The Pulau Senang riots was a case of armed rioting and murder that happened at the Singaporean island of Pulau Senang, where a reformative prison settlement was operated by the government of Singapore to imprison and rehabilitate secret society members, as well as to avoid prison overcrowding at Changi Prison. The settlement first opened in 1960, and had seen bouts of success in reforming many gang members and allowing them to rejoin society.

On 12 July 1963, about 70 to 90 out of the island prison's 300 detainees staged an uprising, resulting in a riot that devastated the whole settlement and killed four prison officers - consisting of Prisons Superintendent Daniel Stanley Dutton, and three of Dutton's assistants Chok Kok Hong (), Tan Kok Hian () and Arumugam Veerasingham. Several others, including prison officers and some of the detainees who refused to join the riot, were also injured, but later survived. At the end of the riots, police reinforcements and the Marine Police arrived at Pulau Senang to arrest the rioters, with 71 of them being charged with murder.

In an unprecedented 64-day trial ever conducted in the history of both Malaysia and Singapore, 59 rioters were brought to trial for four charges of murder, with both a special jury of seven and the veteran judge Murray Buttrose set to hear the case. Eventually, eighteen of the defendants, including the ringleader Tan Kheng Ann (alias Robert Black; ) were sentenced to hang for the murders while another 29 rioters were jailed between two and three years for both rioting and aggravated rioting with deadly weapons, and the remaining twelve defendants were acquitted of all charges.

Background In 1960, an experimental-type offshore penal colony was established on Pulau Senang by the Singapore government, after the proposal was made by former political prisoner and future president Devan Nair. On the island, the secret society members were allowed to roam freely and were put to manual labour, as part of a rehabilitation programme to allow them to rejoin society. The settlement was established as a countermeasure to resolve the issue of prison overcrowding, as attributed to the large number of suspected gang members being arrested and detained without trial per the government's tough crackdown on secret societies in Singapore.

The prison-settlement was started on 18 May 1960, when about 50 detainees, sent from Changi Prison, arrived with Irish-born Prisons Superintendent Daniel Stanley Dutton, the appointed chief of the penal settlement; another 20 officers and attendants were appointed to the island. Over the next three years, the number of detainees from the mainland rose to 320 and together they transformed the island into an attractive settlement, and there were bouts of success from the results. By September 1962, about 200 offenders had been deemed sufficiently rehabilitated and suitable to return to society.

Dutton was known to be a largely benevolent and lenient leader of the island prison, as he believed that not all humans are born evil and believed that reformation is possible for them through hard work. He also did not allow guards to carry arms as part of the need to build trust between the guards and inmates. However, despite such an outlook, he was also a strict enforcer of discipline and would not tolerate any rule-breaking or defiance of orders from any inmates, and often harshly penalized those detainees who broke the rules. Hence, while he was held in high regard by many detainees and guards, he also earned an unfavourable opinion and dislike from others. Also, the abuse of detainees by some of the prison wardens add to the displeasure the detainees harboured against the authorities who operated the Pulau Senang settlement.

Out of the detainees, Dutton shared the closest bond with Tan Kheng Ann, a high-ranking member of the underworld and one of the few gang members who was English-educated. Tan, also known as Robert Black or Ang Chuar (meaning "Red Snake" in Hokkien and so-named due to his birth in 1941, the year of the Snake), was said to be a charismatic man who mixed well with others and deeply trusted by Dutton. However, when the riots happened on 12 July 1963, Tan was ironically the ringleader who led more than 70 detainees to kill Dutton and cause a revolt.

Prison riot and killings

On the afternoon of 12 July 1963, after lunchtime, the guards escorted the 320 detainees to their workplace, where they would carry out their work as usual according to their routine.

It was at this point, about 70 to 90 detainees, armed with parangs and changkols, began to attack the prison guards, as well as the other detainees who refused to join the riot, which lasted for forty minutes and led to a severe destruction of the settlement on Pulau Senang. During the unrest, 39-year-old Daniel Stanley Dutton escaped to the radio room, where he called for help, calling for the assistance of the Marine Police. However, soon after sending the distress signal, Dutton was attacked by the rioters, who poured petrol on him and set him on fire, and he was subsequently slashed and chopped to death by the rioters, who mutilated his body. Three other prison guards - Arumugam Veerasingham, Chok Kok Hong and Tan Kok Hian - were also killed by the rioters in midst of the uprising. Several other people, including Deputy Superintendent John William Tailford, were grievously hurt but they later survived with timely medical intervention. According to Low Ah Kok, a settlement guard, the hospital and petrol station on Pulau Senang was not spared from the damage inflicted by the rioters.

Later, police reinforcements arrived at Pulau Senang, and they all arrested the rioters, who were seen dancing and singing in rejoice at their spoils and destruction of the settlement. Prior to the arrival of the police, one of the rioters Tan Yim Chwee (later known as Accused No. 27; ), whose shirt was stained in Dutton's blood, used it as a flag mast per their celebration of succeeding to kill Dutton. The arrested rioters were all charged with rioting and murder.

