Michael Dillon: The Doctor Who Became The First Trans Man In Surgery And The First Western Monk At Rizong
- Daniel Holland
- 2 hours ago
- 9 min read
In the spring of 1958, a quiet ship’s doctor aboard a British merchant vessel received a telegram that would expose a secret he had kept for fifteen years. The message, from a London newspaper, bluntly asked whether he intended to claim his aristocratic title “since your change-over.” The doctor was Dr Laurence Michael Dillon, the first known transgender man to undergo a phalloplasty, a writer, Buddhist monk, and physician who had quietly transformed both his body and his life long before the world knew his name.
For Dillon, the telegram marked a collision between privacy and public curiosity. By then, he had studied Greats at Oxford, qualified in medicine at Trinity College Dublin, worked as a ship’s surgeon, written an early ethical study of gender medicine, and become a novice monk in a Tibetan monastery. His life was a series of transitions, not only between genders but between faiths, professions, and continents.
Early Years and the Sense of Self
Laurence Michael Dillon was born in 1915 in Ladbroke Gardens, Kensington, into a family bound by privilege and tragedy. His father, Robert Arthur Dillon, a former Royal Navy officer and heir to the Irish baronetcy of Lismullen, struggled with alcoholism and instability. His mother, Laura Maude McCliver, died of sepsis less than two weeks after Michael’s birth. By the time he was ten, both parents were gone, and he and his elder brother Bobby were sent to be raised by two aunts in Folkestone.
The aunts were wealthy yet austere, steeped in Edwardian social propriety and conscious of class boundaries. Summers were spent in County Meath at the family estate, burned down by Sinn Féin in 1922 but later rebuilt, where Dillon learned to fish, shoot, and love the quiet logic of the countryside. But even as a child, he felt a fundamental dissonance between how others saw him and how he saw himself.
Educated at Brampton Down Girls’ School, Dillon excelled academically and developed an early interest in theology. Local vicars encouraged his curiosity about spirituality and ethics, subjects that would shape his later life. But he also gravitated toward physical and traditionally masculine activities, asking for his hair to be cut like his brother’s and joining in boys’ games when he could. He once recalled realising, when a boy held a gate open for him as if for a lady, that the world viewed him differently than he felt inside. He even tried binding his chest with a belt, only to be warned by a classmate of the danger. The discomfort was physical, but it was also existential.
Oxford Discipline and Bristol Decisions
Encouraged by a sympathetic clergyman, Dillon entered the Society of Oxford Home Students (now St Anne’s College) in 1934, initially to study theology. Before long, he switched to Greats (classics, philosophy, and history) persuading the college to support his change in course.
At Oxford, he discovered rowing, which offered both physical freedom and a measure of equality. Dillon became president of the Oxford University Women’s Boat Club and campaigned tirelessly to make women’s rowing match the men’s in discipline and recognition. He fought for women to row upstream, to wear suitable clothing, and to race against each other rather than merely against the clock. His efforts were rewarded with sporting “blues” in 1935 and 1936, and in 1937 the Daily Mail featured his photograph with the caption, “How unlike a woman!” The irony was not lost on him.
During his time at Oxford, Dillon also began to adopt a more masculine appearance: smoking a pipe, riding a motorbike, and wearing his hair cropped short. He confided in a close friend who helped him buy men’s clothing and sneak into all-male boxing matches. Though he felt isolated, he later remembered his university days fondly, describing himself simply as “an Oxford man.” He graduated in 1938, quietly determined to live as one.
Bristol and the Beginnings of Transition
After Oxford, Dillon took a laboratory job in Bristol dissecting human brains, work that deepened his interest in the physical and psychological connections of the body. When war broke out, he briefly volunteered for the Women’s Auxiliary Air Force but withdrew after learning he would be housed exclusively with women.
It was in Bristol that Dillon learned of Dr George Foss, who was experimenting with testosterone to treat severe menstrual pain. The hormone, newly synthesised, produced masculinising effects, and Dillon saw in it a possible path to becoming the person he already knew himself to be. Foss agreed to prescribe testosterone after a psychiatric evaluation, and Dillon became, so far as records show, the first person to take the hormone specifically for gender affirmation.
But confidentiality was breached: a psychiatrist disclosed Dillon’s treatment to colleagues, and soon the gossip spread. Forced to leave the laboratory, he found work as a petrol pump attendant at College Motors in central Bristol. There, among the smell of oil and petrol, Dillon began to live more openly as male. The transition was gradual but visible. Testosterone deepened his voice and changed his physique, and within a few years, both colleagues and customers accepted him as “Michael.”
