Carrera Island: The history of Trinidad and Tobago’s notorious prison island

Off the north-western coast of Trinidad, nestled in the Gulf of Paria near Chaguaramas, lies a rugged limestone islet shrouded in legend and history, Carrera Island. Known today primarily as a penal colony, the island’s storied past is far more complex than its present use as a prison.

From its early roles as a quarantine station and medical facility, to its transformation into a symbol of colonial punishment, Carrera Island has long been associated with isolation, control, and the brutal realities of justice in Trinidad and Tobago. This article traces the evolution of the island from its 19th-century beginnings to its status in the modern era, spotlighting some of its most notorious inmates and the infamous stories that continue to echo across its stone walls.

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From healing ground to prison island

The earliest known use of Carrera Island was not as a prison, but as an auxiliary ulcer hospital to the overcrowded Colonial Hospital in Port-of-Spain in the mid-1800s. Rooted in Victorian medical theory, particularly the belief in miasma or “bad air” as the cause of disease, authorities saw the island’s breezy, isolated environment as ideal for healing.

A legislative council member in 1866 even noted that ulcer patients had “already derived a boost from the pure air and sea bathing”. That same year, there were proposals to use Carrera as a convalescent station for Indian indentured labourers upon their arrival to Trinidad, though it was ultimately Nelson Island that was selected for this purpose.

However, by 1854, the island had already started transitioning into a punitive space. Daniel Hart, then Superintendent of Prisons, began housing convicts on the island to work on what would become Hart’s Cut, a man-made canal across the Chaguaramas isthmus. Carved entirely by convict labour under harsh conditions, the canal was completed in 1856 and provided a vital shortcut, sparing sailors from navigating the treacherous waters off Point Gourde.

By 1875, Carrera Island’s fate as a penal colony was cemented. Prisoners were set to work “bussin’ stone” from the island’s limestone formations, providing materials for public infrastructure while enduring severe conditions. Meals consisted of little more than biscuits, tea, and a pint of watery soup, and punishment was unrelenting. The idea was simple and brutal: deterrence through suffering. This concept was drawn from England’s Criminal Law Act of 1776, which emphasised hard labour as a core part of incarceration.

The stone fortress: Establishing Carrera as a penal colony

Construction of the main prison complex began in 1876 and was completed by 1880, using labour from prisoners transferred from timber depots in Longdenville and Irois Forest. The facility, enclosed by formidable stone walls, became a fortress of discipline and reform under successive prison superintendents. One of the most notable was Captain Percy Fraser, who led the institution well into the early 20th century and viewed punishment as a pathway to moral reformation.

During World War I, prisoners from Carrera were even put to use in national defence, hauling heavy artillery up steep hills on neighbouring Gaspar Grande Island under the watchful eyes of Capt Fraser and then-Governor Sir John Chancellor. Despite its austere environment, the prison began offering limited reforms, including adult literacy classes, vocational training, and film screenings—though these improvements were often undermined by the sheer brutality of daily life.

The darkness within: Horror stories and notorious inmates

Carrera Island gained an almost mythical reputation for the grim tales emerging from its cells. One of the most shocking involved a wave of self-inflicted blindness among Indian prisoners in the early 20th century. Lured by a rumour that blind inmates would be released and returned to India for treatment, prisoners crushed crab bile into their eyes, causing irreversible damage in the hope of freedom.

Another grotesque tale involves a prisoner convicted of a sexual offence who amputated his own testicles in secret, hoping to prove remorse or gain sympathy. These relics were preserved in alcohol in the prison infirmary—a macabre symbol of the desperation endured by those incarcerated.

One of Carrera’s most infamous inmates was Boysie Singh, perhaps Trinidad’s most legendary gangster. Born in Port-of-Spain, Boysie rose to infamy in the 1940s and 50s as a gambler, extortionist, and later, pirate and mass murderer. He and his gang terrorised the Gulf of Paria, robbing and killing those aboard inter-island vessels. Convicted for the murder of a woman, Singh was hanged in 1957 after a trial that captured the national imagination. His time on Carrera remains one of the island’s darkest associations.

