16 Remarkable Historical Figures who were Transgender

15. Moll Cutpurse: The Cross-Dressing Thief, Madame, and Highwaywoman of seventeenth-century London.

Mary Frith or Moll Cutpurse was a career criminal who picked pockets, fenced stolen goods and pimped out both men and women. If we are to believe her legend, she was also an ardent royalist who took to the road in her fifties during the English Civil war, robbing “Roundheads, or rebels, that fomented the Civil War against King Charles I.” Moll, however, was also notable for living her life very much on her terms as a cross-dresser. According to the Newgate Calendar, Moll had possessed a “boisterous and masculine spirit, ” since childhood. She was a “tomrig” who “delighted only in boys play, ” and avoided all feminine pursuits.

As an adult, Moll became notorious in the London underworld for drinking in taverns, smoking a pipe, carrying a sword- and for dressing and behaving like a man. The Newgate calendar records how Moll took to wearing britches and hose “from her first entrance into a competency of age, and to her dying day.” This habit led to a court summons which led to Moll being sentenced to do penance on a white sheet outside St Pauls to atone for her ‘sins’. It did not, however, cause Moll to change her ways. Because of her dress and behavior, many of Moll’s neighbors believed her to be hermaphrodite. Her death disproved this. However, Moll Cutpurse’s habits and way of life suggest that in her mind, she was no conventional woman.

14. Chevalier D’Eon: The French spy and soldier who spent the last thirty-three years of his life dressed as a woman and inspired the term “Eonism.”

In 1756, Charles-Genevieve Louis August Timothee D’Eon de Beaumont became a spy when he joined “The King’s Secret,” a clandestine organization answerable only to King Louis XV. D’Eon androgynous appearance made him the perfect candidate for a very particular assignment, and he spent the next few years disguised as a maid of honor in the court of Empress Elizabeth of Russia. In 1760, D’Eon returned to France, ditched his female clothing, and joined the dragoons to fight in the Seven Years War. He distinguished himself, was awarded the title “Chevalier” and, when the hostilities were over, became the French ambassador in London.

However, Louis XV exiled D’Eon after he threatened to expose The King’s Secret. He remained in England until after the death of the King. Then he returned to France- dressed as a woman. D’Eon’s contemporary, Madame Campan claimed this disguise was a condition of D’Eon returning home. However, D’Eon lived the rest of his life as a woman. He even petitioned to be recognized as female, claiming his parents had only registered him as a boy for inheritance purposes. When he died in Southampton in May 1810, doctors found he had “male organs in every respect perfectly formed” but some feminine attributes such as ‘rounded limbs‘ and breasts that were “remarkably full.” D’Eon’s sexual ambiguity coined the phrase “Eonism” which was used for a time to describe those with transgender characteristics.

13. We’wha: The “Two-spirited” Zuni tribesman who made it big in America as an Indian Princess.

In 1849, the Zuni tribe of New Mexico and American settlers become allies when they had banded together against their common foes the Navajos and Apaches. In 1877, American missionaries finally settled amongst the Zuni and began to experience the uniqueness of their culture firsthand. For amongst their domestic help was We’wha, a well-respected Zuni tribesman, who confused them by dressing like a woman and performing female tasks. This contradiction occurred because We’Wha was a lhamana or “two-spirited”; a male at birth but gifted with blended male and female characteristics.

The Zuni accepted Lhamana as a third gender. At puberty, Lhamana underwent Zuni manhood ceremonies, but they also dressed as women and were taught female tasks. This blending of roles proved equally confusing to American anthropologist Matilda Cox Stevenson who befriended We’wha in 1879. She described We’wha as “the strongest character and the most intelligent of the Zuni tribe” and marveled how his word was Law amongst men and women. However, she claimed she did not know her friend was a man until after his death. Cox Stevenson introduced We’Wha to Washington society, which accepted him as a Native American Princess. However, the lhamana soon returned home- to lead a revolt by the Zuni against their American allies.

