Jack Brennan worked for decades in Cincinnati. He was a sports reporter for the Cincinnati Post and then the Cincinnati Enquirer before he became the public relations director for the Cincinnati Bengals.
All were public-facing jobs in masculine, male-dominated fields.
And all the while, he had a secret. He was a cross-dresser.
Brennan writes about his life and how he decided to go public in his new memoir, “Football Sissy: A Cross-Dressing Memoir.”
On Cincinnati Edition, we talk about the book and his experience working in the NFL.
A transcript of this discussion is below.
This episode was transcribed using a combination of AI speech recognition and human editors and has been lightly edited for clarity. It may contain errors. Please check the corresponding audio before quoting in print.
Guest:
- Jack Brennan, author, “Football Sissy: A Cross-Dressing Memoir”
Joseph-Beth Booksellers will host a book signing with Brennan at 7 p.m. Sept. 9.
Ways to listen to this show:
- Tune in live at noon ET M-F. Call 513-419-7100 or email talk@wvxu.org to have your voice heard on today’s topic.
- Catch the replay on 91.7 WVXU and 88.5 WMUB at 8 p.m. ET M-F.
- Listen on-demand. Audio for this segment will be uploaded to this page by 4 p.m. ET., or subscribe to our podcast.
Your book is called "Football Sissy." You acknowledge that "sissy" is a term that many people find offensive. Why that title?
Yeah, I've gotten a lot of questions about that, and I think everybody agrees the title has punch. I write about that a little bit in the book, a very dear friend of mine who's gay said, "Oh, I just hate that word. I wish you wouldn't use it." He said it's been used against me in my life, and it just is painful. I never had it used against me because I was always passing as passably male, especially when I was younger. But still, I knew that if people knew what I did, I would be called a sissy, which was about the worst thing you could be called in 1960s Texas as a young boy. So I think I kind of took it on and co-opted it to try to make sure I can stand up to it, maybe take away a little of its power. At one point the title of the book was going to be skirting the norm that was suggested to me by a friend, and I thought it was clever.
When did you first realize Jack that you like to dress in women's or girls clothing?
Three-and-a-half years old, visiting a little with my mom visiting some neighbors who had a daughter about our age. She was wearing a little blouse with puff sleeves, and it just attracted me, and I wanted to wear it. And so we swapped tops. At that point, I kind of knew, wow, this is pretty strong feeling here that I can't ever share with anybody, ever.
How different is what you do from drag? Or is it?
I'll bow to anyone else's superior understanding of it. In my understanding, drag performers are not really looking to pass as a female. They are wanting to boldly and fearlessly express a feminine look and persona, but are still male, whereas cross-dressers, I think, or at least I did, always just wanted to really be and look like a woman and feel like a woman.
Did you ever feel shame about that as a kid or as you got older?
Only transitory moments. I'm very thankful for this, and I give my parents a lot of credit, just not my parents did not ever know about me, but they were good parents, and they gave me a good self concept. I never felt that really when it mattered. Bottom line, I wasn't any more screwed up than the than the average person. I accepted myself pretty well all through life.
You mentioned your mom and dad. Tell us about your relationship with your parents and if that shaped your interest in dressing, or your feelings about it.
I don't perceive that it really did. I just again, I just think they were good parents that imbued me with a good self concept. My mom was the more communicative one that I spoke to more often at length. My dad was not a real touchy-feely, huggy guy, but I knew he loved me and he was fun to be with. He really sparked my lifelong love in sports. We played softball in our backyard. It was the neighborhood softball spot, and he kind of ran that. He had a job where he had some connections, and he could get tickets in Dallas to big football games. And so he was always just fun to be with. I guess that sums it up. Neither one of them, I don't think ever had a remote clue that I was a cross-dresser.
Your dad had a bit of a family secret though, too, didn't he?
Yes, my dad was suffered from severe alcoholism, and he died when he was 66. It was very sad. And you know, it was sad all along. High school is when he started to become a real problem to himself and my two older siblings were already out of the house. Then I just kind of decided to myself, OK, this is really seriously sad and bad, but I'm not going to let it dominate my whole life. People, other people have big problems too, and they deal with it and they they move on. They don't let it define their life. So I did a pretty good job of that also, I think.
