The term “coming out” means different things to different people. Often, it’s about sharing sexual orientation. For others, it’s about embracing gender identity. For Jack Brennan, a longtime sports journalist and former Bengals public relations director, coming out meant peeling back decades of silence to share something deeply personal: his identity as a cross-dresser.
This fall, he’ll share his story in a big way — with a book he’s been working on since 2018: Football Sissy: A Cross-Dressing Memoir.
“Some parts of it are going to be a little icky to people, and I wonder what people are going to think,” he said. “But I did it the way they said to do it — open and honest — and I don’t regret it.”
A childhood in the closet
It’s easy to see why he wasn’t quick to share this side of himself. Cross-dressing and football rarely share the same sentence, let alone the same person, at least publicly. But Brennan is ready to talk about living both identities — spending his public life in the macho world of the NFL and his private life in heels.
“Sports fan” and “cross-dresser” are equally valid identifiers — both are integral to who Brennan is.
“Ever since I was, like, three-and-a-half years old, I had a tremendous attraction to cross-dress, and that was with me through all those years,” Brennan, who also identifies as queer, said. ”Behind closed doors, when I was a small kid, I would dig into my mother’s stuff. And then when I got older and left the house, I started getting the urge to get stuff of my own. It was very scary shopping for things, worrying I’d expose myself to humiliation and ridicule.”
For Brennan, cross-dressing is deeper than “playing dress up.”
“I just had this tremendous attraction to it,” he explained. “It was something I did strictly in private, but it brought me joy. It made me feel more like myself — even if I couldn’t share it with anyone.”
Brennan grew up in Dallas, Texas. While he was putting on dresses, he was beginning a respected career in the world of professional football and journalism. He studied journalism at the University of Texas and began his career writing for newspapers in Memphis. In 1983, his path led him to Cincinnati, where he took a job covering the Cincinnati Bengals for The Cincinnati Post. He later joined the Cincinnati Enquirer, where he covered the Cincinnati Reds’ 1990 World Series-winning season before returning to the Bengals beat. Brennan has also periodically written for CityBeat.
The Queen City would become home for his career, his family and eventually, his full self. But it didn’t happen overnight.
Telling his wife
He told his wife, Valerie, about his cross-dressing a year and a half into their marriage — about 50 years ago — while they were still building a life together that would eventually include three children and two grandchildren. The decision weighed heavily on him; at the time, he was terrified that he might end their relationship before it truly began.
“Many have said, ‘Well, gee, you didn’t even tell her before you got married,’” he recalls. “And no, I didn’t. I couldn’t do it. It was too scary. I was afraid it would bust up our engagement and ruin our relationship.”
When he finally did tell her, Valerie’s first concern was he would be fired if his bosses found out. Ultimately, she responded with love and grace. His secret life became something that was slowly accepted within their relationship, though it remained private to the outside world for decades.
How Brennan told the world
Brennan came out publicly as a cross-dresser in 2021 through a deeply personal feature published in The Athletic, written by his longtime friend and acclaimed sports journalist Joe Posnanski. Rather than a dramatic announcement, Brennan approached it with honesty and care, first telling a close circle of friends — especially male colleagues he had worked with for decades — before the story was reported.
He followed Posnanski’s advice to make a list of people he wanted to tell personally so they wouldn’t find out secondhand. These conversations, especially with longtime sportswriting peers, were emotionally difficult. Brennan feared rejection or judgment, but he was met almost universally with support and empathy.
“A person that I write about in the book is Bill Koch, my very good friend from The Cincinnati Post and the Cincinnati Enquirer,” Brennan said. “He was very shocked and stunned, and it took him a little while to come around. But he did, and everything is fine now.”
Putting pen to paper
It wasn’t just challenging for Brennan to share this deeply personal story. After deciding to write his memoir in 2018, he quickly realized that telling his story was just the first step — getting greenlit by a reputable publisher proved far more difficult. Brennan was determined not to self-publish, fearing that doing so might make his deeply vulnerable story seem like “just one weird person putting their secret on Amazon.” That led him to Cleveland-based Belt Publishing.
Choosing the title was another important decision. Initially, Brennan considered the clever but softer title Skirting the Norm, but after feedback from friends and family, he embraced the more provocative Football Sissy.
“For a white kid growing up in the 1950s in Texas, ‘sissy’ was the worst thing you could be called; the most humiliating and degrading insult,” he said. “I never faced that horror outwardly because I was comfortably masculine, but I knew if people found out about my secret, that’s what they’d say. I kind of co-opted the term to diffuse its power to hurt me.”
The NFL’s response
Brennan described the NFL’s reaction to his revelation as surprisingly progressive, especially given the traditional culture of professional football. While he never came out publicly during his 24 years working for the Bengals, he says the league office has long focused strictly on performance rather than personal life or sexual orientation.
He recalls the NFL’s support for Michael Sam, the first openly gay player drafted into the league, as a sign that the organization was ahead of many in embracing diversity.
“The NFL proclaimed itself a football meritocracy, meaning your sexual orientation wouldn’t affect your ability to succeed,” he said. “The league office was pretty — I hate to use this word, but — ‘woke’ compared to team owners, who tend to be more conservative. The NFL saw that being progressive was good for business.”
Though Brennan kept the secret from work, he said Bengals owner Mike Brown was ultimately supportive and understanding.
How Brennan’s piece fits into the LGBTQIA+ puzzle
Brennan acknowledges the challenges faced by the broader LGBTQIA+ community, especially in more conservative suburbs and rural areas. But his experience in Cincinnati has been largely positive.
“Cincinnati is where I have been for a long time, and, at its heart, the city of Cincinnati is still very accepting and tolerant,” Brennan said.
From Brennan’s perspective, the future holds both hope and concern. While he sees Cincinnati as a generally accepting and progressive city, he’s wary of the broader national climate that has sparked a surge in queerphobia and anti-LGBTQIA+ sentiment.
“I know a really nice family at church … they live in West Chester,” Brennan said. “They are — if you just looked at them outwardly — the ‘straightest,’ most ‘normal’ family. But one of their children is trans, and life is pretty damn hard for them right now with all these court rulings about gender-affirming treatment. It’s terribly, terribly hard.”
Brennan worries that the political climate is fueling needless trauma and division, but he also holds onto the belief that sharing stories like his memoir can chip away at bigotry and promote understanding.
“I don’t characterize my coming out as courageous or bold as a lot of other people’s coming out who have sustained a lot of trauma and needed more courage than I did,” Brennan said. “But everybody who comes out — me and anybody else who comes out in their own way — they’re one more stroke against bigotry and one more stroke for understanding.”
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.
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Jack Brennan’s Cincinnati Career
- 1983
Moves to Cincinnati to work for The Cincinnati Post, covering the Cincinnati Bengals - 1990
Joins the Cincinnati Enquirer as a sportswriter and covers the Reds’ 1990 World Series-winning season - 1991–1993
Returns to covering the Bengals for the Enquirer, continuing his close coverage of Cincinnati’s biggest football stories - 1994
Hired by Bengals owner Mike Brown as the team’s public relations director — a role he would hold for the next 24 years - 2017
Retires from the Bengals after a long and influential tenure - 2018
Begins writing Football Sissy - 2021
Comes out publicly as a cross-dresser in a feature article by longtime friend Joe Posnanski in The Athletic - 2025
On Sept. 9, Football Sissy will be released by Cleveland-based Belt Publishing
This story is featured in CityBeat’s July 9 print edition.
This article appears in Jul 9-22, 2025.