Massacre on Singapore’s Prison Island: A Prison-Without-Bars Experiment Gone Wrong

It was called The Island of Ease, though on one particular day, it was anything but.

On 12 July 1963, the prison on Pulau Senang, an island thirteen kilometres off the southern coast of mainland Singapore, burned. The flames that seized the land were not borne by accident. It was fuelled by implacable anger, and the rioters were drunk with the savagery of it all.

Superintendent Daniel Stanley Dutton was cornered into his office after getting attacked by three prisoners. He could hear the commotion outside, and the four walls suddenly felt like they were closing in on him.

A rhythmic, grating sound came from above his head. Two men had climbed to the roof and had hacked a hole in it with a small axe. Petrol spewed from the hole, soaking Dutton to his boots. The men tossed in fire, and the fire devoured Dutton.

With his clothing ablaze, Dutton rushed outside. Four others, all armed with axes and cangkuls, were waiting for him. They attacked him in an almost barbaric fugue, and when they were done, they burned his body.

A rioter’s shirt, stained red with Dutton’s blood, was hung up on a mast. It was a double-barrelled symbol of victory and surrender. There was no scrambling to flee the crime scene; it was in fact quite the opposite. As smoke polluted the air with an inky permanence, the rioters played music on a guitar and sang and danced. The incongruity of the scene was nauseating: jaunty carolling amidst a burning, mutilated body.

This is the story of the Pulau Senang experiment.

Law & Disorder

On the morning of 4 June 1959, Devan Nair, a founding member of the Peoples’ Action Party, strode out of Changi Prison with a resolve: he wanted to revamp the prison system.

The man had been thrown in jail by the British for his anti-colonial activities, and was released after Lee Kuan Yew and the PAP won the 1959 election.

Though he claimed to be treated well in prison, the same couldn’t be said for his fellow prisoners. He had found the conditions they had to live with egregiously demeaning. “For example, on the approach of a British prison officer, every convict had to kneel on the floor, with his head down,” recalled Nair. “That aroused my ire, and it still does when I think of it”.

Chinese secret society members in early 20th-century Singapore. (Source)

Overcrowding was also a major problem. The Singapore of the early twentieth century was one that was facing the secret society menace. These groups came with the arrival of Chinese immigrants who came into Singapore in the years following 1819. As more immigrants, or ‘Sinkehs’ continued to arrive, the size and number of these societies grew.

Along with the flourishing of secret societies came their rivalries, which made Singapore a dangerous place to live. For many years, murdered bodies were strewn throughout the country, with “each mutilated in a peculiar manner… with either the right or left hand chopped up into a certain number of parts, left hanging together by the skin”.

By 1939, they were no longer “politically subversive organizations” but “openly, dangerous criminal gangs existing for criminal purposes”. In that year, it was reported that there still existed 50 Cantonese, over 100 Hokkien and 20 Teo Chew gangs with an accumulated total of almost 16,000 members. Fights broke out for the most trivial of reasons – one resulted in a murder of a man the previous year because of a 20-cent gambling debt. Daggers and guns were wielded during these brawls.

The Criminal Law (Temporary Provisions) Act was passed in 1955 in response to this violence, and gave the police the power to “arrest anybody suspected of having acted or being likely to act in a way that could threaten security without evidence or warrant… and detain them indefinitely without the detainee ever being charged with a crime in a court of law”.

These wide-ranging discretionary powers together with increased police enforcement led to unintended consequences. Prisons in Singapore were becoming so overcrowded that some were set free before the end of their sentences. “Where overcrowding exists, cleanliness is impossible… Confinement to cells for 14.5 hours at a stretch… is a denial of reasonable access to the latrines and substitute arrangements constitute a possible menace to health,” reported the Malaya Tribune.

The Commission

Nair handing the commission’s report to Yang Di-Pertuan Negara Yusof Ishak. (Source)

In November 1959, a “Prison Inquiry Commission” was created to look into the issues that faced the system. Despite news stories that painted a rather holistic life in prison, one that had weekly film screenings and typewriting classes, the commissioners, led by Nair, discovered a different reality.

Reports from the commissioners indicated that detainees lived “18 hours a day in their crowded cells in unhygienic conditions due to the lack of adequate water supplies” and that the other six hours of day were spent in the yards. There, they described the men they saw as “squatting or aimlessly wandering around”. The detainees were also let out in two batches, according to their gangs (the 24 gang and the 08 gang). The practice was frowned upon by the committee as they had reckoned that it would only serve to strengthen the former gang affiliates and loyalties. 

