As we sat in his backyard – not far from the scene of the suspected crime, which we’ll get to later – we eventually got around to what he called his all-time favorite Hall of Famers.
If you’re thinking Anthony Munoz, Ken Riley and Paul Brown, the three Bengals enshrined in the Pro Football Hall of Fame – you are wrong.
No traditional gold wool jacket for him.
His Hall of Fame wear includes:
- A lipstick-red faux leather jacket with a cropped waist and several shiny silver zippers.
- White denim cutoffs with what he said were “wild splotches of color all over.”
- Jessica Simpson black patent leather stiletto pumps
If those wardrobe items weren’t quite what you expected – after all Brennan always seemed to have more in common with rumpled Oscar Madison than refined Oscar de la Renta – then you’ll be surprised by what else he kept in the closet for most of his life.
For close to seven decades – going back to when he was just 3 years old – Brennan has loved to cross dress.
He loved wearing women’s clothes.
That’s when Jack became Jackie.
It was his tightly kept secret, one he initially shared with no one.
He eventually told Val after they married in December of 1973. Over the ensuing years he shared his predilection with a few others including their three children.
No one from the flip side of his life, be it the Bengals organization, the NFL or those of us who spent countless games with him in the press box – he worked 467 of 468 Bengals games when he was with the team – had an inkling his game day khakis and sports coat were just necessary props.
I’ve known Jack for close to four decades – known him for his gags, his kindness, his professionalism, his loyalty and friendship – and yet I didn’t know him.
Neither did his closest pals, guys like fellow sportswriters Bill Koch and Todd Jones and a few others.
Brennan led a dual life that immersed him in the macho world of pro football by day, and transformed him afterward when he dressed femme and presented female.
The secrecy, the fear of discovery, the denial of true self took a private toll until he finally got the opportunity – and the courage – to free himself.
After he retired from the Bengals, he told his story to a talented sportswriter friend – Joe Posnanski of The Athletic – whose piece on Jack came out in early February of 2021.
With the reveal, Brennan – who embraces the word queer and describes himself as “a queer man” – became one of the first men in the NFL to come out as LGBTQ+.
Before Posnanski’s story was published, Brennan wanted to break the news to the people he’d worked with and been closest to for so many years.
He knew his longtime boss, Bengals owner Mike Brown – the man he sat and talked with almost every day – needed to hear from him first.
“I wasn’t sure how he’d react, but he knew me well and I considered him a friend,” Brennan said.
He said Brown responded with the kindness he’d hoped for and then surprised him as he told of the respect he had for Jan Morris, the transgender Welsh journalist who scaled Mount Everest.
As for Brennan, he stumbled trying to scale the misapprehensions he had about others and sent evasive emails to Boomer Esiason and Cris Collinsworth, the Bengals stars he once dealt with.
Without adding any specifics, he told them an article on him was coming out and he wanted them to be prepared. Both were mystified and feared the worst: Was he sick? Was his family OK?
They reached out quickly, but when they heard the news, they chided him for not being frank and believing in their friendship.
Then they both embraced him.
Brennan sent some of the rest of us emails too and I remember my response back:
“I hope you have more style when you dress than what I’ve seen from you as a guy. Our whole profession has a bad reputation there, so I hope you’ll lift us up. But you’re my pal, heels or no heels.”
Brennan said one lesson he learned from all this was: “Your true friends are your true friends and something like this isn’t going to change that.”
A day after Posnanski’s column appeared, Enquirer columnist, Paul Daugherty wrote a supportive piece topped by the headline: “My Friend Can Wear What He Wants.” It was followed by a smaller subhead: “Jack Brennan Says He’s a Cross Dresser. So What?”
When the story was posted online, several, mostly-anonymous trolls answered the “So What?” challenge with vitriol.
One called Brennan a “pervert” and another said “weirdo.”
Someone said the story made them ill and another surmised: “This must be very embarrassing to the Bengals and very sad for his family.”
Unnerved by some of the comments, but undaunted in his effort to be himself, Brennan is about to forever discard all secrecy, hesitation and email evasion.
On September 9, Belt Publishing will release Brenan’s brutally honest, sometimes funny, often vulnerable book, entitled:
“Football Sissy: A Cross-Dressing Memoir.”
The cover features a tube of pink lipstick that looks as if it’s setting on green football turf.
Brennan said he almost went with a friend’s suggestion for the book title – “Skirting the Norm,” – but said he realized he wanted something with more punch and came up with “Football Sissy.”
“Oh, I know the word can be such a powerful, derogatory term, and I know how very humiliating it can be,” he said. “But if you take ownership of the word, you can’t be hurt by it.”
He often self- identifies as being a “sissy.”
“The final vote for it came from a friend of my daughter, Hannah,” he said.
“She said, ‘If I saw the title Skirting the Norm, I might pick the book up and I might not. But if I saw this book - with the new title and the cover – I’m picking it up and at least looking at it. I’m going to see what it’s about!’”
Dual life
Brennan grew up in Texas and said he was just three when he first felt an urge to cross dress.
