John Boysie Singh was born on 5 April 1908 in Woodbrook, Port of Spain, Trinidad. He was the son of Bhagrang Singh, a Punjabi fugitive from British India who had immigrated to Trinidad. Growing up in a colonial society marked by sharp divisions of wealth and opportunity, Boysie gravitated toward the underworld early in life.

By the 1930s, he had already developed a reputation as a gambler and petty criminal. His first major brush with the law came when he was charged with breaking and entering. This nearly resulted in his deportation from Trinidad, but Boysie successfully fought the charge, strengthening his reputation as a man who could outwit the system.

As he matured, Boysie transformed into a flamboyant gangster. In the streets of Port of Spain, he was known for his bright, stylish clothing and his swaggering walks through public spaces.

Boysie Singh’s reign of terror as a pirate and murderer began in earnest in 1947. For nearly a decade, until 1956, he and his gang operated in the waters between Trinidad, Tobago, and Venezuela. Their method was both cruel and effective. They would lure unsuspecting passengers with promises of ferrying them to Venezuela which is often migrants seeking better opportunities or travelers unaware of his reputation. Once out at sea, the gang would rob the passengers at gunpoint, then murder them. Victims were shot, stabbed, or bludgeoned before being dumped into the Caribbean Sea.

Estimates suggest that as many as 400 people lost their lives to Singh’s maritime massacres. Despite the staggering scale of his crimes, he proved remarkably elusive in the courts. His ability to intimidate witnesses, manipulate the system, and instill fear across communities made convictions almost impossible.

Throughout the early 1950s, he walked the streets of Port of Spain like a man above the law. Locals both feared and gossiped about him, and his notoriety grew into legend. He was called “The Raja”, a Hindi word meaning “king”, symbolizing his dominance over the underworld and the waters of Trinidad.

His downfall finally came not from the sea, but from a murder on land. In the mid-1950s, Singh was charged with killing Hattie Werk, a dancer, and with murdering his own niece. The latter trial ended in acquittal, but the Hattie Werk case proved his undoing. With mounting public pressure and enough evidence presented, Singh was convicted of murder in 1957.

On 20 August 1957, at the age of 49, John Boysie Singh was executed by hanging in Port of Spain.