Football Sissy

By Jack Brennan
September 9, 2025

"This is fearlessly honest stuff from a great human who went through things I never knew about. I admire him all the more for telling this story." —Phil Simms, Super Bowl XXI MVP

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. As the public relations 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, and smooth legs escaping short skirts, topped off with heels as high as they go. 

He kept his life as a crossdresser mostly private, so his public coming out via The Athletic in 2021—one of the first men in the NFL to come out as LGBTQ+—was a surprise to many. Football Sissy offers a no-holds-barred trip through his dual lives, from his earliest love affair with a puff-sleeve blouse at age three through to his first jaunts dressed in public to surprise visits to the hospital alongside a fulfilling family life and an exciting career.

Told with the characteristic humor and ease of Brennan’s sports columns, Football Sissy is a heartwarming tale of acceptance and love, even within the most masculine of environments. 

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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.

Advance praise for Football Sissy: 

"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.'" —Peter King, four-time National Sportswriter of the Year

"Back in his football days, Jack Brennan was perpetually the most delightful person in the room. None of us knew that he had a secret that he was deathly afraid to share. Now, in his own inimitable, hilarious and courageous style, he's sharing that secret and letting us inside his world and the world of professional football." —Joe Posnanski, author of New York Times bestseller The Baseball 100

ISBN: 978-1540270047 | 6 X 9 | 240 pp | PAPERBACK