A former sports journalist and PR director for the Cincinnati Bengals is sharing his story of being one of the first men in the NFL to come out as LGBTQ+ in a new book, Football Sissy: A Cross-Dressing Memoir.
Jack Brennan had a decades-long career reporting on teams like the Cincinnati Reds and the Bengals before becoming the Bengals’ PR director. At work, he wrangled sports stories, reporters and players; at home, he played basketball with other husbands in the neighborhood and raised three children. All the while, he had a secret passion: He liked to dress as a woman.
Cross-dressing was a secret Brennan wouldn’t share until a 2021 article from The Athletic in which he officially came out.
“I feel like I want to become more genuine to people around me and not hide anymore. And maybe, I don’t know, someone else will see this and it will help them,” Brennan told sports journalist Joe Posnanski at the time.
Football Sissy offers a look at Brennan’s dual lives and the slowly building decision to come out as LGBTQ+. The book follows his childhood experiences; the thrills of his career; and some messy entanglements, including being accosted by the police for breaking into his home, all while he faces and comes to terms with his own biases and misapprehensions. Brennan tells his story with the characteristic humor of his sports columns and an overall message of acceptance and love, even in the most traditionally masculine of environments.
“Football Sissy traces a fascinating path through two lives—one public, one intensely private. I hope Jack telling his story helps five, ten, twenty-five people in the macho orbit of professional sports to think, ‘It’s okay to be different—and I’m not going to live in the shadows anymore,’” writes four-time National Sportswriter of the Year Peter King.
Football Sissy: A Cross-Dressing Memoir is being published by Belt Publishing and will hit shelves on Sept. 9. Learn more about the memoir at beltpublishing.com.
This article appears in Mar 5-18, 2025.
