Ronnie Kray

As much as I love showing how inspirational the LGBTQ+ people of history can be…. they weren’t all wholesome heroes. And I’ll be the first to admit… sometimes it’s fun to write about a bad guy. And Ronnie Kray definitely fits the bill.

Ronald “Ronnie” Kray and his brother Reginald “Reggie” were born on October 24, 1933 in London. Their parents were Charles David Kray and Violet Annie Lee, they had a brother who was older than them by six years named Charles James Kray. Reggie was the older of the two — by ten minutes. At three years old, both twins came down with diptheria. They attended school, first at Wood Close School and later at the Daniel Street School. All in all, a fairly ordinary childhood.

As adolescent boys, thanks largely to their grandmother, the twins took up amateur boxing. Egged on by their sibling rivalry, they actually managed to be kind of successful at it. (Inherent violent tendencies probably helped too.) In March of 1952, the twins were called upon to join the National Service in the British Army. Although they did show up to the depot as they were supposed to, they tried to leave after only a couple of minutes. A corporal tried to stop them from leaving — Ronnie punched him in the jaw and the two kept going, walking all the way back home. The next day they were arrested — the police turned them over to the army.

That September, the twins were both absent without leave again. When a police officer tried to arrest them, the duo physically attacked him — which led to them being held in the Tower of London. This gives them the grand distinction of being among the last prisoners held in the Tower until they were transferred to a military prison. They were held there until they were dishonorably discharged — and when it became apparent that that was the inevitable outcome of their incarceration, the twins became increasingly badly behaved — their antics including dumping hot tea on a guard, handcuffing a guard to their cell bars with a set of stolen cuffs, and setting their bedding on fire. Eventually, they attacked one of their guards with a vase and escaped. They escape attempt was short lived, they were soon recaptured. After their discharge, they were transferred to a civilian prison where they served time for all of the crimes they’d committed since going AWOL.

The dishonorable discharge and the criminal records killed their budding boxing careers, so the two took their violent behavior and turned it into a full-time career in organized crime. They began by starting a protection racket, but ultimately fell in with Jay Murray and, through him, became involved in armed robberies, hijacking, and arson. Through these illicit activities, they came to own several properties.

In 1960, Ronnie got arrested for running a protection racket. While he was in prison (for 18 months), Reggie was given ownership of a nightclub Esmerelda’s Barn — which, apparently, was a really happening night club frequented by very famous people despite have “barn” in its name. Owning this not only gave them more influence in the criminal underworld of the West End, and allowed them to have a base of operations for their gang “the Firm” — but also gave them legitimate income and brought them into the social circles of celebrities like Judy Garland and Diana Dors. As celebrities, the Kray brothers were much beloved — as criminals, they were greatly feared. Even the people who worked for them could face severe and painful punishments if they disappointed or failed to show the proper respect.

In July of 1964, however, Ronnie caught the attention of tabloids for an entirely new reason: his sex life. The Sunday Mirror published an article implying that Ronnie Kray was involved in a sexual relationship with Conservative politician Lord Robert John Graham Boothby. Sodomy was, at this point, still a criminal act in the United Kingdoms. The Conservative party moved to shut down the news story — and so did their rivals the Labour party, as they sought to protect Tom Driburg — a member of parliament who was (relatively) open about being gay and frequently socialized with Lord Boothby and Ronnie. Ultimately, the Sunday Mirror settled out of court and paid Lord Boothy £40,000.

And while the scandal the entire event caused may have been potentially damaging for politicians in the UK — it did nothing but help the Kray brothers. The two became practically untouchable, as now neither the Labour or Conservative parties wanted Ronnie investigated for fear of what might turn up about the sexual proclivities of their own members. It took another two years before the Kray criminal empire began to unravel — and it didn’t really happen because of any police investigations.

Over the next two years, Ronnie began to suffer from paranoid schizophrenia. On March 8, 1966 a shootout with a rival organization called the Richardson Gang left one of their associates in the Firm, a man named Richard Hart, dead. A member of the Richardson Gang, George Cornell, who was not involved in the shooting but was known to call Ronnie some derogatory names for gay men like “fat poof”, was drinking at the Blind Beggar Pub the next day. That pub was only like a mile away from where the Kray brothers lived, so Cornell was maybe not making the best decisions at the time (but to be fair, he’d probably been drinking for a while.) Ronnie found out that Cornell was there, and had his driver “Scotch Jack” John Dickson and his assistant Ian Barrie bring him to the pub. (Side note: if your driver’s nickname is two different kinds of liquors maybe hire a different driver. I’m just saying.)

