He was 3-and-a-half years old. In fall of 1955, Jack Brennan desperately wanted to try on a neighbor girl’s blouse with “the cutest puffed sleeves.”
Brennan, the former Cincinnati sportswriter turned Bengals publicity director, recalls the day he first put on women's clothing in his new book, Football Sissy: A Cross Dressings Memoir, released today by Belt Publishing. (He’ll talk about the book and sign copies at JosephBeth Booksellers 7 p.m. Tuesday, Sept. 9.)
He was mesmerized by the girl’s top while they were playing in her bedroom.
“I wanted to know what it would feel like to wear it . . . I wanted to experience it. I wanted to gaze at a new self in the mirror and then put on a complete girl’s outfit and be seen in it by others,” he writes in the chapter called “Yes (Lady Gaga), I Was Born This Way."
His book describes his secret cross-dressing experiences as a sportswriter in Texas, Memphis, and writing for the Cincinnati Post and Cincinnati Enquirer, where he covered the Bengals 1989 Super Bowl and the Reds wire-to-wire World Series in 1990. He left the paper in 1994 to work for 24 years as the Bengals’ press box boss.
Brennan came out as a cross-dresser in 2021, after retiring from the Bengals, via an article in The Athletic by his former Post sports writing colleague, Joe Posnanski.
”We don’t feel we were born in the wrong body, we just want to wear the wrong clothes, not 24/7, but regularly,” he writes in Football Sissy. “I want to be mistaken for a glamorous and totally made-up Fox News anchor babe. I want to be desired by men,” he writes.
Until he started writing the book, he didn’t even tell his best friend, Bill Koch, the author and former Enquirer and Post sportswriter.
“I always had a public-facing job in very masculine fields,” he writes. “I feared an existential loss, therefore forfeiture of male camaraderie. Lunches, tennis and a few beers would never be the same, if they continued at all . . .
"I was a closeted cross-dresser, a guy with a visceral urge to play-act as a woman in skirts and heels and makeup. Queer men like me were presumed not to exist in the NFL world, particularly in a team’s ‘football side’ jobs, the ones requiring daily contact with half-dressed or undressed players in locker rooms and clubhouses. The air was heavy with an unspoken implication that in the NFL inner sanctum, queers should not exist.”
As a sportswriter, he discovered he could pack two sets of clothes for road games — clothes for working at the stadium, and women’s clothes to hit the bars at night. He lost that opportunity when he joined the Bengals front office. But he continued to dress up and hang out at a couple of bars near his Clifton home, the Golden Lion, and Arlin’s Bar & Grill.
His wife Valerie — they’ve been married for 52 years — worried the Bengals would fire him. “I worried about it sometimes, but I was not going to stop. I did it when I wanted to do it, mostly. Tried to be careful, tried to be discreet,” he told Lucy May on WVXU-FM’s Cincinnati Edition Sept. 3. Hear the entire 26-minute interview or read the transcript here.
“I wanted to make it public, for the same reason, I think, that most everybody else who has come out as queer in some fashion wanted to make it public, to just say, ‘I'm not scared, I'm going to come out.’ And hopefully this might make some other people feel better, and every person who comes out does their own small part to spike bigotry and prejudice. So certainly, I had that incentive, just like so many other people have,’ he said on WVXU.
Brennan tells me that Football Sissy is for “any queer person who might be heartened by another coming-out story. "It's for people who might have thought that a queer couldn't have a measure of success with a career in football. It's for anybody who has had a secret they didn't feel they could share with anyone else. It's for fans who enjoy some insider insights into the NFL.”
Bengals President Mike Brown “has been supportive all the way,” Brennan says. Peter King, the former Enquirer sportswriter who covered the NFL for Sports Illustrated and NBC Sports, suggested that Brennan give former Bengals stars Cris Collinsworth and Boomer Esiason a head’s up about the book. Collinsworth, Esiason, King, Posnanski and former CBS analyst Phil Simms wrote blurbs for for it.
King wrote: “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.’ ”
“There’s a toll from spending every day since age 3 — the first time I felt the urge to cross-dress — with background worry about who might find out,” Brennan says. “No human should have to carry that baggage of shame.”
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