of the Far-East. Since his imprisonment the world he once knew has utterly changed after the Portuguese handed control of the former colony to the Chinese government in 1999. In this blog I take a closer look at the criminal career of Broken Tooth Koi and the obscure world of the Triad criminal societies.

One of Asia’s most notorious crime bosses, Broken Tooth Koi

The Triad’s originally sprang up in China centuries ago as patriotic secret societies dedicated to the overthrow of the Q’ing dynasty, which had been imposed by the non-Chinese Manchu’s from the north who had conquered China in the 17th century. The Triad’s original aim was to bring down the foreign emperors and restore the native Ming dynasty to the imperial throne. Ostensibly devoted to mutual aid and fraternity amongst fellow members, who were usually from a similar cultural or religious background, it wasn’t long before they began to engage in acts of criminality. The Triads were soon imposing protection rackets, enforcing the payment of tribute by junior members to the Dragon Head leaders and they became involved in the burgeoning opium trade which many Chinese people were hooked on.  The opium was brought into China by British “trade companies” who trafficked it to the Triad societies who in turn distributed it to the population at large.

After the fall of the Q’ing dynasty and the emergence of the Chinese Republic in the early 20th century, the Triads went from strength to strength. Triad Dragon Heads like Big-Eared Du, the mafia boss of Shanghai, wielded immense power within the new government. Corruption, vice and sleaze were the order of the day. The modern criminal societies that emerged in China had a rich cultural sense of themselves claiming to be the successors of the famous Shaolin monks. The Triads also have an elaborate initiation ritual which is similar in some respects to the Italian Mafia’s induction ceremonies. Today the Triads are a truly global crime phenomenon with branches in dozens of countries around the world boasting hundreds of thousands of members. They are involved in a whole host of criminal activities such as extortion, gambling, loan-sharking, drug-trafficking, prostitution, human-trafficking, fraud, arms-dealing and a vast array of legal enterprises such as nightclubs, restaurants, casino’s, stock market firms and the movie business.

The 14K Triad society, of which the subject of this blog Broken Tooth Koi is a member, was founded at the end of the Second World War. It was created by a Kuomintang anti-communist general called Kot Siu-Wong who sought to unite all the Triad societies of Southern China under one vast umbrella group to oppose the rising power of Mao-Tse Tung’s Marxist guerrillas. After the Maoist takeover of China in 1949 many Triads fled the firing squads of the communists setting up shop in the colonies of Hong Kong and Macau, and also in other Chinese communities across the globe.

Kot Siu-Wong, the anti-Maoist general who founded the 14K
Kot Siu-Wong, the anti-Maoist general who founded the 14K Triad society

The 14K were soon making their presence felt in the two colonial enclaves, rapidly expanding their criminal operations and clashing violently with established Triad societies causing a succession of ultra-violent gang wars for control. They gained a reputation for engaging in acts of vicious and shocking violence against anyone who got in their way. In one particularly notorious episode in the 1950s, the 14K organised a bloody riot that ended in the deaths of dozens of people, mainly innocent civilians and foreigners. A police crackdown wasn’t long in ensuing soon afterwards but this didn’t dent the ambitious aspirations of this brutal gang and the 14K soon boasted tens of thousands of members.

Macau is a tiny peninsula occupying only 16 square kilometres with a population of nearly 700,000 people, making it one of the most densely populated places on earth. It was colonised by Portuguese adventurers and traders in the 16th century with the approval of the Imperial Chinese authorities. The colonists built up Macau as a hub for Western trade in the Far East and it was at one point a jewel in the crown of the Portuguese empire.

The former colony of Macau
The former colony of Macau

By the second half of the 20th century, Macau was viewed as an economic backwater overshadowed by her more illustrious near neighbour Hong Kong, which at the time was ruled by the British. By the 1970s the weary Portuguese were tired of governing the colony and repeatedly tried to hand back power to the Chinese government. Macau has always been a mecca for gamblers from around the world with the industry being the territory’s most important economic activity. The Triads have long exerted a dominant influence on its casino’s and gambling houses and also with the side-activities associated with the gambling industry such as loansharking and prostitution. The Portuguese authorities adopted a hands-off approach to the organised crime groups and to a large extent tolerated the Triads.

