How The Kray Twins Ruled The Underworld Of Swinging Sixties London In Style

Published April 9, 2019
Updated May 22, 2023

The Kray brothers Ronnie and Reggie may have owned dozens of nightclubs and hobnobbed with celebrities, but they also committed some of the most shocking murders gangland London had ever seen.

Kray Twins

TwitterThe Kray twins, Ronnie and Reggie, in 1966.

Ronnie and Reggie Kray, better known as the Kray twins, remain perhaps the most infamous criminals in London’s rogue’s gallery of gangsters throughout history. During the 1960s, they ruled the streets of London’s rough-and-tumble East End.

And while some crime lords kept their heads down and went about their business, the Kray Twins never kept a low profile as they carried out everything from armed robberies to arson while hobnobbing with politicians and celebrities — as portrayed in the 2015 film Legend — before they were finally brought to justice.

The Early Years Of The Kray Twins

Ronnie and Reggie Kray were born within ten minutes of each other on Oct. 24, 1933, in Hoxton, London. From a young age, the twins had an insatiable desire to become somebody.

Ronnie And Reggie Kray

Facebook17-year-old Reggie (left) and Ronnie (right) with their mother, Violet Kray in 1951.

Like their grandfather Jimmy “Cannonball” Lee before them, the Kray brothers got their schooling in taking and giving a beating early on when they took up boxing. Both became amateur champions and were said to have never lost a fight.

Meanwhile, they displayed some of the differences in character that would inform their future lives as criminals. Reggie was a calmer, more disciplined boxer, while Ronnie showed early signs of his rabid desire to win no matter the cost.

And soon, the Kray twins took their fighting into the streets — and got themselves into trouble. They started getting involved in gangland activity on the streets of the East End.

At 16, the cops charged them with grievous bodily harm after they attacked a rival gang outside a dance hall.

Two years later, in 1951, they spent a month in prison for assaulting a police officer while also acting so violently and rambunctiously — including dumping a latrine bucket on a sergeant and setting their own beds on fire — that they were dishonorably discharged from the army soon after being conscripted.

Kray Twins Boxing

FlickrThe Kray brothers in boxing gear as young men.

But soon, they would take their criminal activities to even greater heights. While making a name for themselves thanks to armed robbery and hijacking, they also got into the nightclub business, starting out by turning a small, rundown club in Bethnal Green into a respectable joint. And so they started their ascent of the London underworld.

Ronnie And Reggie Kray: Kings Of Gangland London

The Kray Brothers

TwitterThe Kray twins were equal parts celebrity and gangster.

As up-and-coming gangsters, the Kray brothers had a particular role model: the stylish “boss of Britain’s underworld,” Billy Hill, who controlled Soho in the 1950s. Hill lived a jet-setting lifestyle in southern France and Morocco.

Like Hill, the Kray twins bought and paid for their more legitimate businesses with the proceeds from their criminal activities. As they expanded into protection rackets, arson, armed robbery, and sales of black market cigarettes, they also expanded their nightclub empire by purchasing a string of clubs in the East End as well as central London.

But despite a semi-legitimate approach to making money, violence was still integral to how they operated. While both were capable of extreme violence, Ronnie’s angry flare-ups grew uncontrollable. In 1954, members of a Maltese gang tried to collect protection money from the twins in their newly acquired Regal Billiard Hall. Ronnie’s response was to attack them with a cutlass.

But to legitimize their appearance despite their criminal activities, the Ronnie and Reggie Kray maintained an elaborate façade via organizing donations to charity.

But Ronnie’s mental instability began to erode any notion of their respectability. In 1956, he received three years in prison after slashing and stabbing a man with a bayonet and then beating him unconscious.

While Ronnie was away, Reggie developed their business and criminal interests. In 1957, he opened the Krays’ signature club, the Double R, and established their gang called “the Firm.”

Tom Hardy as both Ronnie and Reggie Kray in a scene from the 2015 film Legend.

Meanwhile, in prison, Ronnie soon fell into prison psychosis. In 1958, he transferred to an asylum in Surrey, where doctors diagnosed him as a paranoid schizophrenic. After he responded well to drugs, Ronnie went back to prison. 

Upon his release later that year, Ronnie no longer bore an identical resemblance to Reggie. Prison and his condition took its toll on this member of the Kray twins. He became thickset in face and body and was more prone to unstable outbursts.

Rulers Of Swinging Sixties London

Early Mugshot Of The Kray Twins

TwitterEarly mugshots of the Kray twins.

With Ronnie out of prison and their gang established, the Kray twins became criminal celebrities who owned around 30 popular nightclubs. In his autobiography, My Story, Ronnie recalled:

“They were the best years of our lives. They called them the swinging sixties. The Beatles and the Rolling Stones were rulers of pop music, Carnaby Street ruled the fashion world… and me and my brother ruled London. We were fucking untouchable.”