When Ronnie walked into the pub, Cornell reportedly said “Well, looks who’s here.” And then Ronnie shot him. Barrie threatened the full-on crowd of onlookers not to say anything, shot up the ceiling a bit, and then brought his boss back out to “Scotch Jack” to drive them away. Cornell died in the hospital at 3 am.

In December of that same year, the Krays helped a man named Frank Mitchell escape from Dartmoor Prison. Frank was a friend of Ronnie’s, as they’d spent time together in Wandsworth Prison. The idea was that the escape attempt would bring media attention to Mitchell’s case, and he’d be reviewed for parole. (And the parole board would probably find if you’re trying to escape prison maybe you need to stay in a little longer, but what do I know?) However, Mitchell never returned to prison to be paroled — in fact, he disappeared altogether and was never seen again. Freddie Foreman, a friend of the Kray brothers, would later claim in his autobiography to have shot Mitchell and disposed of his body at sea as a favor for the twins but there’s no actual evidence supporting that because nothing has ever been found.

Meanwhile, the Kray brothers continued to literally get away with murder. They socialized with A-list celebrities, their legitimate business raked in cash, and the politicians in power did everything they could to prevent any investigations even while bodies were piling up (or disappearing). In 1967, Reggie’s wife committed suicide — leaving both the mental health of both the twins in a seriously questionable state. They took out a contract to kill their financial advisor Leslie Payne, giving the contract to a minor member of the Firm, Jack “the Hat” McVitie. It was a £1000 job, and they paid £500 upfront — but McVitie failed to complete it. Ronnie convinced Reggie they had only one option: to kill McVitie as an example.

After Reggie stabbed McVitie to death, Tony and Chris Lambrianou and Ronnie Bender were called in to help dispose of the body and get rid of any evidence. McVitie was a large man and his body could not fit in the trunk of a car, so they covered him and loaded him into the backseat. The car ran out of gas in front of St. Mary’s Church, so the trio set the scene up to frame another gang for the murder and left the corpse in the car at the church. The Kray brothers were furious, and called in Foreman to finish disposing of the body — which Foreman ultimately dumped in the English Channel.

However, murdering one of their own was not a good look for the twins. Members of their gang got uneasy — wondering if what happened to McVitie could happen to them as well. At about that time, Leonard “Nipper” Read of Scotland Yard was promoted to the Murder Squad — and he’d been trying to investigate the Krays since 1964. By the end of 1967, Read had gathered enough evidence to arrest both of the Kray twins — but not enough to make the charges stick. Finally, in May of 1968, Scotland Yard arrested the Kray brothers and fifteen members of their gang. They went through elaborate lengths to prevent any of the arrested members of the Firm from speaking to each other, and offered all of them deals to testify against each other — but the Krays could. They schemed to have “Scotch Jack” Dickson confess to murdering Cornell, their cousin Ronnie Hart to confess to murdering McVitie, and Albert Donaghue to confess to murdering Mitchell. Donaghue, however, flatly refused and almost immediately turned on the twins, confessing everything he knew. Next “Scotch Jack” rolled on the twins — and with his testimony, they found the bartender who had been working in the pub where George Cornell was killed. She gave her statement as well.

The evidence became overwhelming, and the only defense was essentially to try to discredit the witnesses because they were mostly all also criminals. What followed was the longest murder hearing in British history, but it was ultimately determined that the twins were going to go to jail for life and would not be eligible for parole for thirty years. Their brother Charlie was also jailed for ten years for his help in their criminal activities.

At the time of their sentencing, Ronnie was engaged to a woman named Monica — whom he claimed was the only woman he ever loved. In the first seven months of his imprisonment, Ronnie and Monica sent 59 very affectionate letters to each other — even though she married someone else during that time. Ronnie was finally diagnosed with paranoid schizophrenia, and was sent to Broadmoor Hospital in 1979.

The twins were allowed out of prison — under heavy guard — to attend their mother’s funeral in 1982. There was basically a huge media circus about it because of their presence (and also because Diana Dors was there) so they decided to spare their family that kind of attention, and did not attend their father’s funeral in 1983.

In 1985, the staff at Broadmoor Hospital discovered evidence that Ronnie, Reggie, and Charlie were operating a business called “Krayleigh Enterprises” which offered bodyguards and “protection services” to celebrities. Frank Sinatra hired 18 bodyguards from the company when he visited the Wimbledon Championship in that year. The police investigated the business, and found no legal reason to shut it down — so, apparently, it was actually legitimately bodyguards and apparently Frank Sinatra actually legitimately needed 18 of them to watch tennis.

Also in 1985, Ronnie married a woman named Elaine Mildener who he met at Broadmoor Hospital. They divorced in 1989, after which he married a woman named Kate Howard. They divorced in 1994.