Triad membership in Macau exceeds over ten thousand gangsters that are broken down into competing societies. The 14K exert the strongest influence in the city with around 5,000 members dominating most of the illegal activity. Their fierce rivals the Wo On Lok are estimated to have 3,000 members and what they lack in money and influence they make up for in ferocity. There are also several other smaller Triad societies operating in Macau that are vastly overshadowed by their two bulkier rivals however some of these groups are also renowned for their savage violence.

Wan Kuok-koi, aka Broken Tooth Koi, was born in 1955 in one of Macau’s poorest slums. His childhood was a particularly harsh one and he left school at a very young age after only a couple of years of formal education. He lived in the tough streets surrounded by, and more than likely in awe of, the older Triad gangsters who dominated the small colony. After leaving school the Wan Kuok-koi worked in menial jobs in restaurants and as a ticket tout but he was also associating with other youngsters similar to himself who didn’t want to spend the rest of their lives in abject poverty like their parents had.

A Macau slum, Broken Tooth Koi grew up in one just like this living in abject poverty.
A Macau slum, Broken Tooth Koi grew up in one just like this living in abject poverty.

The teenage Koi took his first steps onto the criminal ladder when he and six friends formed a street gang called the “Seven Little Kids”. Engaging in small-time shakedowns and petty crimes the seven friends made a name for themselves battling it out over turf with other Triad-affiliated street gangs. Broken Tooth Koi earned himself a reputation on the streets as a violent and capable enforcer, he was soon acting as a bruiser for more senior gangsters who began to watch the young wannabe’s progress.

The ambitious hoodlum endeavoured to cut a dash amongst his peers but earned his nickname “Broken Tooth” from breaking his front tooth after crashing a stolen car. By the late 1970s he had proved his guile, competence and ruthlessness to higher-ups in the 14K Triad. He was initiated into Macau’s most powerful criminal organisation as a 49, which is similar to the rank of soldier in an Italian Mafia family. This opened up a new level of criminality to the up and coming gangster, it is believed he was primarily engaged in the society’s gambling interests. He was also involved in violent confrontations with other Triad gangs as encroachment on each other’s turf is an all too common feature of life in Macau’s underworld. Broken Tooth Koi earned himself a deserved reputation for extreme violence who struck fear into his enemies. He was targeted for assassination by rivals several times, in each instance being shot or “chopped”, attacked with Chinese butcher’s machetes. In one of these machete attacks he lost the use of several fingers.

Broken Tooth Koi was known for his flamboyance and short temper.
Broken Tooth Koi was known for his flamboyance and short temper.

As a fully-initiated 49, Broken Tooth Koi also looked to enhance his status within the Triad by successfully expanding his business into loan-sharking. His earnings from the loan-sharking racket was soon making a lot of money for his bosses in the 14K Triad. Several prison stints in the 1970s and 80s was no impediment to Broken Tooth Koi’s criminal progress. He became known to his Triad superiors as a sharp, intelligent and ambitious gangster with a handy penchant for extreme violence. His burgeoning reputation within the Triad led to another promotion this time to the important rank of Red Pole. The Red Pole’s within a Triad society are key officers and enforcers responsible for its offensive and defensive operations. This rank is similar to that of caporegime in the Mafia and a Red Pole will usually have dozens of men under his direct control. He would also have had a large territory under his command and was responsible for protecting and defending it from rival triads. Part of his duties as a Red Pole was that he was expected by his superiors to expand his criminal operations into the territory of enemy Triad societies.