Trial proceedings Selection of jury and lawyers of trial On 18 November 1963, after several preliminary hearings, about 59 alleged rioters stood trial at the High Court for the murders of Dutton and three other guards. The number of accused was reduced from 71 to 59 after the preliminary hearings ended with the discharge of 12 defendants from the case.

Till today, the trial was known to be the largest ever conducted in the legal history of both Singapore and Malaysia (since Singapore was still a part of Malaysia at the time of the trial), given that there was a high number of defendants being charged with murder. For easier identification, the 59 accused were to wear number tags: the ringleader Tan Kheng Ann was labelled as Accused No. 1, while his two trusted henchmen Chia Yeow Fatt (alias Botak; ; Pha̍k-fa-sṳ: Chhia Yû-fat) and Cheong Wai Sang (alias See Jap Kau Sian; ), who were also among the principal perpetrators of the riot, were labelled as Accused No. 2 and 3 respectively. A special courtroom dock was designed to accommodate the 59 defendants.Public Prosecutor v Tan Kheng Ann and Others (1964), High Court (Singapore).

The trial prosecutor was Francis Seow, who was notable for prosecuting law student Sunny Ang and bar hostess Mimi Wong for murder. The trial judge was Murray Buttrose, who was best known for sentencing the aforementioned killer Sunny Ang to death for killing his girlfriend. A special jury of seven members was selected to hear the case, and back then in Singapore, jury trials were conducted to hear capital cases up until 1970, before the abolition of the jury system.

Prosecution's case Major Peter James, a retired British army officer and director of the Singapore Prison Service, testified that he received a phone call from Dutton on the morning of 12 July 1963 before the riots happened, and he stated that Dutton told him there were signs of people who wanted to oppose him, but despite Major James' concern and his pressing demands for a reserve unit to be dispatched to Pulau Senang, Dutton maintained that there was no need for reinforcements, as he was assured that a majority of the detainees would be at his side. However, James went ahead with the dispatch of the reinforcement, but it was too late since the riots had happened. Although the nine defence lawyers of the rioters accused Dutton of torturing and oppressing the detainees into working overtime and became a slave driver who abused his authority, Major James defended Dutton and stated that Dutton was the "kindest of men" he ever knew, and that he was a naturally born leader whom he felt suitable to run the island. Allen Tan Kiat Peng, a detainee who was serving the remainder of his seven-year sentence for robbery on Pulau Senang, stated that the treatment of the detainees were generally "okay" and there was little to no abuse coming from the officers, despite conceding that there was indeed excessive workload on the island.

Chong Sek Ling, a former gang leader who spent time on Pulau Senang, testified that after an event in July where thirteen carpenters were sent back from Pulau Senang to Changi Prison due to their refusal to repair a jetty during nighttime, he overheard more than ten high-ranking gang leaders discussing about their plan to kill Dutton and the other officers of the settlement, due to their dissatisfaction of the treatment they faced and hatred against Dutton for his supposed iron-fist rule and discipline. Among these people, Chong identified Dutton's closest friend and detainee Tan Kheng Ann, Tan's two henchmen Cheong and Chia, and Hoe Hock Hai (alias Ah Hai; Accused No. 11; ; Pe̍h-ūe-jī: Hôu Hok-hái). Chong stated that he warned Dutton about the upcoming murder plot, but Dutton, whose nickname was "Laughing Tiger", laughed it off and thought that it would not be a big threat on his life even if there was such a conspiracy, although he did ask for the names of the ringleaders. According to Chong, Hoe remarked during their discussion that this unrest would shake the whole of Malaya (present-day Malaysia).

Chong further testified about what he witnessed on the day when the riots happened. One of the things he saw while hiding in the forest was some of the rioters going after Goh Keng Wah (alias See Kar Chua or monitor lizard in Hokkien), a detainee who was an informant of the guards. Goh tried to seek help from Corporal Choo Ah Kim, who was subsequently beaten by the guards despite managing to help Goh escape. During the assault, Corporal Choo was saved by another detainee Quek Hai Cheng, who shielded the blows aimed at the officer, who also confirmed Quek's actions during the preliminary hearing. Liew Woon, another former detainee, also said that he saw two of the defendants – Chan Wah (Accused No. 9; ) and Sim Hoe Seng (Accused No. 25; ) – climbing the roof of the radio room (where Dutton was using the radio to call for help), chopping through the roof and pouring petrol before starting a fire, causing Dutton, whose body was on fire, to run out of the building, upon which the rioters killed him in a deadly assault. Tan King Hak, an engine diesel instructor of the settlement, also testified that after escaping the radio room, he saw a detainee Lim Tee Kang (Accused No. 5; ; Pe̍h-ūe-jī: Lîm Tsì-khang or ; Pe̍h-ūe-jī: Lîm Tsì-kang) cutting the wires of the radio with an axe as he and three other rioters Lim Kim Chuan (Accused No. 7; ), Ponapalam Govindasamy (Accused No. 12) and Ng Cheng Liong (Accused No. 26; ) surrounded the burning radio room to prepare their fatal attack on Dutton (who was still inside).