12. Albert Cashier: The Heroic and Tragic Union Solider who fought 40 battles in the American Civil war, but was born a woman

In 1859, sixteen-year-old Irish girl Jennie Irene Hodgers left her home in the Irish fishing village of Clogherhead. Jennie’s destination was New York. However, by the time she arrived in America, Jennie had adopted a new name- and a different gender. For Jennie stepped off the boat in New York as Albert Cashier– a role she claimed in later life she adopted to find work. In 1862, Albert took this male lifestyle to a whole new level when he enlisted in the 95^th Illinois Infantry of Abraham Lincoln’s Union army to fight in the American Civil War.

Albert fought in approximately 40 battles. He was known as a brave soldier, who would taunt the enemy into action and who escaped a Confederate soldier who captured him, by knocking the man out and running back to camp. After the war, Cashier continued to live and work as a man. However, an accident revealed his female identity physique. As a result, Cashier had to fight to retain his army pension. He won his case but a decline in his mental health to force him into a mental asylum where he died in 1915. The hospital forced Cashier to live as a woman, and the distressed former soldier tried to fashion his skirts into pants using safety pins. It was a cruel end to a courageous life.

11. Harry Allen: The Tough Living Transgender Man of the American West

Nell Pickerell began to dress as a man at a young age. With a violent, alcoholic father, life was hard in the family, and so young Nell needed to find work. Boys always obtained the most lucrative jobs – so Nell began to dress in male clothing, using the name Harry Allen or occasionally Harry Livingston to help her get work. In his teens, Harry graduated from working as a farmhand to working on an ocean liner sailing between San Francisco and Sydney. The work was hard, but Harry enjoyed it. Back in America, Harry settled in various Midwest towns where he continued to live as a man.

Harry lived a tough life, making a living as a petty criminal and earning a reputation as a rabble-rouser. He got into drunken fights, once throwing a spittoon at a man in a saloon. He also became notorious for ‘seducing’ pretty girls. Harry served jail time for many of these crimes and misdemeanors, and when the media found out the “most handsome boy” was, in fact, a woman, they had a field day. The reports continually emphasized Harry’s ‘female’ identity- even though Harry himself regarded himself as male despite his designated female gender. Eventually, the pain of being so shamed and misunderstood took its toll. Harry began to depend increasingly on drugs and alcohol and in 1922 died aged 40.

10. Karl Baer: The German woman’s rights activist who became the first person to undergo sex-change surgery.

When Martha Baer was born on May 20, 1885, the midwife told the new baby’s parents that they had a daughter. However, afterward, she privately confided to Martha’s father that his daughter’s body had “such strange characteristics that she had no way of determining the gender.” Childhood proved uncomfortable for young Marthe who stated later in life she was “born as a boy and raised as a girl. At puberty, ‘she’ did not develop a woman’s body. Finally, in 1904, Baer abandoned any pretense at femininity and began to live as a man, while at the same time campaigning for women’s rights.

However, not all of Baer’s fellow feminists were at ease with ‘her’ masculine appearance. Then in 1906, fate took a hand. Baer went to a hospital after being knocked over by a tram, and ‘her’ unusual anatomy was noted. Dr. Magnus Hirschfeld, a sexologist subsequently diagnosed Baer as “a man who was mistakenly identified as a woman.” Hirschfeld arranged corrective surgery, and later that year, Baer became the first person to have sex-change surgery. Marthe finally became Karl, and on January 8, 1907, a court ratified Karl Baer’s male identity. Karl Baer later recorded his experiences in a semi-fictional memoir” “Man’s Years as a Young Girl” He married twice and ended his life as an accountant living in Israel.

9. Alan L Hart: The First Female to Male Gender Transition in American History

Alan Hart was born Lucille Hart on October 4, 1890. As a young child, Lucille found she much preferred dressing as a boy. On her grandparent’s farm, this was fine. However, the school forced Hart to dress and behave as a female. To counter this, Hart began to write for local publications using a male pseudonym and shying away from feminine topics. However, ‘she’ could not escape her defined sex and in 1917 was awarded a medical degree under his female name- even though sympathetic staff suffixed the records with the name Hart’s chosen name, Robert.

