We have read countless memoirs of people who crossed boundaries of race, class, or nationality, but far fewer who have written so openly about crossing the most intimate boundary of all, the line of gender. In Crossing: A Memoir (1999), the distinguished economist Deirdre Nansen McCloskey recounts her journey from living as Donald, a “golden boy” of conservative economics, to becoming Deirdre, a woman who not only transitioned but thrived in the academic world despite formidable challenges.
McCloskey’s story is not simply a tale of surgery and hormones. It is an intellectual memoir, a cultural critique, and a deeply personal reflection on what it means to live authentically. It asks fundamental questions about identity, gender, and society’s response to those who break its most rigid categories.
Born in Ann Arbor in 1942, Donald McCloskey seemed destined for a conventional path of academic success. He earned his AB and PhD in economics from Harvard, studied under the eminent Alexander Gerschenkron, and quickly rose through the ranks at the University of Chicago, where he helped shape the cliometric revolution in economic history. His book The Applied Theory of Price became a cornerstone of Chicago Price Theory. Yet beneath this professional triumph, another story was unfolding, one of secrecy, longing, and struggle. Married for three decades and a father of two, McCloskey hid her gender dysphoria from nearly everyone. In the conservative academic world of the 1970s and 80s, the idea of transition seemed unthinkable. “If I had told my parents in 1953, they would have put me in a madhouse,” she later recalled.
Her memoir captures the awkwardness and joy of this learning process. She describes herself in those early years as “like a 14-year-old girl trying on different looks.” Over time, she settled into what she calls “sober but elegant clothing,” finding comfort in her new identity while retaining her academic seriousness.
McCloskey’s memoir is also a record of loss. While she kept her tenured professorship and continued publishing prolifically, her personal life was torn apart. Her wife of thirty years and their two children rejected her transition. “My marriage family turned against me, never relenting in the 21 years since then,” she told me. “My two children have not spoken to me. I have three grandchildren I have never seen.” Even more painfully, her sister attempted multiple times to have her institutionalized. “She succeeded twice, in having me seized by the police and placed in a madhouse,” McCloskey recalled. These episodes highlight the profound risks trans people face, not only rejection but also legal and medical abuses at the hands of family or institutions. And yet, despite the grief, she remains clear: she would make the same decision again. “Even if I had known that my wife and children would reject me, I would have gone ahead, sad but determined.”
What keeps Crossing from being weighed down by sorrow is McCloskey’s humor and intellectual curiosity. The cover photo, showing her laughing heartily, captures the spirit of her narrative. “I think I was laughing at some gentle criticism from the audience,” she told me about that moment, which took place during her 1999 presidential speech to the American Economic History Association. “If you don’t have a pretty good sense of humor, I advise against crossing gender!” That sense of humor pervades her writing, softening the hard edges of rejection and allowing her to reflect with wisdom rather than bitterness. She embraces the contradictions of her identity, “a literary, quantitative, postmodern, free-market, progressive Episcopalian, Midwestern woman from Boston who was once a man.”
McCloskey situates herself within a lineage of trans pioneers. She speaks warmly of Katherine Cummings, the Australian librarian whose Katherine’s Diary inspired her, and of her friend Susan Marshall, a former Royal Navy commander turned Oxford bursar. She also cites Jan Morris’s Conundrum, a groundbreaking transition memoir, as a source of inspiration. These women, she notes, were not just trans women but accomplished professionals, writers, administrators, scholars, who lived full lives beyond their gender. McCloskey herself has become such a figure for younger generations, proving that transition does not mean the end of intellectual or professional achievement, but can mark the beginning of an even fuller life.
While Crossing is deeply personal, it is also social commentary. McCloskey challenges the medical and psychiatric gatekeeping that trans people faced in the 1990s (and often still face). Her decision to undergo gender reassignment surgery in Australia was partly strategic: outside the U.S. or Netherlands, she could avoid psychiatrists and her sister’s interventions. She also reflects on how society views transgender people. In the 1980s, trans women were depicted in popular culture as dangerous or freakish.By the late 1990s, representations began to soften, with films like To Wong Foo, Thanks for Everything! Julie Newmar and television coverage by Oprah Winfrey. “It’s how real social change happens,” McCloskey told me. “Pop culture is where we do our thinking as a society.” Her memoir thus documents not only her personal transformation but also a turning point in cultural perception.
Two decades after its publication, Crossing remains a landmark in transgender literature. It paved the way for later memoirs that are now part of mainstream culture, from Janet Mock’s Redefining Realness to Jennifer Finney Boylan’s She’s Not There. McCloskey’s voice stands out because she straddles two worlds, one of economics, rhetoric, and intellectual debate, and one of deeply personal transformation. Looking back, she admits regret only about timing. “I would have preferred to have transitioned in 1953, at age 11,” she said. “That way the male secondary characteristics would not have developed. But in 1953, there was nothing to be done.” Yet she also recognizes the gift of having lived two lives: “I had the experience of a full life as a man… and now I have a pretty full life as a woman.”
Crossing: A Memoir is more than one woman’s story. It is a meditation on authenticity, resilience, and the price of truth. McCloskey’s lessons are clear: attend to appearance and gestures, but don’t obsess over surgery; get on with actual life as a woman rather than becoming a “professional trans woman” unless that is truly one’s calling; keep a sense of humor; and remember that social progress can always be reversed if vigilance is not maintained. Today, McCloskey continues her work as an economist, historian, and advocate of liberalism, holding the Isaiah Berlin Chair at the Cato Institute. Her scholarship and memoir together form a rare combination: the rigorous analysis of a world-class economist and the vulnerable honesty of a woman who crossed the deepest boundary of identity. For anyone grappling with questions of gender, identity, or authenticity, Crossing offers not only a story but also a challenge: to live truthfully, even at great cost, and to embrace life with humor, resilience, and dignity.
Available via Amazon
Photo via The Heroines of My Life
Other related sources:
Post a Comment