Well, and you mentioned that, you know, you never talked to your parents about your cross-dressing in any way. But am I remembering correctly from your book that sometimes you did kind of sneak some of your mom's clothes?
Oh, yeah, she was my first source of clothes, lingerie, and nylons, and makeup. She wasn't a big fashionista person, but she had plenty of stuff that interested me.
Well, I know you kept this a secret for many years, even from the woman you love, the woman you eventually married. When did you decide to tell your wife, and how did that go?
I met Valerie when we were seniors in high school, and at that time, I had kind of put cross-dressing away. I didn't want that to define my life. I did want to have a relationship with a woman and get married and have a family. We met in November of our senior year in high school, and by that summer, we had pretty much pledged that we were going to get married when I got out of college. So all that time, and then even when it started cropping up again, I was just like, well, I can't and people do ask that question, they go, gee, you didn't tell her before you got married. I just couldn't do it. I was 21 years old. I was afraid, and I think maybe justifiably so, that if I came out before the wedding, it would blow everything up and just devastate two families. So I just didn't do it. But once we were married, then pretty quickly, the tables kind of turned, and I realized, well, you can't keep this a secret for your whole life from your wife, come on, you're just not going to be able to do that. We were just laying in bed one night. The idea had kind of been on slow burn with me, and so I just told her. She was very gob-smacked by it, not happy to learn it. We hashed it out for a while. Finally agreed, both in tears at one point, finally agreed that there was no sense staying up all night talking about it, so we went to sleep side by side with one another. The one thing that made me feel good was that never once in our discussion did the idea of us breaking up come up, and I know that just from personal experience and anecdotes that many marriages have broken up over the issue of cross-dressing. Very fortunate to have found such a great wife as Valerie, and I think we just click for each other. Our relationship has not been perfect or a fairy tale, but it has been very real, and we're in year 52 now.
Jack, you had a career in journalism as a sports reporter, as I mentioned — were you worried about what would happen with your job if someone found out you were a cross-dresser?
I worried about it more after I left sports writing and joined the Bengals. That was a great job, a tremendous opportunity — I would never, ever regret taking it. But in my heart, I was always still a writer and a sports writer. And Mike Brown knew that when he hired me. In the newspaper business, I didn't have much worry — you know, fairly liberal, open business, even though, certainly, like I've said in in the media that covered the NFL that I was with, there was nobody that was openly queer. Valerie worried, especially after I worked for the Bengals, that I would get fired. And I never thought I would get fired, but, I did worry if it went down the wrong way with the wrong coach or something, that I would have been reassigned from my duties, which had me frequently in the locker room and embedded with the actual football team at all times. So that was a worry, and 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 very discreet.
I asked about the reporting, because it seems like in your book, the trips to cover games did offer some opportunities for cross-dressing.
Well, mostly the summer that I was on the Reds beat, but on the baseball beat, where you would spend a few days in a city, rather than the in and out of football travel, although I did it on some football trips too. Anyway, I would bring a whole trove of clothes and shoes and stuff with me, along with all my reporting stuff, it's hard to even believe that I did that — all the trouble that that would have been, but I did it.
You retired from the Bengals in 2017. When and why did you decide to come out as a cross-dresser more publicly? I know by that time you had told a small circle of people.
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.
But also I wanted to write a book. I wanted to write a good book. I feel like I'm a writer at heart. I get a lot of satisfaction out of writing something, and people telling me they enjoyed it. Wanting to write the book was tied in with why I decided, or obviously, if you're going to write a book about it, you're coming out. And I started to write the book, and I'd think, oh, what's it going to be like when I actually, really do have to come out? Well, don't worry about that. Now, you're not even halfway finished writing the book, yet. You can worry about that when the time comes.
From talking to people, a couple people close to me, I do have the sense that a lot of people come into this knowledge of this book, and they go, why? Why did you want to write this? Why do you have to write this? And I go back to my very dear brother-in-law, the husband of my very dear sister. He's a little bit of an older guy. He grew up in a pretty conservative life, and my sister was a big, big booster of the book, and we were visiting them at their house when it kind of first came out that I was going to do it. He said, "I'm not sure why you're telling me this." He said, "Do we have to tell everybody everything about ourselves? Maybe, maybe some things are better not told." I think I said he was half pissed off and half crest fallen. I love him to death. His name is Frank. My sister is Andrea. They've been so great. This was kind of a good practice session to answer this question, I just said, "You know, Frank," I said, "if I'm willing to own this part of myself, then if you're truly close to me and we have a close relationship, you can't ask me to hide it." I said, "What if you ask me, how was my weekend? Well, if my weekend had included cross-dressing, am I supposed to lie to you or be evasive?" He quickly came around, to his credit; you're right. That doesn't work, because I was willing to open up and be vulnerable to him. It deepened our relationship.