The new Dr. Hart began to explore ways to minimize his femininity. So he approached Dr. Joshua Gilbert of the University of Oregon and asked him if he could stop menstruation and remove any possibility of pregnancy. Gilbert examined Hart and declared him primarily male. As Gilbert deemed living as a woman was detrimental to Hart’s well-being, he then approved the removal of Hart’s womb. This operation was not only the first-ever hysterectomy of a healthy uterus; it also allowed Hart to change his sexual identity. Hart was able to deepen his voice and grow facial hair after the development of synthetic testosterone after the Second World War allowed. He married twice, and helped pioneer the use of X-ray in the treatment of TB,- as well as forging a successful second career writing novels.

8. Dora Richter: The World’s First Male to Female Sex Change who was killed by the Nazis.

Rudolph Richter displayed a tendency from early childhood, to: “act and carry on in a feminine way.” ‘He’ expressed distaste for male clothing and at the age of six, tried to tourniquet his penis. After this, Rudolph’s family allowed him to live as a girl as much as possible. However, adult life was cruel. During the summer, Richter worked as a male waiter in various Berlin hotels. But when autumn came, he lived as a woman. This habit led to the authorities arresting and imprisoning Richter several times for cross-dressing. However, eventually, Richter encountered a liberal judge, who referred him to Magnus Hirschfeld, a Jewish-German doctor at the Institute for Sexual Research in Dresden.

Hirschfeld had already helped Kurt Baer make the transition from female to male. At the institute, he helped Richter obtain a permit to wear women’s clothes and employed him as domestic help. Richter became one of five such employees at the Institute who were treated entirely as women. In 1922, Dr. Erwin Gohrbandt medically castrated him. The castration made Richter’s body ” fuller, restricting her beard growth, making visible the first signs of breast development, and giving the pelvic fat pad… a more feminine shape.” After nine years, more surgery gifted Richter with a vagina – a world first-and finally removed her penis. However, Dora Richter’s new life was short-lived. In 1933, the Nazis attacked the Institute and killed many of the patients. Dora Richter was one of them.

7. Lili Elbe: “The Danish Girl” whose desire to live a full female life killed her.

The subject of the film, “The Danish Girl,” Lile Elbe is one of the most famous transgender figures of recent times. She was born Einar Wegener in Denmark in 1882. Einar showed no discernible signs of being transgender until his life changed forever when his wife, the illustrator Gerda Gottlieb asked him to stand in for one of the regular models she used for her illustrations in Paris fashion magazines. The effect of women’s clothing upon Einar was instantaneous. “I liked the feel of soft women’s clothing,” Einar later wrote.” I felt very much at home in them from the first moment.”

Einar began dressing as a woman regularly, accompanying Gerda about Paris, posing as her sister Lile. However, after fifteen years, Einar’s duel nature began to take its toll. He felt two people were fighting for supremacy over his body: the “steady and sensible” Einar and the “superficial, thoughtless and flighty,” Lile. After a suicide attempt, Lile won. Doctors referred Einar to the Dresden Institute where surgeons removed his penis and implanted ovaries. Lile and Gerda divorced, and Lile began a relationship with Claude Lejeune, a French art dealer with whom she hoped to have a child. In 1932, doctors implanted a womb transplant, but Lile’s body rejected it. By September Lile was dead of the resulting infection.

6. Christine Jorgensen: The First Transgender American to go public

Christina Jorgensen was not the first American to have a sex change as is often claimed, but she was the first transgender person to announce her gender reassignment publicly– and to fight to make the transgender phenomenon better understood. Born George William Jorgensen, in the Bronx in 1926 Jorgensen was a shy, frail, little boy who avoided rough games and fights. Jorgenson explained in later interviews that her childhood was happy. However, the onset of puberty led to the feeling she was a woman in a man’s body.

After hearing about pioneering work in Europe, Jorgensen began to explore making the transition from male to female. In 1950, he started taking estrogen under the supervision of Dr. Christian Hamburg and in 1951, began gender reassignment procedures in Copenhagen, Denmark. The surgery transformed Jorgenson physically and mentally. She chose a new name ‘Christina’ in honor of her doctor and in 1955 returned to America. An outgoing ‘Blond Beauty‘ now replaced the shy little boy and Christina Jorgenson fast became a celebrity; acting and entertaining as well as speaking up as an advocate for transgender people on TV and radio. She died in 1989 of bladder and lung cancer, having, as she put it given the sexual revolution “a good swift kick in the pants.”

