Football Sissy

By Jack Brennan
August 19, 2025

In Jack Brennan’s decades-long career as a sports journalist, he covered teams like the MLB’s Reds and the NFL’s Cincinnati Bengals before becoming the PR director for the Bengals. He wrangled sports stories, reporters, and players. At home, he played basketball with the neighborhood husbands and raised three kids with his wife, to whom he was devoted. At the same time, he had a passion that never left him: he liked dressing as a woman. Blonde silky hair, bright lips, smooth legs escaping short skirts, ending in heels as high as they go. 

While he kept his life as a crossdresser private, eventually his world opened up, and he came out publicly via The Athletic in 2021. Football Sissy offers a view of his dual lives, and the slow build of his decision to become one of the first men in the NFL to come out as LGBTQ+. The story follows his childhood experiences, the thrills of his career, the messy entanglements he got into (including being accosted by the police for breaking into his own home), and his coming to terms with his own biases and misapprehensions.

Told with the characteristic humor of Brennan’s sports columns, Football Sissy is a riveting inside peek at life inside the NFL, and a heartwarming tale of acceptance and love, even within the most masculine environments. 

---

Jack Brennan worked forty-four years in sports. As a journalist for multiple papers in Cincinnati, including the Cincinnati Enquirer, he was beat writer for both a Reds World Series winner and a Bengals Super Bowl qualifier. As public relations director for the NFL Bengals, he and his staff won the 2006 Pete Rozelle Award, conferred by pro football journalists to the league’s top PR staff. Brennan grew up in Dallas, where he played low-level high school football and held his own Cowboys season tickets. He is a 1973 graduate of the University of Texas and has been married fifty-one years to his wife, Valerie, with three adult children and two grandchildren. Brennan enjoys tennis and other vigorous physical activity, he is active in progressive causes, and his favorite reads are very thick histories and biographies.

5 X 7 | PAPERBACK