Other notable prisoners included:

Alphonso Dyer, convicted in the 1920s for a string of armed robberies and multiple murders across central Trinidad. Known for his charisma and cunning, Dyer repeatedly escaped custody until finally being apprehended and sent to Carrera.
Roy “Blanco” Carter, a notorious gang leader from Laventille in the 1960s who was sentenced for armed robbery, kidnapping, and attempted murder. His reign of terror contributed to a national crackdown on gang activity.
Harold “Stickman” Rawlins, convicted in the 1970s for multiple home invasions and the brutal assault of several victims in north Trinidad. His capture led to heightened security measures at the island prison.
“Cutty” Joseph, a feared contract killer during the 1980s, linked to the underworld dealings of cocaine trafficking. He was convicted of first-degree murder and conspiracy to commit murder.
Trevor “Snakeman” Williams, imprisoned in the 1990s for drug trafficking and racketeering. Williams orchestrated a failed escape attempt by building a makeshift raft and trying to paddle the shark-infested waters—a futile but daring bid that ended in capture and solitary confinement.

A Caribbean Alcatraz: The fear and lore of Carrera

Carrera Island is often compared to Alcatraz, not just for its isolated geography but for its symbolic weight as a place of no return. The phrase “Abandon hope, all ye who enter here” could easily apply. Floggings with the cat-o’-nine tails, bread-and-water rations, and confinement in sewage-filled cells made Carrera a place feared by all.

Yet, for the officers stationed there, the experience was paradoxical. Eulick Bissessarsingh, father of historian Angelo Bissessarsingh, served on Carrera during World War II and often spoke of the strange kinship between jailers and prisoners during the long tours of duty. With weeks-long stints on the island, even the wardens felt the burden of isolation.

Resistance and reform

Not all inmates accepted their fate passively. Over the decades, several escape attempts have been made. Despite the strong currents and sharks that populate the channel between Chaguaramas and the island, desperate men still tried to swim to freedom. Few succeeded.

In 1931, a major prison riot led to warders being taken hostage. The crisis was diffused only after Capt Fraser personally intervened. This incident led to a Commission of Enquiry, which recommended significant reforms. The prison’s infrastructure was improved, and some humanitarian programmes were introduced, but the legacy of brutality endured.

Modern Day: The island that refuses to close

In 2013, the Government of Trinidad and Tobago announced plans to decommission the prison. Yet as of 2025, Carrera Prison remains operational, a relic of colonial justice still clinging to life. It continues to hold some of the nation’s most dangerous criminals, and the public perception of it remains unchanged—an isolated fortress where society’s worst are cast away.

Although off-limits to the general public, the island remains an object of fascination. The National Trust of Trinidad and Tobago offers Western Isles tours that explore the history of Carrera and surrounding islets like Nelson and Gaspar Grande. These tours provide a rare glimpse into the mysteries of the “Devil’s Island of the Caribbean”.

A mirror to our justice

Carrera Island is more than just a prison; it is a living symbol of Trinidad and Tobago’s evolving relationship with justice, punishment, and power. From its days as a healing outpost to its feared reputation as a penal colony, Carrera has absorbed the traumas, violence, and resilience of generations.

Today, as debates continue over prison reform and the ethics of incarceration, Carrera stands as both a cautionary tale and a historical monument. Its enduring presence urges us to confront the past—even the darkest parts—and to question the legacies we inherit.

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Question & answer:

Q: What is Carrera Island known for in Trinidad and Tobago?
A: Carrera Island is known as Trinidad and Tobago’s most infamous prison island, historically used to house the country’s most dangerous criminals. Located off the coast of Chaguaramas, it has served as a penal colony since the 19th century and remains operational today.

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