5. Lucy Hicks Anderson: The Black American Transexual who pioneered marriage equality

Tobias Lawson was born in Kentucky in 1886. From his earliest childhood, he identified as female, insisting on girl’s clothes- and being referred to by the name ‘Lucy.’ Tobias’s desperate mother took him to see a doctor, who was surprisingly enlightened for the times and suggested that she raise her son as a girl. After school, Lucy worked as a domestic and in a hotel. Then in 1920, she married her first husband, Clarence Hicks. The couple moved to California, where Lucy saved up to open a brothel. In 1929, she divorced Hicks, remaining single until she married soldier Reuben Anderson in 1944.

Throughout this whole time, no one doubted that Lucy was biologically female (although her two husbands must have known the truth!). However, in 1945, the secret was out, and the authorities decided to prosecute her for fraud as she had married as a woman when she was physically male. Lucy, however, remained defiant. “I defy any doctor in the world to prove that I am not a woman. I have lived, dressed, acted just what I am, a woman.” She declared. The court placed her on probation for ten years. However, the US army was less sympathetic, and the following year, Lucy served time for receiving allotment cheques as Reuben Anderson’s wife.

4. Michael Dillon: British Transsexual and author of the first book on transgender identity

Michael Dillon was born Laura Maud Dillon, the second child of Robert Dillon, heir to the Baronetcy of Lismullen. Dillon never felt comfortable as a girl although he excelled at sports, winning a University sporting blue for rowing at Oxford. In 1939, Dillon took steps to alleviate some of the discomforts of living in a female body. He consulted George Foss, a Bristol doctor who used testosterone to treat extreme menstrual bleeding. Dillon asked for treatment to stop his periods altogether. So Foss referred Dillon to a psychiatrist- who duly spread the tale around the city, forcing Dillon to flee the scandal.

During the Second World War, Dillon lived as a man, working as a mechanic and air raid warden. One night, Dillon was hospitalized. However, he had the good fortune to encounter a sympathetic doctor who was also one of the world’s first plastic surgeons. The doctor performed a double mastectomy on Dillon and gave him a note so that he could become Laurence Michael Dillon. Between 1946-1949, Dillon had thirteen gender reassignment surgeries. He began to study medicine- and in 1946 wrote the first book about transgender identity: “Self: A Study in Endocrinology and Ethics.” “Where the mind cannot be made to fit the body, the body should be made to fit, approximately at any rate, to the mind, ” wrote Dillon.

3. Roberta Cowell: The Fighter pilot who became the first British Transgender woman to Undergo Gender Reassignment.

Born in 1918, Robert Marshall Cowell initially exhibited no doubts about his gender. He was an enthusiastic member of his school’s motor club and at sixteen became an apprentice aircraft engineer. In 1936, while studying for his engineering degree, Cowell also raced in several Grande Prix. However, during the Second World War, while serving as a British fighter pilot, Cowell was shot down and captured by the Germans and confined to Stalag Luft 1 prison of war camp. There, the married Cowell witnessed several of his fellow prisoners start same-sex relationships. Although he did not participate himself, Cowell found himself increasingly paranoid about being seen as feminine.

After the war, a depressed and traumatized Cowell separated from his wife and sought psychiatric help. Therapy and Michael Dillon’s groundbreaking book finally helped Cowell to come to terms with the fact that his “unconscious mind was predominantly female.” By 1950, Cowell and Dillon were friends, and in 1951, Dillon carried out Cowell’s gender reassignment surgery. In 1972, Cowell explained in an interview that this surgery was justifiable because she had a chromosomal abnormality, XX male syndrome. However, she was less than sympathetic to other transgender men seeking to change sex, claiming if they had standard XY chromosomes, reassignment surgery, would turn them into ‘freaks.’

2. Sir Ewan Forbes: The Intersex Aristocrat who successfully inherited his family title.

Sir Ewan Forbes of Craigievar, the 11th Baronet, was born Elizabeth Forbes-Sempill on September 6, 1912. At birth, Forbes’s sex was hard to determine because he was intersex. So, his parents decided to designate him as a girl as it seemed the best option. However, as Forbes grew up, it was clear this was a mistake. He insisted on wearing boy’s clothes and preferred to play with his male cousins rather than his sister. Forbes even refused to be sent away to a girl’s school, forcing his parents to educate him at home until he was old enough to attend a co-educational institute in Dresden.