Broken Tooth Koi as a Red Pole was now entitled to a larger share of the 14K criminal proceeds which they made from a vast array of illegal, semi-legal and legal enterprises. All Red Pole’s in the 14K were ordered by superiors to open legitimate front businesses, so they could claim a legal source of income in the eyes of the law and to use as a criminal headquarters. Broken Tooth operated several hotels, bars and restaurants from which he could pose as a legitimate businessman and oversee his fledgling criminal empire.

His power within the 14K Triad in Macau was further boosted by the arrival of a Triad heavyweight called Ng Wai, aka “Street Market Wai”. Ng Wai was a Filipino-Chinese high ranking member of the 14K with extensive gambling interests throughout the Far East. He had decided to relocate to the Portuguese colony and he soon spotted the talents of the ambitious Broken Tooth Koi. The ambitious pair were quickly plotting a takeover of the 14K in Macau.

The old Dragon Head, Mo Ding-ping, stood in the way of the ambitious pair and their desire to control the enclave’s lucrative casinos. The aging leader must have caught wind of the plot but instead of staying to fight he fled for his life. Broken Tooth Koi now took over the enforcement arm of the 14K. He was soon making his presence felt imposing his rule with an iron fist and muscling in on the lucrative VIP rooms in the casinos. However his arrogant and brash style made him many enemies in rival Triads and within his own society. Broken Tooth Koi’s favourite haunt was the Casino Lisboa. This tacky casino and hotel was the centrepiece of Macau’s gambling industry and was owned by billionaire big-shot Stanley Ho, the colonies most powerful man who had dominated gambling for decades. Koi controlled the lucrative VIP rooms that were exclusively for high-rollers and he also ran his loan-sharking operations from here.

The Casino Lisbao, Koi's favourite hangout where he controlled several lucrative VIP rooms.
The Casino Lisbao, Koi’s favourite hangout where he controlled several lucrative VIP rooms.

In comparison to the more traditional Triad leaders of the past who tended to be low-key, Broken Tooth Koi was a flashy and high-profile mobster keen to make an impression. He cruised around town with his entourage in powerful cars and dressed in expensive suits generally causing a stir wherever he went. He also gave big-headed interviews to the media boasting about his exploits telling one American magazine “anyone who’s done something bad to me will never escape. I won’t kill him. I’ll make him take a voyage to another world”. He even had a movie made about himself and his rise to power. The film was called Casino and was made by a respected Hong Kong movie producer and starred internationally acclaimed actor Simon Yam who played the part of a Triad boss based on Broken Tooth Koi.

By the mid 1990’s Broken Tooth Koi’s power within the 14K continued to rise with young, violent men in the society gravitating to the brash, arrogant gangster. Although Ng Wai was the official Dragon Head of the 14K in Macau his relationship with Koi began to break down. Broken Tooth was soon disregarding his boss’s orders and he began flaunting himself as the real power within the Triad society. Ng Wai opened a new casino on Taipai Island at the end of 1996 but on the night of its opening Broken Tooth Koi’s men shot it up sending a message to his old partner that his time at the top was over. Broken Tooth wasn’t just making enemies within his own Triad, their long-standing rivals the Wo On Lok Triad, or Shoi Fong “Water street gang”, became aggrieved at the Triad leaders high-handedness and encroachment’s on their turf.

Simon Yam, an acclaimed actor who played the part of "Giant" in Broken Tooth Koi's movie "Casino", based on his life.
Simon Yam, an acclaimed actor who played the part of “Giant” in Broken Tooth Koi’s movie “Casino”, based on his life.

The Dragon Head of the Wo On Lok in Macau, known as Shui Fong Lai, was fed up with Broken Tooth Koi’s haughty rule at the helm of the 14K Triad and now challenged him in a mafia-style street war. Shoi Fong Lai was also looking to jostle his society into a powerful position before the Portuguese handed power to China in 1999. Things began to heat up in the colony with the Portuguese authorities looking the other way. Triad chopping’s and shootouts began to take place on a daily basis between the 14K and the Wo On Lok. The gang war caused the local economy to enter a downward spiral as tourists were too scared to travel to the gambling mecca. Western governments advised their citizens to avoid Macau at all costs due to the unremitting Triad violence on the streets.