In several early interviews while imprisoned, Ronnie identified himself as a gay man, but by 1989 he was identifying himself as a bisexual man — but he certainly never denied that he was attracted to men. In fact, in one interview in the 1970’s, he said: “[Gordon of Khartoun] was like me, homosexual, and he met his death like a man. When it’s time for me to go, I hope I do the same.” In actuality, Gordon of Khartoun was not a homosexual and Ronnie met his death on March 17, 1995 from a heart attack while still being held at Broadmoor Hospital. Reggie was allowed out of prison (in handcuffs) to attend Ronnie’s funeral. (Reggie lived until 2000, when he died of cancer. He was released from prison weeks before his death on compassionate grounds.)

The Krays’ celebrity status while being horrible, awful, violent criminals has certainly left a lasting impact on our culture. There have been multiple movies, several books, and a couple of plays about them, and depictions of them appear in eight television series. But their real influence went way further than that. If you were reading this whole thinking “wow, they sound just like gangsters from the movies!” that’s because the archetype of gangster that appears in movies was essentially revamped to be more like them after their arrest — their clothes, their crimes, etc. I just kind of wish Hollywood had been a bit more fascinated with their sex scandals too.

James Barry

Like so many historical figures, James Barry‘s gender identity is kind of a mystery because the language and understanding we have of gender today has really evolved immensely since the 19th century. Nevertheless, I feel pretty confident that James Barry was transgender and not just trying to escape the confines that came with being a woman in Regency era Britain. I’ll justify that as we go through this.

He was the second child born to Jeremiah and Mary-Ann Bulkley in Ireland, though there is very little information about his early life. He was named Margaret Anne Bulkley and lived as a girl until at least age 19. What little information can be found and verified seems to indicate he was born in 1789 — for instance, a letter dated January 14, 1805 states that the young “Miss Bulkley” was fifteen years old at the time. The date of birth is a bit confusing, because there are also sources that indicate he may have been born in 1792, 1795, or 1799. These are probably due to Barry lying about his age through his military career.

There is also some indication that Barry was assaulted as a child, resulting in a pregnancy. The child this produced is theorized to be the youngest Bulkley child, Juliana, who was raised as Barry’s sister.

The Bulkley family had serious financial difficulties — and ultimately they concocted a scheme to produce a better income. “Margaret Anne” adopted the name James Barry and posed as the nephew of the Irish artist James Barry (who was Mary-Ann Bulkley’s brother). Along with his mother (his “aunt” in letters), Barry boarded a ship bound for the University of Edinburgh in 1809. It is from the envelope of one letter from this trip that researchers were able to trace Barry back to his early childhood — the back of the envelope discreetly bore the words “Miss Bulkley, 14 December.” After this point, Barry never permitted anyone to see him change clothes and lived as a man both publicly and privately.

Barry began studying medicine at the University of Edinburgh. Due to his effeminate facial features, many students believed Barry to be a pre-pubescent boy (like, some kind of prodigy, I guess?) and the university even tried to stop him from taking the final exams because they believed he was too young. The Earl of Buchan intervened, and Barry graduated in 1812 and almost immediately enrolled in courses at the United Hospitals of Guy’s and St. Thomas’. On July 2, 1813, Barry passed the examination of the Royal College of Surgeons.

220px-james_barry_28surgeon2905 — Not the most flattering portrait that’s ever been painted, is it?

On July 6, 1813 Barry was commissioned as a hospital assistant in the British army. For anyone keeping track, that’s a four day turn around on graduating school and landing a job. Barry was initially stationed at Chelsea, and then sent to Plymouth to serve at the Royal Military Hospital there. He was promoted to Assistant Surgeon to the Forces (which apparently is the medical equivalent of a lieutenant) on December 7 of 1815.

In 1816, Barry was sent to Cape Town, South Africa. Barry’s previous benefactor, the Earl of Buchan, had sent a letter of introduction to the governor Lieutenant General Charles Henry Somerset. Barry quickly impressed the governor’s family by treating his ailing daughter. Barry was essentially welcomed as a member of the family, and in 1822 Somerset promoted Barry to Colonial Medical Inspector — which was a pretty massive jump in station and in responsibility. Barry spent the next decade significantly improving conditions — especially for slaves, prisoners, prostitutes and the mentally ill. Barry even made a priority out of improving the conditions in hospitals and leper colonies. Barry is notable for being one of the handful of medical professionals at the time who understood that humanitarian conditions — particularly hygiene, diet, and fresh air — were vital to sustain a healthy population and prevent the spread of disease.

Although he used excellent bedside manner with patients, Barry was otherwise outspoken, impatient, brash, and often tactless — particularly when it came to criticizing other people when it came to medical concerns and policies. Not surprisingly, a lot of people did not like Barry because of this but his close friendship with the governor shielded him from consequences. That’s probably a large factor in one major event that took place in 1824: Lieutenant General Charles Henry Somerset was accused of “buggering” Barry. An investigation and a trial followed.

