1868-1935: Medical Magnus Hirschfeld: Was a German physician who was a pioneer in research and treatment of transgender individuals as well as an advocate for the social rights of sexual and gender minorities. He was also gay and Jewish, neither of which endeared him to the Nazis when they came to power.
1885-1986 Medical Harry Benjamin was a German physician who was the leading researcher and service provider of medical services for transgender individuals in the United States, immigrating there in 1913. He began practicing in New York focussing on endocrinology seeing transgender patients as early as the late 1920s but primarily focussing on cisgender patients prior to the late 1940s. He later operated a bicoastal practice in New York and San Francisco.
1886-1954 Legal Lucy Hicks Anderson was a Black trans woman who, having preferred dresses as a child, was recommended to be raised as a girl by her family doctor. She married and divorced her first husband, Clarence Hicks between 1920-1929. While with Hicks, they moved to Oxnard, CA where she hosted popular parties and later operated a brothel. Her second marriage, to Reuben Anderson in 1944 was voided by the courts in 1945 after an investigation of a VD outbreak was traced to her establishment, and she was given jail time for perjury and fraud, exiled from Oxnard, and legally constrained from wearing women’s clothing until her death in Los Angeles in 1954. At her trial she proclaimed “I defy any doctor in the world to prove that I am not a woman. I have lived, dressed, and acted just what I am—a woman.” Her story was featured in the 2020 HBO Max documentary mini-series Equal.
1906 - Medical Karl M. Baer, assigned female at birth but probably intersex, having male features, had surgeries sometimes described as the first gender confirmation surgeries, involving removal of ovaries & uterus and some degree of masculinizing gender confirmation surgery.
1907 Culture January: The word “transsexual” appeared in the New York published Medical Times, not in its modern sense but more as a descriptor of the different social behaviors that some men perform towards women but not to men, particularly offensive ones like cat-calling.
1907: Culture Harry Benjamin met Magnus Hirschfeld. They toured gay bars and drag shows
1907-1960 Culture Gladys Bentley a singer, was a lesbian who wore men’s clothes on and off the stage.
1908 Culture In the Medical Times, the word “trans-sexual love” is used to indicate love between a man and a woman.
1909 - 1933: Legal With the cooperation between Hirschfeld and the Berlin Police, Transvestite passes are issued to trans women and trans men allowing them to proceed unharassed by the law while publicly attired according to their gender.
1910: Medical Hirschfeld published his book Die Transvestiten. Some suggest that he coined the word transvestite there, but it appears to predate him by as much as 250 years. This word serves as an umbrella term encompassing who we would today call crossdressers, as well as transgender people including those whom we have called transsexuals. In the United States, such folks along with gays, lesbians, and bisexuals were bundled together as “sexual inverts”.
1910-1985: Culture Pauli Murray - a person today who would likely have been considered a trans man, and whose pronoun use varied
1913: Medical Havelock Ellis proposed the term sexo-aesthetic inversion as a better descriptor to what Hirschfeld called transvestism and what would now be considered being transgender. “Sexual inversion” had been a term describing both trans behavior and homosexuality from the 1880s
1913: Culture Amelio Robles Avila began presenting as male full time when he became a soldier in the Mexican Revolution. In the 1930s he married a woman and they adopted a daughter. He was known to threaten to shoot anyone who misgendered him.
1914:Medical Ernst Burchard apparently coins the term “cisvestitismus” or “cisvestism” in an academic sexology text called "Lexikon des gesamten Sexuallebens" or "Encyclopedia of the Whole Sex-life", in opposition to “transvestite” and meaning one who conforms to social norms of gendered presentation and expression for their birth designated sex (or does so but in clothing of a different age, profession or ethnicity for sexual relief).
1915 Culture Ben Rosenstein aka Ben Cohen aka Ida Weinstein of Chicago, died at the young age of 26. His wife told that they had determined they could live well together and earn more money with one of them living as a man, which Ben did for six years. His wife also declared that she had wanted to take the male role but demurred to Ben’s opposition on that. It’s unclear if all of this was due to Ben being a trans man, or the couple being lesbian, or if they were platonic friends who wanted a higher household income. In addition, his obituary referred to him as having lived in “trans-sexed attire” where trans-sexed’s closest contemporary meaning appears to be “crossdressed.”
