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  1. Swapping Sex: A Timeline of Transgender Trailblazers

    By Ellis Cashmore

    People have been swapping sexes for centuries. In the ancient world as today, some humans rejected their assignment at birth and opted to pursue alternatives. Notable individuals have disguised, masqueraded and misleadingly represented themselves in order to live their preferred lives. In the early 20th century, when experimental surgical procedures became available, some brave souls elected to undergo what we now call a “sex change.” This timeline identifies some of the prominent pioneers of transition and their modern counterparts.

  2. c. 203–222: Elagabalus

    A Roman emperor who reigns from 218 to 222, Elagabalus is married a prodigious five times, four times to women. But in a world where there’s no binary and sex is more a continuum than a divide, the emperor’s preference for flamboyant clothes and fifth marriage to a male slave may not seem extraordinary. The ancient Romans’ understanding of sexual identity is completely different to ours. Considered male until recently, Elagabalus’ sexual status remains uncertain, but they are certainly a genderqueer   icon. They are assassinated in 222, aged 18.

  3. 1412–1431: St. Joan of Arc

    A French peasant who leads France to a historic victory over England at Orléans during the Hundred Years’ War, she becomes a national heroine and is canonized in 1920. She’s hailed as a trans pioneer for wearing her hair short and dressing in hose, doublet and armor, not the orthodox kirtle (dress), gown and hennin (headdress). She claims to have communications with saints. Captured by the English, she’s accused of heresy and burned at the stake. Some scholars believe her subversive defiance of conventional femininity contributes to her death.

  4. c. 1592–1635: Catalina de Erauso

    Born in San Sebastián, Spain, she is placed in a convent but flees at about age 15, disguised in men’s clothing. She lives with many male aliases and serves in the military at a time when women can’t. The nickname “Lieutenant Nun” is used widely for her, suggesting her biological sex is known. But de Erauso’s military service is exemplary. In 1625, she requests and gains the approval of Pope Urban VII to continue living as a man. She later dies, aged 43; the cause of death is unknown.

  5. 1789–1865: James Barry

    Born Margaret Bulkley in Cork, Ireland, she lives when women cannot study medicine. She invents the name James Barry and disguises herself as a man lifelong. Her case reveals the complexity of the relationship between gender identity and sexual orientation: Is she queer, or a functional cross-dresser? Barry’s only known relationship is a close friendship with Lord Charles Somerset, Governor of the Cape Colony in South Africa. Here she serves in the British military, excelling in a field that bars women. She dies of dysentery, aged 75–76.

  6. 1882–1931: Lili Elbe

    Arguably the best-known transgender person of the period thanks largely to the 2015 feature film, The Danish Girl, Elbe is born Einar Wegener. He spends almost all of his life as a man, marrying a woman in 1905 and moving from Denmark to Paris, France where he leads something of a double life. He is a painter and illustrator. In 1930, he undergoes the first of five experimental sex reassignment surgeries conducted by gynecologist Kurt Warnekros. Elbe dies of complications after the final procedure, aged 48.

  7. 1892–1966: Dora Richter

    Born a male in Bohemia, Czech Republic, Richter is the first known person to have gender reconstructive surgery. She dresses and lives as a woman. In 1922, she elects for an orchidectomy, the surgical removal of testicles, followed by other procedures pioneered by surgeon Magnus Hirschfeld. Around this time, biological research yields an understanding of the role of hormones in sex, metabolism and crucial bodily functions: The sexual binary is established in science. Richter dies in 1966, aged 76; her cause of death is unknown.

  8. 1914–1989: Billy Tipton

    A US jazz musician, Tipton is assigned female at birth and assumes a male identity for his life pursuits and artistic aspirations. He marries, adopts three children and spends years as a family man. He plays piano and saxophone with Duke Ellington and Frank Sinatra. After Tipton dies of a hemorrhaging ulcer in 1989, aged 74, his true sex is exposed by the media who paint his authentic existence as one of deceit. Tipton’s widow and eldest son insist they didn’t know Tipton’s secret.

