Kray Twins ( 1933 – 1995), UK Crime Bosses

b. 24 October 1933
d. 17 March 1995 (Ronnie) / 1 October 2000 (Reggie).

Ronald "Ronnie" Kray and his twin brother Reginald "Reggie" Kray were the foremost perpetrators of organised crime in London's East End during the 1950s and 1960s. Ronald, commonly referred to as Ron or Ronnie, most likely suffered from paranoid schizophrenia. The Krays were involved in armed robberies, arson, protection rackets, violent assaults including torture and the murders of Jack "The Hat" McVitie and George Cornell. As West End nightclub owners, they mixed with prominent entertainers including Diana Dors, Frank Sinatra, Judy Garland and politicians. The Krays were highly feared within their social environment, and in the 1960s they became celebrities in their own right, being photographed by David Bailey and interviewed on television.

Ronnie was definitely gay - and Reggie may have been.

During his life, Ronnie Kray was openly gay, refusing to hide his orintation from either the law or his fellow gangsters, but sometimes claimed to be merely bisexual - a nod to the disapproving social attitudes at the time.

'Ron discussed his homosexuality with only a very few people, but put simply it was a part of his nature he discovered, explored and enjoyed,' O'Leary(Kray's biographer) said. 'He was at ease with it. It did not seem to conflict with his "tough guy" image or cause him any problems on any level.'

The members of the twins' gang, known as the Firm, were overwhelmingly tolerant of Kray's homosexuality. 'Even if they objected, Ron just smiled at them and told them they didn't know what they were missing,' O'Leary said.

Guardian 

Reggie was closeted, although Ronnie often claimed his brother too was bisexual. After his death a former gang member, Bradley Allardyce, claims that he and Reggie had been  more than just good friends:

Bradley Allardyce moved to Altea, Spain, and opened a restaurant after his release from prison three years ago. He served nine years for armed robbery. He spent three years in Maidstone Prison, four cells along the landing from Reggie Kray. Kray, who died two years ago, was serving life for the murder of Jack 'the hat' McVitie. Both denied they were more than just friends, until now.

Allardyce said: "I am openly admitting for the very first time that we had a sexual relationship."Ronnie Kray was openly gay but Reggie always denied what many suspected - that he was also attracted to men.Friends of Kray consider Allardyce to be the love of his life. They spent most of their time at Maidstone in each other's company.

BBC