1918/9: Culture Jennie June, a trans woman, published her Autobiography of an Androgene , under the pen name of Ralph Werther, detailing her life in New York in the 1890s-1910s, including her castration and her sex work. In 1922, she published the sequel, The Female-Impersonators.
1919-1933: Medical Institut fur Sexualwissenschaft - This was the premier location for research and medical practice related to sex and gender. Under the direction of Magnus Hirschfeld, the earliest medical transitions were supervised here.
1920 Medical : Havelock Ellis having previously proposed “sexo-aesthetic inversion”, then proposed the term eonism after the Chevalier d’Eon to describe people who were trans feminine. More particularly “On the psychic side, as I view it, the Eonist is embodying, in an extreme degree, the aesthetic attitude of imitation of, and identification with, the admired object. It is normal for a man to identify himself with the woman he loves. The Eonist carries that identification too far, stimulated by a sensitive and feminine element in himself which is associated with a rather defective virile sexuality on what may be a neurotic basis.”
1920 Medical :Alexis Carrel performed the first xenotransplants of ape testicular material into human cisgender men for androgenic therapy. He performed similar xenotransplants of ovarian material into cisgender women later.
1922 & 1931 Medical Dr. Levy-Lenz & Dr. Gohrbandt performed gender confirmation surgery (orchiectomy in 1922, penectomy and vaginoplasty in 1931) on Dora Richter. More on Dora Richter. It's uncertain whether or not she was present for the Nazi raids on the Institut fur Sexualwissenschaft in 1933, but she managed to survive the war, have her name updated in Czechoslovakia on her baptismal records in 1946, and move back to Germany for the remainder of her life until 1966.
1923 Medical Hirschfeld described “seelischem Transsexualismus” “psychic or mental transsexuality”in “Die intersexuelle Konstitution from the Jahrbuch für sexuelle Zwischenstufen”
(Source some of the information on Hirschfeld and related work is here.)
1926 Culture This lengthy article on Trans Liminality in the Nazi State gives extensive detail on trans lives under the Third Reich and the Weimar Republic before it.
1927 Medical Ewan Forbes, a Scottish noble and trans boy, was given treatment of a synthetic testosterone at age 15 as a result of touring various medical facilities in Germany with his mother.
1928 Medical Progynon - Estriol (E3) and estrone (E1) extracted first from ovarian and fetal tissue, and later from the urine of pregnant women and then put into pill form, is introduced by Adolf Butenandt in Germany. This had been preceded by decades of use of less purified extractions from animal glands. It was independently isolated and developed as the pill Emmenin in Canada in 1930. In combination with anti-androgens they were used in feminizing hormone therapy possibly as early as that year for trans patients such as Otto Spengler, as prescribed by Harry Benjamin.
1928-1933 (approximately) Culture Growing throughout prohibition, New York ball culture became more popular beyond the queer scene, morphing into the “pansy craze”.
1930s Culture Participants at drag balls are sometimes referred to as being of “the third sex”
1930 Medical In Germany, the magazine “The Third Sex - The Transvestites” Das 3. Geschlecht1 — Die Transvestiten publish articles by and about trangender people (“transvestite” was more of a catch all term for trans folks then.)
1930-1931 Medical Danish artist, Lili Elbe underwent a series of procedures for gender confirmation surgery, which was completed but she died from complications from rejecting a transplanted uterus. She published her autobiography Fra mand til kvinde (Man into Woman) in 1931, the year of her death. A fictionalized account of her story is told in the movie The Danish Girl.
1931 Medical Dora Richter, Charlotte Charlaque, and Lili Elbe’s surgeries mark the beginning of the history of gender-affirming vaginoplasty
1933 May Legal Medical The Nazis closed down the Institute fur Sexualwissenschaft and destroyed Hirschfeld’s writings while he was out of the country on a speaking tour, which began in 1931. He never returned. The Hamburg police were directed to send transvestites to concentration camps. Some of the more famous photos of Nazi’s burning books are of those from Hirschfeld’s institute.. This lengthy Twitter thread details the fate of a number of trans people under the Nazis. This article further details the fate of trans people in Nazi Germany. Eli Erlick further chronicles Trans Holocaust History with colorized photographs and records of trans people killed or otherwise persecuted by the Nazis.