In 1945, Forbes qualified as a doctor and finally began to live as a man. By 1952, he had reregistered as male, changed his name and married his housekeeper. A press release revealed his change of gender was due to “…a ghastly mistake. I was carelessly registered as a girl in the first place.” In 1965, Forbes’ elder brother died childless, leaving Forbes his heir. A male cousin challenged the inheritance, on the grounds of Forbes’ original gender. However, the subsequent court case was found in Forbes’ favor because the initial determination of his sex was faulty. Ironically, as Forbes never had any children himself, his troublesome cousin eventually inherited his title and lands on his death in 1991.

1. Renee Richards: The First Transgender Woman to Play a Professional sport.

Renee Richards is a world-renowned eye surgeon and in the 1970s was a famous international female tennis player. However, until she underwent gender reassignment surgery at the age of 41, Renee was a 6ft 2in surgeon called Richard Raskin. As Raskin, Renee had captained the Yale tennis team and won several tennis titles. However, despite marrying and fathering a son, Renee had always been conflicted about her sexual identity; a conflict she did not resolve until 1975 when her physical gender finally became female.

In 1976, Richards began to play tennis as a woman. However, her birth sex was quickly outed, and the US open promptly tried to stop her from competing as a woman by introducing a chromosome screening procedure. So Richards decided to sue. The USTA lawyer George Gowan attempted to argue that allowing Richards to play would be opening the floodgates to “worldwide experiments, especially in the Iron-Curtain countries, to produce athletic stars by means undreamed of a few years ago.” However, the judge observed there were relatively few athletes in Richard’s position – and ruled in her favor, allowing Richards to compete in the 1977 US Open. The judgment made Richards a trailblazer against transgender discrimination.

Where Do We Get this stuff? Here are our sources:

History Collection – 11 Remarkable Transgender People from History

National Geographic Channel – The Short Reign of Elagabalus, Rome’s Hard-Partying Emperor

Historic UK – Moll Frith

“Why tennis’s Renée Richards, the first transgender woman to play Professional sport, matters today”, Simon Briggs, The Telegraph, March 30, 2018.

The Newgate Calendar: Comprising Interesting Memoirs of the Most Notorious Characters Who Have Been Convicted of Outrages on the Laws of England Since the Commencement of the Eighteenth Century; with Occasional Anecdotes and Observations, Speeches, Confessions, and Last Exclamations of Sufferers, Volume2, Andrew Knapp and William Baldwin, J Robins and Company, 1825.

“When Jennie came marching home – An Irishwoman’s Diary on Albert Cashier and the US civil war”, Nora-Ide McAuliffe, The Irish Times, April 10, 2018

Crosscut – Meet Harry Allen, Transgender At-Risk Youth of Yesteryear

The Guardian – Gerda Wegener: ‘The Lady Gaga of the 1920s’

The Irish Times – Ireland’s Remarkable Trans Pioneer: ‘People Thought I Was A Woman, But I Was Just Me’

Scientific America – The Surprisingly Old Science of Living as Transgender

“How Catherine Madden Fell Victim to Strong Drink; Why Nell Pickerell Will Not Wear Women’s Clothing”, The Spokesman-Review, October 22, 1911

“Nell Pickerell Denies Her Sex; Woman Who Dresses in Male Attire Starts Story She is a “Real Man”; Rumor Causes Sensation; Sheriff Stone Brands Statement an Untrue Fabrication Result of Liquor,” The Spokesman-Review, November 22, 1911.

New York Times – Overlooked No More: Roberta Cowell, Trans Trailblazer, Pilot and Auto Racer

“Meet Nell Pickerell, transgender at-risk youth of yesteryear; She lived a century ago – as a man. But Nell’s story rings true today and parallels the experience of many Northwest street kids”, Knute Berger, Crosscut.com, June 30, 2014

Anderson, Lucy Hicks [Tobias Lawson] (1886-1954), Kevin Leonard, Black Past.org

BBC Sports – LGBT+ History Month: Renee Richards’ Journey from Tennis Outcast To Trans Pioneer