In the end, so many times back and forth, I've learned from other people and whatever, that if you are vulnerable and open yourself up to another person, you will get it back in kind. They will feel comfortable opening up and being more real. Also, some parts of this book are probably going to make some people uncomfortable, but that's the why of it. That's that. That's why I did it.
I know this book has been years in the making. The first kind of public acknowledgement that you made was in 2021 in The Athletic. Soon after that, former Enquirer columnist Paul Dougherty wrote about it. His editors wanted him to. He said he didn't want to at first, but he did, and in the column, he asks, Why am I even doing this? What business is this of anyone's? And some of the comments on that column of his were pretty ugly, but you write in the book that there was one comment that really made you smile. Do you remember that one?
He did that story the day after the one in The Athletic came out. For The Athletic story, they disabled the reader comment function for reasons I guess people can speculate on but the Enquirer did not disable that. And so there were, I think maybe, like 30 or 35 comments. About half of them were supportive, and the other half were pretty snarky and mean and disparaging. But the one I liked near the end was a woman reader. She said, "Paul, Paul Dougherty." She said, "Paul, you had to know when you wrote this that all the insecure men would come out of the woodwork." So that made me feel good.
We've kind of talked about this a little bit, but men's sports in general, the NFL especially, are seen as such masculine places, there haven't been many NFL players who have come out as queer in any way. Male cheerleaders from the Minnesota Vikings earlier this year have outraged some fans. I mean, fans have been throwing sex toys on the court during WNBA games. When these kinds of things happen, when people exhibit these behaviors, what does it mean to you about sports?
I never found the NFL or the Bengals to be, like, rabidly queerphobic, but yet it was just implicitly assumed, especially people, like, what they call football job, football side jobs of the franchise that I had, it was just in the ether that nobody was queer. One of my lines I'm proud of in the book, I said was the assumption that you were straight was no less implicit than that you hailed from Earth instead of Mars. It wasn't a real oppressive or hard place to be. The NFL office was pretty progressive on social issues of all kinds. Mike Brown, he's a Republican, he's a conservative, but he's not a big in-your-life guy on social issues.
You came out in 2021. There's still this anger that's happening with these male cheerleaders. There's this behavior happening at WNBA games. Does that surprise you? I mean, would you have thought there would be more people coming out as queer or different behaviors being exhibited at this point?
It has been pretty slow. I remember when I was doing some freelance writing for City Beat. I got a hold of Jason Collins. He was the first athlete to come out as gay while he was still active in a major sport, he was an NBA player, not a star. He was on the tail end of a long career as a reserve player, but he did come out, and he was the very first one, I reached him for this article just about inclusion in sports, and he said it was very disappointing to him that no one else had come out. I don't think anybody else has held a job like mine. Again, a football side job, media relations, trainers equipment managers, travel managers, I don't think anyone else has come out, and and certainly not while they were working. And I was not willing to come out while I was working either. And of course, the climate in the country today, turning the clock back on tolerance and inclusivity probably going to stay worse for a while, until we can get the country back on a better course.
Does the political climate ever give you second thoughts about the decision you made?
Yes, but only for a moment, because you just can't not come out and do it, whatever the danger might be. Much more miserable feeling like you have to hold it in.
You and your wife have been married for a long time, 52 years. You have three adult children who all know about your cross-dressing. How has your coming out affected your family, or has it affected your family?
Not too much. Everybody has been supportive, accepting and then supportive of the book. Now we don't spend a whole lot of time and the family talking about my cross-dressing, that still maybe is a little bit uncomfortable at times, but everybody knows it. Nobody runs from it. Maybe you'd have to ask them and the family, but no, I think we've carried on quite well. The support for me, just show me that they have a broad based love for me, just as I do for them. And I think they're proud of me in some fashion.