On Monday, Vanity Fair introduced Caitlyn Jenner, the woman previously known as Bruce, to the world. The magazine posted a cover image of the former Olympic decathlon champion, shot by Annie Leibovitz, that is conventional in its composition but radical given the journey Jenner took to seize the femme fatale role as her own. But perhaps the most interesting thing about Vanity Fair’s story is not Caitlyn’s new name or the way her body now matches her brain, but the person who’s writing the story that will accompany the striking picture: Buzz Bissinger, a writer best known for sports books like “Friday Night Lights,” “Three Nights In August” and “LeBron’s Dream Team.”

I don’t think anyone would have been surprised if Bissinger were reporting on Jenner’s athletic accomplishments, given where the former has focused a lot of his professional energies. But reporting about sports often involves writing about gender and its many expressions. And given Bissinger’s own recent writing about style, sexuality and his own relationship to his sexuality and gender identity, he just might turn out to be a perfect choice to chronicle this stage in Jenner’s story — and to remind us that Jenner’s story is not everyone’s.

“Friday Night Lights” is ostensibly about a season in the life of the Permian Panthers football team, and the role of the team in the culture of Odessa, Texas. But Bissinger’s real subject is the way the masculine ideal that centers on the players themselves both privileges them and sets them up for later difficulties. These ideals are inflected by race: “It was clear that the coaches expected black athletes to be better because of a belief that their bodies matured earlier than did those of whites,” Bissinger writes. Even players who benefit from the adulation of the town sometimes feel more at home somewhere else. Ivory Christian, a talented player, also preaches in his church, and it’s there, rather than on the gridiron that “[h]e truly seemed at peace in these moments, able at last to lose himself in something without anguish and ambivalence.”

Permian football creates gender roles for women, too: Bridgitte, a cheerleader for whom homecoming was the highlight of her life, finds a gap between her ambitions and the tools she has to actualize them. Though she’s not actually qualified to go to college yet, “[s]he wanted to go into the medical field. She wanted to be Miss Universe. She wanted to open a dance studio. She wanted to be famous. She wanted to write a book about her life.”

Eddie Driscoll, one of the top students in Permian’s academic rankings, recognizes that he’s shut out of the ideal. “No matter how many books he read, no matter how exquisite his arguments in government class about gun control or the Sandinistas or the death penalty, he never got the latest scoop on who was having the weekend parties,” Bissinger writes. “Only the football players were privy to that sacred knowledge.” But his short-term jealousy probably sets him up better for his life to come than the adulation that those initiates receive. “We all feel that our husbands have been unhappier with everything after they got out of it,” one woman married to a former Panther tells Bissinger. “You see your name up in lights and people follow you and they put your name in the newspaper and then all of a sudden the season is over. . . .”

“Three Nights In August,” which follows Tony La Russa through the management of a late-season series, follows the process by which one man molds others, though at a higher level of professional sports, and at a later point in the latter group’s lives. Bissinger is interested in La Russa because he believes La Russa cares about “the human ingredients that make a player a player and make a game a game: heart, desire, passion, reactions to pressure.”

Bissinger doesn’t have to say explicitly that he’s writing about men. The subject just comes up again and again, as when he says that “Dave Duncan is the kind of man who in the storm at sea would simply lash himself to the mast; he’d wait out the hurricane by reading the paper, hold the putter steady in the tornado.” At one point, after pitcher Darryl Kile’s death, La Russa reads an excerpt from Kile’s writing about how he coped with his father’s death. “I don’t think I’ll ever get over it, but my father was my best friend,” Kile wrote. “But in order to be a man, you got to separate your personal life from your work life. It may sound cold, but I’ve got work to do. I’ll never forget my father, but I’m sure he’d want me to keep on working and try to do the best I can.” That’s an old-fashioned idea of manhood, but in the context of La Russa’s need to keep his team moving forward despite their loss, it’s a useful one.

And two years ago, Bissinger published a piece in GQ, “My Gucci Addiction,” that I’ve returned to time and time again. The piece is partly about how much money Bissinger spent when he discovered high fashion, finally indulging himself in a curiosity and passion that he’d repressed for most of his life. The cost of self-actualization, at least the moment of transcendence Bissinger achieved on the night that ends the piece, he prices out at $638,412.97. But while the money is a gaudy distraction, “My Gucci Addiction” is really about Bissinger’s attempts to fashion a sexual and gender identity for himself through fashion. The measured critic of the rigid hypermasculinity of Permian, or the observer of the stoic ideas of Tony La Russa’s clubhouse finally stepped forward to present himself as an example of binary-busting experimentation who, like Jenner, has the money to try to become exactly who he wants to be.

“Gucci men’s clothing best represents who I want to be and have become — rocker, edgy, tight, bad boy, hip, stylish, flamboyant, unafraid, raging against the conformity that submerges us into boredom and blandness and the sexless saggy sackcloths that most men walk around in like zombies without the cinematic excitement of engorging flesh,” Bissinger wrote in the piece. “Some of the clothing is men’s. Some is women’s. I make no distinction. Men’s fashion is catching up, with high-end retailers such as Gucci and Burberry and Versace finally honoring us. But women’s fashion is still infinitely more interesting and has an unfair monopoly on feeling sexy, and if the clothing you wear makes you feel the way you want to feel, liberated and alive, then f—— wear it.”

As an Olympian, Caitlyn Jenner was an avatar of male physical perfection. As a Vanity Fair cover model, she’s embraced a hyper-feminine ideal. Bissinger acknowledges in “My Gucci Addiction” that he doesn’t find a resting place that is quite so easily understandable: His desires make him stand out, rather than letting him disappear into a pre-approved expression of gender identity. “I never fit the traditional definition of a sexy male straight or gay—tall, ripped, six- packs within six-packs,” Bissinger writes. He likes playing with makeup and wearing high heels, but as a man, not as a woman.

If Caitlyn Jenner is going to embody one way of being transgender, transitioning physically and trying, as much as possible, to look like society expects, Bissinger brings a different, and in some ways more challenging perspective to the story of gender identity in the twenty-first century. Caitlyn Jenner’s journey may make it easier for people who see themselves in gender archetypes that already exists. Bissinger’s experience reminds us that those ways of being a man or woman aren’t enough for everyone.