On the 26th of November 1996, the head of the Macau governments Gambling Inspectorate, a Portuguese lieutenant-colonel was shot multiple times in a brazen rush-hour hit. He survived the attempt but it sent shockwaves through the colony as people realised the Triads had become so bold that they were now mounting day light attacks against government officials. Broken Tooth Koi was suspected of ordering the hit and the audacity of it would suggest that he was somehow involved. With the Chinese government take over just around the corner the Triad’s were looking to be ones in control when the People’s Army rolled over the border to take control of the colony.

The following year on a spring evening, 4th of May 1997, the Wo On Lok sent a message to Broken Tooth Koi. His right hand man and close friend Shek Wing-chueng was travelling in a car with two bodyguards near the Casino Lisboa when two motorcycles pulled up blasting the three men with automatic pistols killing them all. Broken Tooth was enraged at this direct insult to his power and was determined to get even with his Triad rivals.  He struck back at Triad leader Shoi Fong Lai by having his men shoot up his house and the front façade of his casino. Lai fled to Vancouver in Canada to avoid the wrath of the 14K but the gang war on the streets of Macau continued to rumble on. Shoi Fong Lai’s decision would prove to be a wise one. He is still a powerful Triad leader today worth billions of dollars.

By now Broken Tooth Koi had become the self-appointed Dragon Head of the 14K, with his old friend and now enemy Ng Wai in hiding from assassins. But with Broken Tooth now at the height of his power his arrogance and megalomania began to get the better of him. With the internal war within the 14K still ongoing and the conflict with Wo On Lok unresolved the new 14K Dragon Head now made the fatal mistake of ordering the murders of high-profile citizens. A Hong-Kong businessman, a police investigator and a nurse close to a rival Triad member were all killed by Koi’s gunmen.

A fire-bombed car the height of Macau's gang war.
A fire-bombed car the height of Macau’s gang war.

Up until now the Portuguese government had ignored or pretended not to notice the wanton violence taking place in the colony. But Broken Tooth Koi’s unassailable power and blatant attacks on civilians and government officials had now forced them into action. Passing tougher new laws they called in a tough crime-fighting cop to target the brash Triad leader and bring to an end his violent reign. Antonio Marques Baptista was determined to stop the unremitting violence that had so damaged the colonies reputation. He went after some of Broken Tooth’s close allies and locked them up in the summer of 1998 on extortion charges.

Broken Tooth Koi by now had let all the power go to his head and he believed himself to be immune to all danger. His own egomania could not allow any challenge to his authority and he now set out to kill or maim Macau’s new crime fighting cop. Baptista’s car was rigged with explosives but luckily for the cop his dog smelled the explosive’s before he was about to enter the vehicle. This time the Triad leader had gone too far and the Macau authorities were determined to make an example of him. Also in previous months there had been around a half-dozen Triad style slayings directly linked to Koi. Officer Baptista personally led the arrest of Broken Tooth Koi in a VIP room of the Casino Lisbao where he was sitting with his cronies watching his own movie Casino that was just about to be released.

The arrest of Broken Tooth Koi, the crime fighting cop Antonio Marques Baptista who brought him down is pictured on the left.
The arrest of Broken Tooth Koi, the crime fighting cop Antonio Marques Baptista who brought him down is pictured on the right.

The trial took place in the fall of 1999, just as the Portuguese authorities were to handover full control to the Chinese government. They were in effect cleaning up the colony before they left and the trial of Broken Tooth was part of this process. Security was heavy during the trial due to the deserved reputation for violence that Koi and his followers had gained. The 45 year old crime boss denied all the charges of course, stating that he was an “entertainment businessman” but the jury wasn’t buying it. The trial almost seemed to be a foregone conclusion after it emerged that the Macau authorities had built a small high-security prison specifically for Broken Tooth Koi and the inner core of his gang. He was found guilty of all the charges and sentenced to 15 years in prison, 22 of his followers were also convicted. The flamboyant gangster was unsurprisingly outraged at his sentence, denouncing the judge as corrupt and screaming obscenities at the press, police and anyone else who happened to be in the court as he was led out to start his sentence.