Although the work was far from ideal, and his co-workers offered little but senseless bullying, Dillon was able to form a friendship with a young man named Gilbert Barrow. Barrow worked alongside Dillon for only a short time before he was called to serve in the Navy, but Dillon remembers that time fondly:
“Then I asked him if he knew since he had never given any sign but always treated me as if I were another fellow. ‘Oh yes,’ he said, ‘They told me the first day, but I told them I would knock the block off anyone who tried to be funny about you. I also said you really were a man and that had them puzzled. They didn’t know what to believe then.’ ‘A faithful friend is a strong defense and he that hath found one hath found a treasure.’ So said Solomon in his wisdom. My debt to G. [Gilbert] for this loyalty in my darkest hour could never be repaid although I did my best in later years.” – Out of the Ordinary, pg. 93
During long nights as the garage’s firewatcher during wartime air raids, Dillon began writing Self: A Study in Ethics and Endocrinology, a philosophical treatise arguing for compassion and scientific understanding toward those seeking to change sex. He did not disclose his own situation in the text but wrote from the standpoint of reason and empathy. Published in 1946, it would become a pioneering work of transgender ethics.
His physical transition continued. Suffering from hypoglycaemia, Dillon was hospitalised in 1942 at the Bristol Royal Infirmary, where a sympathetic surgeon performed a double mastectomy. The same surgeon encouraged him to change his legal documents and told him of the renowned plastic surgeon Sir Harold Gillies, who had developed genital reconstructive techniques while treating soldiers wounded in the First World War. Dillon wrote to Gillies, and a correspondence began that would transform his life.
Trinity College and the Surgeries at Rooksdown House
In 1944, Dillon legally changed his name to Laurence Michael Dillon. With the help of an Oxford tutor who quietly altered his academic records to reflect attendance at Brasenose College (then a men’s institution) he was able to enrol in medicine at Trinity College Dublin in 1945.
During university holidays, Dillon travelled to Rooksdown House in Basingstoke, where Sir Harold Gillies and his team had developed a clinic for reconstructive surgery. There, beginning in 1946, he underwent a series of complex operations, staged phalloplasty procedures using grafts of skin from his leg and abdomen. Gillies falsified medical notes to protect Dillon’s privacy, recording the diagnosis as “severe hypospadias.”
Despite infections and painful recoveries, Dillon described his time at Rooksdown as deeply affirming. He joined in ward life, even serving as master of ceremonies at Christmas parties, and for the first time felt that his physical reality matched his inner sense of self.
At Trinity, he was again a distinguished rower, competing for the men’s team and likely becoming the first person in Oxford or Dublin history to earn sporting honours as both male and female. His aunts accepted him as their nephew, though his brother never did, forbidding him from publicly associating with the family title.
Roberta Cowell and the Ethics of Early Transition
Dillon’s Self brought him into contact with Roberta Cowell, a race-car driver and former RAF pilot seeking gender-affirming surgery. Their friendship grew through letters and meetings in London. In 1950, with her consent, Dillon performed an illegal orchiectomy on Cowell, an operation that enabled her to pursue further surgery with Gillies and legally register as female, making her Britain’s first known trans woman to do so.
Dillon’s affection for Cowell deepened into romantic hope. He wrote love letters and proposed marriage after his medical graduation, but Cowell declined, writing later,
“Although I liked and respected him very much as a person, there was no possible way I could ever think of marrying him.”
Their relationship, though short-lived, symbolised the fragile network of trust between early trans patients and the few doctors willing to help them. Both would later be recognised as pioneers, though their paths diverged dramatically.
Medicine, the Merchant Navy, and a Search for Meaning
After qualifying as a doctor in 1951, Dillon worked briefly in a Dublin hospital, where he introduced humane practices like occupational therapy, picnics, and patient libraries, echoes of Gillies’s holistic philosophy. He also donated a tenth of his salary to a fund for poor students.
In 1952 he joined the Merchant Navy, serving as a ship’s surgeon for six years on voyages to Africa, Asia, and the Pacific. The sea suited him: it offered discipline, anonymity, and constant movement. Yet even aboard ship, Dillon’s reading turned inward. He discovered the writings of mystics like George Gurdjieff and Tuesday Lobsang Rampa and began studying Buddhism seriously.