Most striking was the observation that the men seemed to be void of any hope and dignity. Each day was a vapid passing of time, and its blandness only stirred resentment in the men at their detention. Their sole reading matter was said to be the “dubious type of illustrated comic literature” that offered only perfunctory stimulus.

And so, the government accepted the suggestion by the committee of an open prison on an island that sat 15 miles off Singapore called Pulau Senang, where gangsters worked their way back to society through toiling. It was on the basis that “the true object of the prison system is to achieve the rehabilitation of offenders so that they can return to the community as law-abiding socially useful persons”.

The commissioners were well aware that the scheme was a gamble, but it was a risk that they were willing to take.

“We would certainly regard the Pulau Senang Scheme as being in some degree experimental, but we do not consider that this is in any way to be criticised, when so little is known concerning the causes of anti-social behaviour and probably little more regarding their effective treatment,” they said.

The Plan

The rehabilitative scheme was to be carried out in four stages.

First stage. Detainees would enter Changi Prison “to be detained under the most rigorous conditions”. Though the detainees could choose if they would like to participate in the scheme, they were “encouraged” to volunteer. Perhaps it wasn’t so much of a choice than it was a subterfuge, given that any disinclination would be counteracted with a reduction in “amenities enjoyed at Changi Prison” and a risk of prolonging their sentences.

The island in 1960. (Source)

Second stage. Detainees who stayed for at least 12 months were permitted to move onto the island. The goal was to have the detainees learn that they were “members of a wider community with correspondingly wider responsibilities and wider loyalty then they now possess”.

Third Stage. Every month, the Prison Superintendent would submit 30 names for consideration to the Review Board, who would vet if their “conduct and industry” warranted a release. The police had the final say on who was released. On average, one had to be there for between 12-18 months before his name was submitted. He would then be sent to the Work Brigade Camp at Jalan Bamai where he would work for six months. A detainee who broke the regulations or misbehaved on Pulau Senang would be returned to Changi Prison, at the whim and fancy of Dutton.

Fourth Stage. Finally, the detainees could be released back to society. Prior to release, the detainees not only had to have a permanent and regular employment waiting for them, but also certified to be reformed to the extent that he was “unlikely to return to gangsterism”.

With the four stages in place, the experiment was underway by 1960.

The Superintendent

In June 1960, Prisons Superintendent Daniel Stanley Dutton landed on Pulau Senang with the first 50 prisoners, all of whom he had hand-picked. Thereafter, others that followed were chosen by the Superintendent of Prisons at Changi Prison and they arrived in batches of 30.

The running of the island was supervised by the Irishman, with over 20 officers and attendants under his wing. The true personality of Dutton remains an enigma with conflicting reports about his character.

On one hand, he seemed to believe in the inherent good of men – that everyone could be saved from evil. Criminals, secret-society members, gangsters; they were all the same. “All our evils can be conquered by hard work: we can sweat the evil out of us,” said Dutton to the late British Journalist Alex Josey. He wore this belief on his sleeve during his time at Pulau Senang.

It was because of this belief that he had utmost faith in the experiment and what it represented. He was almost ludicrously trusting of it. This was despite the fact that the island was prowling with violent men, some who were even murderers.

“They don’t want to escape,” said Dutton to Josey confidently. “They volunteered to come here, to get away from the prison routine. For the first time in their lives they’ve got a steady job. There are no cells here. Everybody does a full eight hours’ work, gets twice as much grub as they would in jail and goes to bed healthily tired”.

Other accounts of Dutton result in a caricature of a harsh disciplinarian. His iron-fist style meant that he subjected his prisoners to extremely harsh disciplinary methods. Dutton was known as the ‘Laughter Tiger’ on the island, a name that paid homage to how he was regarded by others.

It was also revealed that he had blatantly disregarded a 44-hour work week rule in the experiment’s initial years. Under the Criminal Law, it was also stipulated that detainees would not work on Saturday afternoons or public holidays. In the beginning, Dutton’s “tremendous drive and ambition” had made the men work 12-hours per day, all whilst being paid only $0.10 for their work. It was only later in March 1961 that their pay was raised to $0.30.

There were also rumours that Dutton had forced prisoners to donate blood when the Blood Transfusion Unit came, with the ultimatum that they would be sent back to Changi if they did not. This accusation came with how the detainees had won a prize for being the organization with the greatest number of blood donors of the month.

“That is diabolical truth,” refuted Major James.

Whether it was Dutton’s power that had gone to his head or his pious belief in hard work and salvation, it was his authority that had caused his death.