With their network of nightclubs established, the Kray brothers were in their element and free to be who they wanted to be.

In 1959, the Kray twins acquired Esmeralda’s Barn, a club in the West End. Ronnie felt more comfortable being open about his bisexuality in this part of London. Soon he began hobnobbing with a number of high-society gay men that included politicians, actors, and businessmen.

Apparently (accounts vary), both twins were bisexual, though Ronnie identified more as gay and Reggie more so exhibited interest in women. In 1960, Reggie started a relationship with Frances Shea, the sister of Firm member Frank. Though Ronnie despised Frances, he became Reggie’s best man at the wedding five years later.

The Kray twins in a scene from 2015’s Legend, starring Tom Hardy as both Kray brothers.

Ronnie’s love life, meanwhile, didn’t proceed so smoothly. The Kray twins’ friends included influential Conservative Lord Boothby. Scotland Yard became aware of a relationship between Ronnie and Boothby and developed a dossier on the pair. By the summer of 1964, authorities planned a major operation against them. 

But when the gay vice scandal (homosexuality was a crime in 1960s Britain) between Ronnie and Boothby broke in the Sunday Mirror, Boothby threatened to sue the newspaper. The paper backed down, and after a £40,000 out-of-court settlement, newspapers buried any further stories linked to the Krays.

The Kray Brothers And The American Mafia

For years, Ronnie dreamed of turning the Kray twins’ empire into a version of the New York Mafia’s infamous killing factory known as Murder, Inc. And in the 1960s, he got his wish. The American Mafia advised Ronnie on how to adopt its principles for London gangs, and an important trans-Atlantic criminal alliance was born.

But this connection with the Mafia ratcheted up tensions with the Richardson gang, also prominent in London. The Kray twins wanted to expand their gambling interests in the West End with the Mafia’s help, but Ronnie felt the Richardson gang was beginning to encroach on their turf. To make matters worse, George Cornell, a Richardson henchman, called Ronnie a slur at the Astor Club in Dec. 1965. A gang war broke out, with two attempts made on Ronnie and Reggie’s lives.

Things escalated in March 1966, when someone killed Dickie Hart, one of the Firm’s members, in a shootout and Cornell was believed to be responsible. He disrespected the Kray brothers further a month later while he was having a drink on the Krays’ turf in Whitechapel. On March 9, 1966, an incensed Ronnie entered the pub and shot Cornell in the head right in front of everyone.

Reggie Kray

Wikimedia CommonsReggie Kray (second from left) in 1968.

Though the cops arrested Ronnie, intimidation from one of The Firm’s goons ensured that no one snitched on him. The barmaid was asked to identify Ronnie in a lineup but she claimed she had no memory for faces. Ronnie walked free.

A year later, Reggie too would be in trouble for murder. Though they kept evading justice, the Kray twins’ downfall was on the horizon.

The Kray Twins’ Trial And Incarceration

By 1967, Reggie’s two-year-old marriage became fraught with difficulties. In her diary, Shea claimed daily drunken, verbal abuse, and in the end tried to get her marriage annulled because it was never consummated. On June 7, feeling trapped in the couple’s Marble Arch flat, Shea committed suicide via a drug overdose.

The resulting emotions may explain why Reggie murdered Jack “The Hat” McVitie after McVitie failed to kill Leslie Payne, the Kray twins’ financial adviser. They originally intended to just “rough up” McVitie at a party in northeast London. First, Reggie tried to shoot him but the gun jammed, and after a struggle, an associate held McVitie down and Reggie killed him in brutal fashion, stabbing McVitie in the face, stomach, and chest before impaling him through the throat to the floor with a carving knife. No one ever found McVitie’s body.

The murders were the turning point in Scotland Yard’s ongoing investigation into the Ronnie and Reggie Kray. Under more pressure than ever, members of the Firm finally began to snitch on the twins. On May 9, 1968, the police arrested both Krays at their mother’s flat. A year later, they received life behind bars for the murders of Cornell and McVitie.

Grave Of Ronnie And Reggie Kray

FlickrThe grave of Ronnie and Reggie Kray.

Even in prison, though, they never strayed from their scheming ways and operated a bodyguards-for-celebrities business from behind bars, with Frank Sinatra reportedly one of their clients.

Ultimately, Ronnie died of a heart attack in March 1995, aged 61. In 2000, Reggie was released on compassionate leave after being diagnosed with terminal bladder cancer. Within weeks, Reggie too was dead, and the story of the Kray twins had finally come to an end.

After this look at Ronnie and Reggie Kray, read up on the Teddy Boys who terrorized 1950s England. Then, discover the stories of history’s most famous gangsters.

Daniel Rennie
Daniel Rennie is a freelance writer residing in Melbourne, Australia.