When his ship docked in India, Dillon travelled inland to Bodh Gaya and Sarnath, sites sacred to Buddhists. The simplicity of monastic life and the intellectual depth of Buddhist philosophy appealed to him more than the frenetic pace of postwar Britain. Gradually, he came to see medicine as only one kind of healing.
The Cable, the Title, and the Choice to Leave
For years Dillon had lived quietly as a man. But when he applied to correct the genealogical record in Debrett’s Peerage, noting his proper name as the younger brother of the baronet, a discrepancy arose. Burke’s Peerage still listed his birth name and sex. Journalists spotted the inconsistency, and in May 1958 the Daily Express confronted him while his ship was docked in Baltimore.
The ensuing headlines outed him to the world. Time magazine noted the contradiction between the peerage books and quoted the editor of Debrett’s: “I have always been of the opinion that a person has all rights and privileges of the sex that is, at a given moment, recognised.” Dillon maintained a polite fiction, telling reporters he had been born with a congenital condition corrected by surgery. But the intrusion shattered his privacy. He retreated into solitude, contemplated suicide, and finally resolved to disappear from public life altogether. He resigned his commission and booked passage back to India.
Buddhism and the Conquest of the Mind
In India, Dillon adopted a new name: Lobzang Jivaka, after the Buddha’s own physician. He donated his inheritance to charity and began living as a wandering scholar, first joining a Theravada monastery under an English monk, Sangharakshita. Their relationship soured, yet Jivaka produced important essays arguing that Buddhist monastic rules unfairly excluded so-called “third sex” individuals and that compassion demanded inclusion. His A Critical Study of the Vinaya (1960) was both scholarship and autobiography in disguise.
When Theravada monasteries rejected his ordination, Tibetan Buddhists in Ladakh proved more welcoming. In 1960, with the approval of Kushok Bakula, a Ladakhi prince, Jivaka entered the remote Rizong Monastery and became the first Westerner to be ordained there as a novice monk. Life was austere: the air thin, the food sparse, but the peace profound. “At home among strangers who were no strangers at all,” he wrote.
After three months, visa restrictions forced him to leave Ladakh. He returned to Sarnath, gravely undernourished and ill with typhoid fever, yet continued writing. His final work, Out of the Ordinary, an autobiography of gender and spiritual transformation, was completed on his forty-seventh birthday and posted to his literary agent.
Death and Legacy
Two weeks later, on 15 May 1962, Michael Dillon collapsed while travelling in northern India and died in a small hospital in Dalhousie. The cause was likely typhoid and malnutrition. His body was cremated in a Buddhist ceremony. His brother wanted the manuscript of Out of the Ordinary destroyed, but Dillon’s agent preserved it. It remained unseen until discovered decades later by journalist Liz Hodgkinson, who used it for her 1989 biography Michael née Laura.
In 2007, Pagan Kennedy drew on the same material for The First Man-Made Man. The autobiography itself was finally published in 2016 as Out of the Ordinary: A Life of Gender and Spiritual Transitions, restoring Dillon’s voice to the historical record.
His story reached television audiences in 2015 through Channel 4’s Sex Change Spitfire Ace, which chronicled the intertwined lives of Dillon and Cowell. In 2020, St Anne’s College, Oxford, launched the annual Michael Dillon LGBT+ Lectures to honour its former student and his contributions to science, ethics, and identity.
Dillon’s life bridged two kinds of healing — medical and spiritual — and his writings anticipated modern ideas about bodily autonomy and empathy in care. In the end, his journey from Oxford to Ladakh was less about transformation than about reconciliation: learning to live at peace in a world slow to understand.
Sources
Liz Hodgkinson, Michael née Laura (1989) — www.lizhodgkinson.com
Pagan Kennedy, The First Man-Made Man (2007) — archive.org/details/firstmanmademans00paga
Laurence Michael Dillon, Out of the Ordinary: A Life of Gender and Spiritual Transitions (2016) — Amazon UK
Time Magazine (1958), “Change of Heir” — content.time.com
St Anne’s College Oxford (2020) — st-annes.ox.ac.uk
Channel 4, Sex Change Spitfire Ace (2015) — imdb.com/title/tt6123958/
Scientific American, “The Surprisingly Old Science of Living as Transgender” — scientificamerican.com/blog/voices/the-surprisingly-old-science-of-living-as-transgender/