A Good Start

Dutton (2nd from L), PM Lee (with sunglasses and hat) and President Ishak (with tie, facing the camera) speaking to prisoners. (Source)

In the early stages, the experiment was thought to be a success. People who used to be from rival gangs now worked shoulder to shoulder in the sun and rapport strengthened as they heaved and ho-ed in unison.

Though initially known as a “virgin jungle” for its barrenness, Pulau Senang was quickly transformed into a penal settlement. Everything that was on the island was built from scratch by the detainees. They were tasked to build their own dormitories, amenities and infrastructure on the island. Some cultivated vegetables and reared livestock. It was quite literally a city that ran on its own; it had reservoirs, educational facilities, recreational facilities and even a sports ground.

“A good start,” Prime Minister Lee Kuan Yew had commented when he visited the island in November 1961. The progress that had been made was astounding: two fifty-bed dormitories, a two-acre vegetable farm and a generator had been built among many others.

In less than two years, 255 tough criminals passed through Dutton’s care, with only 23 reoffending. A great majority had been reabsorbed into society. Local press was singing generous praises of its success – “an island with more ups than downs” read a headline, “mercy pays a profit”, read another. Nair was elated with the results, proudly claiming that the “social therapy of Pulau Senang makes the island one of the most successful penal experiments anywhere in the world”.

For all its success, not all detainees were pleased with their stay in Pulau Senang. Over the course of time, there had been multiple escape attempts. It was near impossible, however, given that the island was surrounded by shark-infested waters and powerful currents.

Pride Before a Fall

The jetty being constructed. (Source)

All went askew when Dutton signed his own death warrant on 9 July 1963. On that day, he had instructed 13 carpenters to work on a 400-foot jetty on a Saturday afternoon. They had refused, and Dutton had ordered them back to Changi Prison for their disobedience.

Major James later explained that the building of the jetty was dependent on the state of the tide that ran between Pulau Senang and its neighbouring island, Pulau Pawai. As a result, it became necessary to work on it during odd hours when the tide was low.

On 10 July, a death-list of six prison officers was drawn up by the leaders of the riot. Tan Kheng Ann, one of the said leaders, said that Dutton had headed the list. When Dutton was warned of the list, he scoffed.

“He said he was not afraid. Anyone who attacked him would land himself in hospital for a week. One punch would be enough,” said Chong Sek Ling, the informant. When asked why he had helped Dutton, Chong said, “Because during my three years at Pulau Senang, I found Dutton was not corrupt. He was fair. He gave equal treatment to all,”. He also admitted that detainees confided in him as they had an affection for him.

On 11 July, Major James had heard of the plot and decided to go over to Pulau Senang. He told Dutton that he was “ill-advised” to send the carpenters back to Changi Prison, to which Dutton replied that he would “probably send them back to Pulau Senang within a reasonably short space of time”.

The Riot

The island after the riot. Destroyed dorms (below) and the jetty which caused it all (above).

Come 12 July, destruction fell upon the island.

12:40PM. After lunch, a start-work gong struck. Armed with cangkuls and parangs, the detainees start on their gardening task.

Major James is informed that Dutton wanted him urgently on the radio. “There is a rumour here that there is going to be trouble, that they are out to get me,” said Dutton. He assures that all was in control; ringleaders had been arrested and he was trying to contact the Marine Police. Major James says he will get in touch with the police.

“That is not necessary,” insists Dutton.

Major James phones the police anyway and informs Dutton to expect their arrival at about 2:00PM. He instructs Dutton and his staff to leave the island should there be trouble.

“Good God! There is no need for that,” exclaims Dutton. “There are always plenty of them who will stand by me,”.

12:50PM. Upon an arranged signal, a mob marches up to the authorities, armed with cangkuls, parangs, pipes and other weapons. Some attacked the warders, while others made for the radio room where Dutton and his chief officer, J.W. Tailford were stationed at. Both had neither armoury nor firearms on the island for protection.

“Fellow sufferers! Pulau Senang is not going to be a success! We have been here for 30 months and we are still here! Join us!” bellowed one rioter. The warning siren blares on helplessly.

1:12PM. The Marine Police receive three frantic calls from Dutton. The situation had escalated and it was spiralling out of control. “Situation very bad. Please inform Coast Guard.”

1:14PM. Lance Corporal Abdul Aziz bin Saji is notified of the rioting at Pulau Senang. All marine officers at sea and a police boat are called for reinforcement.  

3:45PM. Major James arrives at the island aflame. All rioters had been rounded up and he is told that Dutton, along with two others, were dead. They had already been when the riot squad arrived.

