Photograph by Devyn Glista
Jack Brennan is not the first person connected to the National Football League to shave his legs and put on women’s clothing. In 1974, New York Jets quarterback Joe Namath famously wore pantyhose—but only for a Hanes Beautymist TV commercial. Whereas for Brennan, red lipstick, Jessica Simpson brand pumps, and two waist-cincher corsets are just part of who he’s always been. In secret.
A former Cincinnati Post and Cincinnati Enquirer sportswriter who later spent more than 20 years as PR director for the Cincinnati Bengals, Brennan didn’t come out as a cross-dresser until a 2021 interview with The Athletic. Now, he’s telling all in his new memoir, Football Sissy.
It is unique both because of Brennan’s time spent in the super-masculine, conformist world of football—the NFL is barely a place for independent thinking, let alone unconventional gender expression or sexuality—and because of his particular LGBTQ+ identity.
“I don’t identify as gay,” Brennan says. “I do identify as queer.” He’s a cross-dresser, not a drag queen, nor is his experience the same as a trans or non-binary person. “I never felt I was born in the wrong body. I just wanted to wear the wrong clothes. And not all the time, but regularly.”
Brennan stayed closeted for many years, while navigating a bumpy don’t-ask-don’t-tell arrangement with his wife. The book’s opening scene foreshadows a close call of his secret getting out to others, including the Cincinnati Police Department. At the same time, during all those years, he almost never had an issue trying on clothes in women’s dressing rooms at department stores or using the women’s restroom at his trusted local bar when out “en femme.”
The book also features what amounts to practical cross-dressing advice and style tips on everything from eye makeup to the use of breast forms as a way to provide additional insight and illumination into Brennan’s life.
A good memoir has to be forthcoming. Once Brennan had an editorial team, he was pushed to share even more, including a deeper dive into the sense of fantasy and thrill he gets from dressing. The book is not especially racy, nor at all prurient, but “they said you gotta let it all hang out and just be as honest as you can be,” Brennan says. “Like, ‘C’mon, give me some more. Dig some stuff out!’ And I was like, ‘Oh all right. I’ll write about that too.’”
There are a few dramatic or explicit anecdotes that Brennan concedes might give some of his family members pause, including a few moments not included in earlier drafts (most of them have read the book). But that’s not necessarily specific to him being queer. “Nobody likes to think about what their parents or their grandparents have done in very personal times,” he says. “But I don’t have any question that that my family will all be supportive.”
Brennan has already done the hard part: coming out to his friends and relatives privately, and going public via The Athletic. He did that interview in part to catch the eye of editors and book agents. “Also, it just seemed like the right thing to do,” he says.
“It’s not going to cause a revolution, but I hope that the story can do its one little part, just like every other person to come out has done their one little part, to spike misunderstanding and prejudice.
“I found through this process that when you are not afraid to be open and vulnerable with people, they respond in kind, many, many times.”
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