  9. 1918–2011: Roberta Cowell

    Born in London, England as Bob Cowell, he is a race car driver, World War II pilot and father. In 1948, he has his testicles illegally removed and, in 1951, undergoes a vaginoplasty to create a vagina. She returns to racing, this time as Roberta Cowell. In the 1950s, racing is not commercialized; Cowell struggles financially. In 1972, she gives an extraordinary interview to Britain’s Sunday Times in which she criticizes trans people and warns others against following in her footsteps. She lives the end of her life reclusively.

  10. 1926–1989: Christine Jorgensen

    As a man named George Jorgensen, the New Yorker serves in the US Army. After World War II, he travels to Denmark for surgeries and hormone treatments. This case is sensational in the early 1950s. The New York Daily News hears of it and on December 1, 1952 runs a front page story with the headline, “EX-GI BECOMES BLONDE BEAUTY.” Jorgensen capitalizes on her fame/notoriety with a nightclub act and becomes the most celebrated trans person of her time. She dies of cancer, aged 62.

  11. 1934: Renée Richards

    In the 1950s–1960s, the US’s Richard Raskind plays top class tennis as a man, competing in the US Open five times. In 1976, two years after having sex reassignment surgery, Renée Richards tries entering again but faces opposition. She challenges and the New York State Supreme Court grants wins her a right to play, making her a reluctant trans emblem. “I like the difference between men and women,” Richards tells British newspaper The Telegraph, affirming her commitment to the traditional binary. “I like the concept of male and female.”

  12. 1948: Caitlyn Jenner

    An Olympic gold medalist in 1976, men’s decathlon champion Bruce Jenner marries celebrity Kris Kardashian in 1991. He discovers a new fame on the 2007 reality show, Keeping Up with the Kardashians. After divorcing Kardashian in 2014, Jenner makes a staggering announcement in 2015: She identifies as a woman and wishes to be known as Caitlyn. She appears on the cover of Vanity Fair with the headline, “CALL ME CAITLYN.” She takes medications to suppress male hormones and undergoes various surgical procedures, including breast augmentation.

  13. 1951–2002: Sylvia Rivera

    Born in New York, Ray Rivera is abandoned by his father shortly after birth and orphaned when his mother commits suicide. Aged 11, he runs away from home and grandmother, and lives on the streets. A group of drag queens become surrogates and Sylvia emerges. She is involved in the Stonewall Riots of 1969 and becomes one of the most effective LGBTQ+ activists of her time. She establishes the Street Transvestite Action Revolutionaries (STAR) organization with fellow drag queen, Marsha P. Johnson. Rivera dies of cancer in 2002.

  14. 1965: Andreas Krieger

    A product of East Germany’s State Plan 14.25, a state-sponsored performance-enhancing doping regime, Heidi Krieger wins a gold medal as a woman in the 1986 European Athletics Championships. As she matures, Krieger experiences unwelcome physical and emotional changes as a result of the drugs. In 1997, he becomes Andreas Krieger after surgery. In 2002, he marries female swimmer Ute Krause. In 2000, the International Olympic Commission ends genetic gender testing for female athletes, instead focusing on visual assessments and medical histories.

  15. 1973: Valentina Petrillo

    Neapolitan Fabrizio Petrillo is by far the most publicized and controversial transgender athlete to compete in the Paralympics. Her every appearance in sports events provokes dispute, especially the 2024 Paralympics, where she competes for Italy in the T12 women’s 400 meters. Petrillo competes on the track as a man, winning 11 national competitions in the male T12 category between 2015 and 2018. After transitioning and undergoing a course of testosterone suppressants, Valentina Petrillo is eligible for women’s events in 2020, aged 47.

  16. Credits
    Written by Ellis Cashmore
    Edited by Lee Thompson-Kolar

    Produced by Lokendra Singh
    Images courtesy of Wikimedia Commons
    [Ellis Cashmore’s latest book is The Destruction and Creation of Michael Jackson.]