Now, buggering — which, of course, was the act of homosexual intercourse — was still very illegal in the British Empire and could still carry the death penalty. Nevertheless, nobody even seems to have considered that Barry was biologically female and Barry certainly didn’t offer up this information. This is one reason that I’m convinced that Barry identified as a man — Barry never came forward to save Somerset. Somerset also never revealed anything, even though it’s considered probable that he knew.

Though the case failed to prove any buggering, it proved humiliating for both Somerset and Barry. Barry managed to redeem himself in June of the same year — by performing a Cesarean section (without anesthesia) where both the mother and child lived. This was one of the first times this ever done and was the first time this had been accomplished anywhere in the British Empire or, as far as we know, in Africa. This feat easily secured Barry’s position as the best doctor in the colony.

On November 22, 1827 Barry was promoted to Surgeon of the Forces. The following year, he was assigned a new posting in Mauritius. After only a year there, Barry took a leave because Lord Somerset had fallen in. Barry personally cared for Somerset until his death in 1831, at which point Barry was sent to Jamaica and then, in 1836, to Saint Helena.

Barry’s abrasive personality had not mellowed out over the years, and while stationed at Saint Helena he came into some sort of, let’s say, “gentleman’s disagreement” with another officer that resulted in Barry facing a court martial that ultimately found him not guilty.

In 1840, Barry was promoted to Principal Medical Officer and assigned to the Leeward and Windward Islands of the West Indies. His assignment was to improve the conditions of the soldiers stationed there. This posting was apparently uneventful until Barry contracted yellow fever in 1845 and returned to England on sick leave. After being cleared for duty in 1846, Barry was stationed in Malta where he quickly ruffled feathers by — apparently — sitting in a seat in church that was reserved for clergy. This led to a formal reprimand, but Barry was less concerned with hurt feelings and more concerned with the looming threat of cholera. The disease ultimate did breakout, despite Barry’s efforts, and he was called on to treat it.

Although the cholera epidemic lasted until 1860, Barry’s superiors sent him to Corfu in 1851. On May 16, they promoted him to the rank of Deputy Inspector-General of Hospitals. Barry requested to be posted in Crimea, but the request was denied. In turn, Barry requested a leave and traveled to Crimea anyways. While there, Barry had a run-in with Florence Nightingale. The only descriptions I can find of the event come from Nightingale, but it sounds like Barry, on horseback, confronted her about something while she was (I’m guessing) crossing camp either to or from showers because she was basically naked. Whatever transpired, it left Nightingale with a deep dislike of Barry, whom she later described as “the most hardened creature [she] had ever met.”

james_barry_28surgeon2901 — James Barry and John Joseph Danson

On September 25, 1857 Barry received a promotion to Inspector General of Hospitals and was posted to Canada. He remained in this post, improving healthcare particularly for the poor, until he was forcibly retired from military service because of age and illness on July 19, 1859. He returned to London, where he lived quietly with only his servant John Joseph Danson (who had been with Barry since his first posting in South Africa) and a poodle named Psyche. Barry died from dysentery on July 25, 1865. Shortly thereafter, Danson disappeared — but is believed to have gone to Jamaica.

Despite having left strict instructions that his body not be examined in any capacity after his death, the truth of Barry’s biological sex was discovered. The physician who had issued the death certificate, Major D. R. McKinnon, had written on the certificate that Barry was a male. Afterwards, a woman — who is believed to have been laying out Barry’s body for burial — discovered Barry was biologically female and showed signs of having given birth at a young age. She attempted to use the secret to blackmail McKinnon. However, Barry had no known surviving family and McKinnon was not especially concerned (stating that he had figured Barry was a “hermaphrodite” but that it was “none of [his] business”), so he shrugged her off. The woman leaked this information to the press. A number of people responded by claiming to have known it all along, and Florence Nightingale responded by writing a scathing letter about how much she didn’t care what he was, she still really didn’t like him.

The British Army, in an effort to save face as women were allowed to be neither officers nor doctors and Barry had been both, sealed all records about Barry for the next hundred years. Isobel Rae, a history, gained access to the records in the 1950’s and ultimately pieced together Barry’s history from before he transitioned.

There’s a lot of discussion regarding whether or not Barry was truly transgender. Some would argue that because he transitioned with the help of his family in order to financially aid his family means it was all an elaborate ruse. Obviously, I’m firmly in the other camp that he was — living as a man even in private, not even breaking from his gender expression to prove a friend innocent of buggery, and trying to maintain that gender identity even in death despite not having any surviving family — to me, that all indicates someone who vehemently identified as a man.