The Aftermath

Pulau Senang rioters arrive at the Criminal District Court. (Source)

71 detainees were charged with four counts of murder, one of attempted murder and one of mischief of causing fire. Of the 71 men, 59 stood trial before Justice Murray Buttrose on 18 November 1963. It was the largest trial Singapore had seen yet and lasted 64 days.

During the trial, it was questioned what the true intention behind the mutiny was. Was it a protest against authority, or a protest against the experiment?

“The conditions on the island were such that they were being slave-driven, driven like beasts rather than human beings? It was the injustice and unfair treatment they were receiving that brought about this incident?” questioned Mr A. J. Braga, a lawyer of three of the accused.

Major James had denied this accusation, claiming that the detainees had looked happy and healthy when he visited the island. Josey had echoed this sentiment. Instead, Major James attested to Dutton’s kind nature and blamed it on the rioters’ loutish desire for freedom.

“Dutton had to be, had the misfortune to be, the living embodiment of a system affecting their lives on Pulau Senang. He represented the authority of the Singapore government and in my opinion, that holocaust was directly directed against the Singapore government and the system that detained them,” replied Major James.

Many others have theorized why the experiment had failed. The late Professor Tom Elliot had surmised that the very success of the experiment had led to its downfall. With the island running like a well-oiled machine having “passed the pioneering stage”, it allowed time for “discontent, complaints and conspiracy”. Ideally, he said, the experiment would have truly succeeded if there had been several islands to be worked on.

Josey, on the other hand, believed that the macabre series of murders and destruction was an attempt by the secret societies’ leaders to “prove publicly that they, not Dutton or the government he represented, controlled their members”.

Eventually, 30 were found guilty of rioting and rioting with deadly weapons, and 18 were sentenced to death. They were charged with the murder of Dutton and his two assistants, together with the destruction of the island.

PM Lee visiting injured wardens. (Source)

The attack on Dutton had been animalistic. His entire body was maimed with cuts; three on his head, two on the trunk, nine on the limbs. His fifth, ninth and tenth ribs were fractured. His body was completely burnt, except his feet which were covered by his boots.

Within 40 minutes, the same hands that built the island had completely annihilated it. It was estimated by Major James that the total damage was worth a whopping $500,000.

The judge delivered their sentence: “The time has now come for you to pay the penalty for your dreadful acts… the sentence of the court upon you is that you be taken from this place to a lawful prison and thence to a place of execution and that you be hanged by the neck until you be dead and may the Lord have mercy on your souls”.

On 29 October 1965, the men breathed their last breaths.

Why Did the Experiment Fail?

It was not until 1968 that Pulau Senang was officially declared no longer a penal island. It was out of bounds for many years until 1984, when the island was (and is) recycled as a Live Firing Area by the Singapore Military.

Ever since the massacre, Singapore hasn’t gone back to a prison-without-bars.

On the contrary, other countries have taken to this method. On an island just 10 minutes away by boat from Norway sits the Bastoy Prison, otherwise hailed “the world’s nicest prison”. Prisoners did menial work, were offered high-quality education, and lived like villagers. Not only had there been neither a murder nor a suicide on the island, it also carried the lowest reoffending rate in Europe at 16% to its name.

Before it became what it was today, the island was used as a juvenile detention center. It later met the same fate as Pulau Senang when it became an insurrection. The rebellion by the boys constituted a series of attempted escapes, refusal to work, and arson. Yet the failure of the centre had not derailed hope for the Bastoy Prison.

Finland’s Ojoinen open prison is based on the same belief that the system of self-sufficiency could likewise reduce the risk of recidivism. In fact, inmates have it so good that one even likened it to “living in a holiday camp”.

Though these open prisons and the experiment Pulau Senang seem to be similar, both were starkly different at its core. While the former emphasized comfort, the latter emphasized hard work.

“It was never intended that Pulau Senang should be a holiday camp for tired businessmen, nor yet a picnic island for school boys and university student on holidays,” said Major James. “It was a prison settlement,”. Dutton believed the same – Pulau Senang was not built to be enjoyed.

What did they do right and where did we go wrong?Till this day, the question as to why the experiment failed still remains unanswered. Maybe it could have been avoided if Dutton hadn’t been so hard on the prisoners. Maybe blind faith shouldn’t have been placed on criminals. Maybe defensive firearms on the island would have helped.

Maybe, maybe, maybe.


Gracia Koh


In a world that is bubbling with clickbait, sensationalism and oversimplifications, Kopi aims to bring long-form journalism back to South-East Asia.

Through deeply analysed articles, we uncover and explain the complex and multifaceted issues facing our societies. Through engaging narratives, we tell stories that are bold and unique.

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