Buzz Bissinger on His Caitlyn Jenner Story and the Trans Community

The Philly journalist opens up about how he got the assignment, who likes Gucci more, and how they kept the whole thing under wraps.

Philadelphia magazine contributor and author of Friday Night Lights Buzz Bissinger is in the spotlight again this week after penning the much-talked-about profile of Caitlyn Jenner for Vanity Fair. Since the cover hit the web on Monday, he says he’s received hundreds of interview requests. He’s done the morning-show circuit, and appeared on Anderson Cooper and Katie Couric to talk about his experience profiling the most famous transgender woman in the world.

I caught up with Buzz on the phone this morning to find out how the story came about. Why did he get the assignment? What precautions did he take to keep it under wraps? Did he, a man who’s written about his own gender experimentation, glean any insight from his time with Caitlyn? 

How does it feel now that the piece is out and everyone is talking about it?
It’s funny: The actual article is not on stands yet — it’s not due out till later this week or maybe next week — so everybody’s talking about [the cover] without having read the story. I think there’s a really good opportunity here … I believe that Caitlyn Jenner is on the precipice of being able to do a tremendous amount of good and really achieve social change depending on which direction she ultimately takes. I just hope people read it.

How did the story come about?
It started about a year ago. [Vanity Fair editor] Graydon Carter was at a story meeting and said, “Look, we all know there are rumors about Bruce Jenner and indications of a transition going on. Let’s try to see if he will open up.” We reached out to Bruce and he wasn’t ready. But the lines of communication were open. So in January, when he decided that he was going to transition, he reached back out to the magazine and said, “Look, if you want to do this, and do it the right way and do a real story, then I’m ready to do it.”

Why were you chosen to tell it?
The magazine chose me because of the obvious sports connection between Jenner and myself, having written Friday Night Lights. And there was the connection … I’ve cross-dressed in the past. I’ve written about it. I’ve written about gender issues. I’ve written about gender confusion. I know firsthand the difficulty of publicly saying you’re different from the mainstream. That gave us a real common ground to talk about issues like that. I think it made Caitlyn trust me.

How did your connection to cross-dressing come to play in the interview?
We talked about our mutual fondness for women’s clothing. My attraction to it is different from hers. I wear women’s clothes, because it makes me feel sexual; I get a sexual turn on from it. That’s not why she wears women’s clothing. She wears women’s clothing because she was born a woman. It has nothing to do with sexuality. We talked about clothing, we talked about gender confusion, we talked about what it’s like when you’re different and what it’s like to go public with those secrets. It really did give us a mutual sense of what each of us was going through. I want to emphasize that what she was going through was 100 times more powerful that what I had been through. But at least we had a common ground.

Does she like Gucci as much as you do
Yeah, she likes Gucci. I kept saying, “Look, I’ve got a lot of stuff on eBay if you want to buy it,” but I don’t think it’ll fit. She’s a little bit taller than I am. She’s not nearly as much into leather as I am. Leather is my thing. She would kind of tease me about it, and say, “Jesus, wear some synthetic cotton, this is getting ridiculous.”

What precautions did you have to take to keep the interview secret?
Normally when you write a story it’s in a computer system, but this was written off the system. Everything was pretty much done by hand and FedEX. It was like the Dark Ages of journalism. We didn’t want anything in the Vanity Fair system, because we were concerned about leaks. We made corrections by hand. That was the level of precaution: no email, certainly no Vanity Fair/Conde Nast email. Everything off the grid.

Have you gotten feedback from the transgender community since the article came out? 
I saw some person write something that was very dismissive of the piece, and I thought his or her piece was ridiculous and ludicrous. It talked about this idea that [Caitlyn and Bruce] are the same person, and it’s simply not true. The whole point of the piece is that, because of our society, and because of the age she lived in and the stereotypes we have of the male Olympic athlete, she could never live as Caitlyn. It wasn’t possible. She had to live as Bruce. That’s the point. She could never live as herself. So don’t give me this mumbo jumbo that I’ve been ignorant of the issues and that I’ve been insensitive. That infuriates me. … I handled Caitlyn’s story with as much delicacy as I possibly could within the context of this being a real world. And the real world means that Bruce Jenner won the Olympics, not Caitlyn Jenner. And when you’re writing a story like this, it’s very hard. You cannot use the “she” pronoun throughout. I have an obligation to readers — not just the transgender community.

Other than that I’ve heard very little from the transgender community — and they’re an important voice in this thing. I think what Caitlyn has done is great. Listen, I’m aware that Caitlyn is very rarefied. She’s a celebrity, she has money, she has exposure. Most transgender men and women don’t have any of that. They live very hard lives: lives of fear, lives of discrimination, lives of thinking about suicide, and I’m very in tune with that.  

Caitlyn is a celebrity, a reality star, and sometimes it seems like her responses come across rather scripted. Was it hard to get genuine responses from her?
No, actually it wasn’t. Caitlyn is extremely honest, very open and it did not take long to get to that openness.

What was your most surprising takeaway from your time with her? 
It wasn’t like there was a huge “Aha” moment. What I came away with was understanding how painful — physically and figuratively — her life had been as Bruce. How difficult it is to carry a secret, to lie, to live a life of complete inauthenticity. What comes along with that is great shame, and great feelings of deceit and pain. The quote that popped the most to me was … she had her beard removed in the mid- to late-1980s with electrolysis, which is extremely painful and extremely laborious. It’s a two-year process. I asked if she took pain killers, and she said “No, I did it without anything … I felt I deserved the pain, because of who I was.” That really floored me.

That’s when I also knew that this was not some publicity stunt. Yea, she’s going to make money out of it. I hope she makes tens of millions — certainly as much as Hillary Clinton made off that shitty book she wrote. This is not some stunt. That’s ridiculous. 

Can you share any anecdotes that didn’t make it in the article?
In the story, I make it well known that Bruce Jenner as Bruce was unbelievably cheap. The first week I met with him as Bruce, he was moving from his rental home in Malibu to the house he’d purchased in Malibu. He was so cheap he wouldn’t hire professional movers to do it. So it was two day-laborers, his kids, a bunch of his kids’ friends and me. I’m 60 years old and 5-foot-6, for fuck’s sake. I can barely lift a pen much less chairs, but I helped him move and carry mattresses. I said, “This is ridiculous, you should be paying me for this story!” But he didn’t want to spend the money, so it was this bizarre caravan of trucks and minivans tooling down the Pacific Coast Highway.

The issue hits stands June 9th, but you can download it at