In late 2014, Graydon Carter, then the editor of Vanity Fair, was meeting with features editor Jane Sarkin and had a thought, although the kind of thought one usually keeps to oneself. (Carter is also the founder and a co-editor of AIR MAIL.)

It had been reported over the years in the tabloids that Bruce Jenner, the gold-­medal-winning Olympian and late-­70s icon, was secretly a cross-dresser. To a new generation, Jenner was the sad-­sack husband of Kris Jenner, father to Kendall and Kylie, stepfather to Kim, Kourtney, and Khloé, patriarch and bit player on Keeping Up with the Kardashians.