Broken Tooth Koi on his way to serve his 15 year sentence.
Broken Tooth Koi on his way to serve his 15 year sentence.

After the Chinese takeover of Macau, Koi’s lawyers attempted to appeal his sentence but it was rejected. He would have to serve out his full sentence in Coloane Prison. Initially he was the same old Broken Tooth Koi, issuing orders and threats from behind bars. But as the years passed the once media-hungry gangster was little heard from and just focused on finishing his sentence. He was eventually released from prison in December 2012 and told the world media that he wanted to be left alone to live a quiet life. Quite a change from the snarling, flamboyant and media hungry crime boss who had went to jail 13 years previously. But Broken Tooth Koi was certainly not stupid and he knew that the rules of the game had changed completely since the Chinese moved in.

Macau underwent a huge transformation while Koi’s was wallowing in jail. The Chinese opened up its gambling industry to foreign private investment and the Las Vegas conglomerates had moved in turning Macau into the world’s foremost gambling mecca. The old tacky casino’s had been transformed and the old colony would have been practically unrecognisable to Broken Tooth Koi. The Triads were still heavily involved in the casinos and the Chinese tolerated them but they were by no means dominant in the industry anymore. Also the Triad gangs operate on the understanding that they must keep violence to an absolute minimum, if they don’t the Chinese will crack down very hard on them. The only recent break with this rule was the “chopping” of Koi’s old enemy Ng Wai in his own casino in 2012, but Broken Tooth Koi was not thought to be involved in the attack.

The 57 year old crime boss released from prison in 2012.
The 57 year old crime boss released from prison in 2012.

Broken Tooth Koi has emerged into this new Macau an apparently changed man. A reconciliation has even taken place between him and his former enemies, such as his old boss Mo Ding-ping. Friends and foes within the Triad are believed to have given Koi a piece of their casino’s but only on the understanding that there can be no return to the bad old days of the late 1990s, there is just far too much money to be made in Chinese-run Macau for them to be squabbling and jeopardising everything in costly gang wars. It is uncertain what role he is playing within the 14K Triad today but it is doubtful that he is still the Dragon Head of the society. He is probably the world’s best known Triad but with Broken Tooth’s new understated profile we probably won’t hear much from the once boastful gangster any more. The brash boy from the Macau slum has far too much to lose.


15 thoughts on “Broken Tooth Koi: Profile of a Triad boss

  1. To: Mr. Wan Kuok-koi (Dragon Head 14K Triad)

    A Greeting ..

    I wanted to join as a member of the 14K Triad for INDONESIA region. I have the soul of a leader, loyal, honest and ready to accept and carry out any work ordered by the head of the dragon 14K.
    So I have to, while waiting for the opportunity and the confidence of the head of the dragon 14K, then I say thank you.

    Best Regards

    Liked by 1 person

      1. I think you are a great writer and I would love to buy your books. Just a suggestion, perhaps you can tell readers a little bit about yourself such as a name or even a photo. Keep up the good work.. I will definitely be sharing your blog with others 😃


  2. Why don’t you post a blog in regards to Donald Trump and his relationship with Danny Leung. Danny Leung was both a vice president for marketing at Trump’s Taj Mahal casino and an associate of the 14K Triad. “He was formerly a business partner with Eddie Louie, a 14K Triad member and the brother of Nickie Louie, aka Louie Yin Poy, a former leader of the Ghost Shadows Gang,”


  3. Nice blog and interesting info, iv enjoyed reading it.
    Looking forward to the RP piece, one of the first mafia books i read was by an associate of his i cant remember his name, Vincent something…. anyhow, cheers!

    Liked by 1 person

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