A legendary loser starts his own school.

The British journalist Toby Young is best-known for parlaying a disastrous stint as a writer at Vanity Fair into a best-selling book, How to Lose Friends and Alienate People, which showcased his exceptional talent for doing both. In 1995, Graydon Carter plucked Young from his perch at a failed British cultural journal and installed him as a contributing editor at Vanity Fair. It was Young’s dream job, and so he immediately set about screwing it up. In a year and a half, he was paid around $85,000 and wrote less than 3,000 words, which made him, by his own estimation, the highest-paid writer in the magazine’s history. Before he was eventually shown the door, he devoted most of his energy to self-destructive stunts, such as ordering a strippergram in the office on Take Our Daughters to Work Day. He has been variously described—even by people who like him—as an annoying hack, a celebrity-obsessed opportunist, and a man who personifies failing upward.

His latest venture may therefore appear a bit out of character. In August 2009, Young announced plans to establish a free school in the West London neighborhood of Hammersmith and Fulham, near his home. Free schools—the British equivalent of charter schools—are a new initiative of the Cameron government. Like charters, they will be funded by the state and operate outside local control, an arrangement that proponents say will raise standards, introduce more choice, and eliminate current and future overcrowding. Their detractors—led by Labour MPs and teachers’ unions—protest that they’ll siphon money and middle-class students from existing state schools without improving quality. Hundreds of charity and parent groups have applied to launch their own schools. Yet, of all these applicants, it was Young’s group that won the first funding agreement from the government. The West London Free School is slated to open in September.

I met Young for lunch recently at a sushi restaurant in West London. He is now 47, and, while he is certainly confident, there was no sign of the in-your-face loser of his book. Granted, Young has always cannily exaggerated this shtick for comic effect, but in our conversation he sounded positively wonkish. He earnestly informed me that he now spends 50 to 60 hours a week poring over teacher résumés, funding requirements, and building-site studies. “It has become a crusade, and everything is now riding on this,” he says. “I’ve made a career of failing in the past. That’s over now.” For a man who used to spend the majority of his waking hours devising new ways to get himself mentioned on “Page Six,” this was a transformation bordering on the implausible.

After lunch, Young took me for a walk down leafy King Street, past the large Victorian building that will house his school. The project, he explained, was inspired by what he sees as the dumbing down of the British education system. At state schools, he said, traditional subjects have been abandoned in favor of skill-based vocational courses. Meanwhile, the exceptional private schools that feed students into Cambridge and Oxford remain out of reach for most families. To address this shortcoming, Young plans to offer a rigorous diet of history, science, and mandatory Latin, available to all children regardless of income. “There’s evidence schools with the right ethos and the right curriculum can take children from low-income families ... and achieve extraordinary results,” he says enthusiastically. More than 440 children have applied for the first class’s 120 places; Young says that 3,000 parents have registered for future spots.

In the process, however, Young has managed to become the target of public anger about the entire free-school movement. “You know, I’d led a fairly dissolute life and hadn’t really done much of redeeming social virtue,” he told me. “I then embark on this philanthropic project and I think, ‘I’m going to make some friends now. People are going to respect me.’ And actually I’ve never been more widely disliked or publicly reviled.”

Many have responded to the notion of Toby Young creating a school with open outrage. Over the past few months, Young has been yelled at during public meetings, denounced on television, and called every rude name in the book on Web forums frequented by free-school opponents. In a lengthy rant attacking the project, John Crace, a feature writer for the Guardian, wrote that, “[l]ike his ego, Toby’s ignorance is almost limitless.” To his critics, Young embodies the worst of the free-school project: elitism, an unwillingness to improve existing schools, and an arrogant belief that someone with no experience in education can swoop in and solve the shortcomings of Britain’s education system. As one local parent put it to the BBC, “Who would you rather have setting up your school: your local council, who you at least elect, ... or Toby Young?”

Young’s critics have also snidely pointed out that he has a personal motive for setting up his school: He has four children of his own, all under eight years old. Indeed, Young himself told me that he first toyed with the idea of starting a new school because he was unhappy with the options available to his kids. “There wasn’t anywhere our children could get a classical liberal education unless we paid for it, we got religion, or we were prepared to move,” Young says. “And we thought, ‘Maybe there’s a fourth choice.’” So has Young finally grown up, or has education reform simply replaced the media gossip pages as his self-promotional vehicle of choice? In the end, it may be a bit of both: The tricky thing with Toby Young is that you can never quite tell whether or not he’s for real.

Carolyn O’Hara is a writer based in London. This article originally ran in the April 7, 2011, issue of the magazine.