His mother had taken him on a play date to the house of a little girl named Janie. As they played in her bedroom, he became obsessed with the puffy sleeves of her blouse and convinced her to change shirts with him.
The pair ran out to show their mothers and drew a laugh. He still remembers the exhilaration he felt and how he didn’t want to give back the puffy sleeved shirt.
He’d end up going to a Catholic grade school, playing sandlot football with his buddies, spending his money on football and baseball cards and then playing high school football.
He met Val his senior year of high school and as their relationship grew, he went to the University of Texas, joined a fraternity and planned to marry her right after college.
And yet through it all he ventured into his dual life whenever he could. When he was 12 he would put on his mom’s lingerie in the bathroom.
Sometimes during classes he slipped out to the restroom, put lipstick on and for a minute or two admired his image in the mirror before quickly wiping it off and returning to his studies.
At his college frat house, he remembers slipping away from the crowd to his room and donning a bra he had secreted away.
Although he said he knew he should tell Val about his cross dressing before they married, he feared it would wreck their wedding plans.
He stayed silent until some 18 months later when they were lying in bed one night and she was about to fall asleep.
She was stunned and hurt and angry and for a while felt cast adrift.
They talked through some of the issues – she said she wished he didn’t cross dress – and for a long time after it became a “don’t ask don’t tell” deal with her.
“Never though did it rise to the level where it threatened our relationship,” he said.
They tried dealing with it several different ways, including once when he went to conversion therapy.
That psychologist had him envision wearing women’s clothes and being covered, head to foot, in feces.
Even Val agreed crap like that was going too far.
Once Jack started working for the Bengals she worried the team would find out and he’d be fired.
He said he believed in the goodness of Mike Brown and thought he wouldn’t be canned, although he might end up being reassigned because players and coaches might not understand.
He said the dressing room was never an issue for him and I worked alongside him in there for decades and believe him. Like with women reporters in those quarters, he had a job to do, and he did it as a pro…not a voyeur.
In later years, he mostly dressed up and went out when Val took her quarterly trips back home to Texas to see family.
Jack has a hairy back, so before Val left he sometimes drafted her to help him shave the parts he couldn’t reach. No wonder he dedicates his book to her.
And once his back was smooth and he’d added his blond wig, silicone breastplate, hall of fame wardrobe and detailed makeup, he mustered up all the courage he could to walk out the front door … as Jackie.
Not alone
The other day when we talked he pointed out the scene of the suspected crime I previously mentioned.
“I came through right here,” he said as he pointed to the wooden gate on the side of his house that leads to the backyard. It’s no more than six feet or so from the big, raised porch of the house next door.
That night he had been out in full cross dress mode to a neighborhood bar and was hoping to slip back into the house without any neighbor seeing him.
Unfortunately, Adam, next door, was having a party on his porch.
In panic mode, Jackie tried slipping in through the gate when Adam suddenly called out: “Hello?”
When Jackie didn’t answer, Adam tried again.
Reeling, but still mum, Jackie instead ducked into the garage and finally the house. Soon after the phone rang. It was Adam but Jackie didn’t pick up.
At this point the neighbors thought the Brennan’s house was being robbed and soon the front yard was lit up with police lights and then filled with cops drawing guns.
That led to an unexpected coming out party that left the partygoers gob smacked.
That story – written far better – is how he opens his book.
So, if the title and cover make you pick up Football Sissy, Brennan’s story will keep you from putting it down.
At times, the tale will break your heart. Other times you’ll let out a snort of laughter. And sometimes – like the night he was forced to go to the emergency room after an experiment became a real personal pickle – you’ll just shake your head.
A couple of weeks ago, Football Sissy got a starred review on the selective Booklist website run by the American Library Association.
“They said it was outstanding in its category,” he said proudly.
His book comes at a critical time when the LGTBQ+ community has found itself under siege in the highly-charged political atmosphere that now permeates this nation.
Right wing policies – which Donald Trump embraces even though he is, as someone noted, a Village People superfan – have sought to ban books with gay subjects; scrubbed gender identity from historical reference; pulled funding for HIV prevention and anti-AIDS programs; brokered in destructive stereotypes; and now is planning to cut hotlines helping struggling gay youth.
Brennan said he hopes he can help people have more tolerance and understanding: “I hope people will be a little less knee jerk unsettled by queer people. And I hope it will give people going through this some encouragement and courage and let them know they are not alone.”
These days the 73-year-old Brennan said he isn’t pursuing his CD side as much as he once did.
He and Val – who now have two grandkids – recently took a Scandinavian Tour and found themselves in Finland.
Half of the trip was independent travel, so he said they got a car: “I just felt compelled to go to the Russian border. I had to see just what it looked like.”
He said he didn’t try crossing into forbidden territory and, in fact, admitted: “I really didn’t see anything dramatic.”
Then again, he didn’t need to.
With him, it was a case of been there, done that and he did it in fashion like none of us ever expected.
But like I told him before:
“You’re my pal, heels or no heels.”
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