James Middleton: Kate’s Bad-Boy Brother

He’s been photographed half-naked, mooning the camera, and dressed in drag. Tom Sykes on why Kate Middleton’s little brother has the palace wringing their hands

He’s been photographed half-naked, mooning the camera, and dressed in drag. Tom Sykes on why Kate Middleton’s little brother has the palace wringing their hands. Plus, see photos.

Just when the newlywed royals thought Osama bin Laden had knocked them off the front page for good, up pop a set of photographs of young James Middleton—Kate’s handsome 23-year-old little brother, who read the lesson in Westminster Abbey last week—engaging in all sorts of embarrassing activity, including dressing up in a French maid’s uniform and flashing his buttocks with a group of male friends next to a rural road sign reading “Back Lane.”

Rumors have long circulated that James is gay—if you type “Is James Mi” into Google, it fills in “ddleton gay” for you—spurred on by the triple whammy that he a) runs a cake-making business, b) is devastatingly handsome and is therefore an object of gay wishful thinking, and c) didn’t take a guest (male or female) to the wedding. The world’s media has jumped on the latest pictures to continue their drawn-out game of nudge-nudge wink-wink, finding ways to suggest James is gay, without, of course, actually saying so. Fleshbot couldn’t resist inviting us to meet “the man who would be Queen.” British newspapers including The Telegraph and The Daily Mail have a history of referring to him as “flamboyant,” a traditional British code word for gay.

The pictures of James indulging in a bit of mooning should be taken in the context of the upper-class British tradition of homoerotic, public-schoolboy clowning.

In fact, James’ sexuality is a mystery. One well-placed insider says, “I don’t know whether James is gay or not. The rumors have been fueled by the fact that although he is constantly surrounded by beautiful women, he has never been in a long-term relationship. It may well just be that he hasn’t found the right woman yet.”

The latest pictures of James posing nearly naked by a fire and indulging in a bit of mooning should be taken in the context of the upper-class British tradition of homoerotic, public-schoolboy clowning. The truth is that dressing up in drag and pretending to be gay have been part of posh male British horseplay for centuries. A clear line can be drawn from James Middleton’s latest japes to D.H. Lawrence’s depiction of male toffs wrestling naked by the fire in Women in Love and the medieval depictions of penises entering bottoms that adorned the margins of even the most sacred texts—and were read only by educated men.

Most Britons would be much more unimpressed by pictures—published only in Australia because British editors did not want to run the risk of falling foul of the Press Complaints Commission—taken in April 2009 of James urinating on the street following a big night out in London. Gay streaks are fine in British society; loutish tendencies are definitely not.

Like his sisters, James went to school at Marlborough, one of Britain’s most expensive boarding schools, but dropped out of Edinburgh University in 2007 after one year to set up his unusual business, called the Cake Kit Company. “Within a few weeks I knew it wasn’t where I wanted to be,” he told The Daily Telegraph of his university days. “I was always looking for business ideas.”

James said the idea of a business making themed birthday cakes—with the slogan “Home made, made even easier!”—came from an article that said a mother baking is one of the most powerful childhood memories. He developed his birthday-cake packs on themes such as football, dinosaurs, lions, rockets, fairies, and handbags. Each includes the cake mixture, icing, candles, and a disposable baking tray.

Last year The Daily Mail published pictures of James wearing one of his sister’s polka dot dresses to a drag party. Says Katie Nicholl, the Mail on Sunday journalist and author of the book The Making of a Royal Romance: “It’s all part of that public school, dressing up, prankish lifestyle. It is what public-schoolboys do. He was just having a laugh and the last thing he expected was for those pictures to end up in a paper. Those pictures actually did not really bother him. The pictures that did upset him were the ones of him urinating.”

There were some concerns that James was going to be the one to shatter the perfect image of the Middleton family—but in the end that role fell to Kate’s dodgy, drug-distributing Uncle Gary.

Nicholl says James’s mother, Carole, had “a quiet word” with him after the urinating pictures emerged, and asked him to “try and keep a low profile” for the sake of his sister.

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“That was when things changed,” says Nicholl. “James adores Kate, he was determined not to ruin things for her, so he just stopped going out. He loves partying and socializing, but he was clearly prepared to sacrifice that for Kate. And he played his part at the wedding to a tee.”

James is not above bragging about his sister’s romance, however. When he does go out, one of his favorite haunts is the Fulham, London nightclub Maggie’s, themed in homage to right-wing icon Margaret Thatcher. According to one source, he has been spotted in there holding court, saying, “My sister is going to be the future queen. You will all be bowing to me one day.”

The remarks were apparently made with tongue in cheek, but such reports still alarm some at court, certainly much more than a few silly schoolboy pictures ever will. The fact is that the private albums of many royals and British peers probably contain similar pictures. It’s quite normal. James Middleton’s only sin is to live in an age when digital photography and the Internet makes global dissemination of these images so easy.

Tom Sykes, 36, is a British writer and journalist. He was formerly nightlife reporter for the New York Post and now tries to live a largely blameless life in Ireland with his wife, two kids, three pigs, six hens, and a turkey. He is the co-author, with Detmar Blow, of Blow by Blow, a biography of Isabella Blow.