Shortly after I started working at Vanity Fair in the mid-1990s, I suggested to my boss Graydon Carter that I write an article about the number of New York society types who were bankrupt. Not morally bankrupt, but up to their eyeballs in debt. ‘Let’s get a team of researchers to go through the financials of everyone on the guest list of the annual costume ball at the Met,’ I suggested. ‘We could publish a list, like the Forbes 400, but the exact opposite: America’s most indebted billionaires.’

Graydon didn’t go for it, and not just because he was worried about its impact on his social life. ‘Like who?’ he said. I rattled off a list of names, but he pooh-poohed every one. ‘This is just wishful thinking, Toby,’ he said. ‘The truth is, they are all rich. Much richer than you or I will ever be.’

There have been numerous occasions since when I wished I’d stuck to my guns. Turns out, I was right and Graydon was wrong and we wouldn’t have had to search very far to find examples of the phenomenon I was talking about. In 2004 it emerged that Annie Leibovitz, Vanity Fair’s in-house photographer, was underwater to the tune of $24 million. I daresay half the staff were flat broke, desperately trying to keep up appearances while their creditors circled.

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L’Wren Scott, Mick Jagger’s girl-friend, is a case in point. After she committed suicide last week, it emerged that her fashion business was £6 million in debt. Not that you would have known it to hear her talk. ‘I always say luxury is a state of mind,’ she told the Sunday Times last November. ‘Because for me, it really is. It’s legroom, it’s a beautiful view, it’s great food at a great restaurant you’ve discovered because you obsessively read Zagat, as I do.’

People have wondered why she didn’t reach out for help, or simply let her business go under and relaunch herself on a more modest scale, but New York isn’t that sort of place. Once a person has ‘arrived’, once they’re a ‘bold-faced name’, they feel they cannot admit to any setback without jeopardising their A-list status. Everything becomes subordinate to the need to maintain that reputation, including their personal happiness. L’Wren Scott’s suicide wasn’t a case of death before dishonour, exactly. More like death before disrespect.

There’s something peculiarly American about this attitude and it’s connected with the absence of a class system — or, more precisely, with the fluidity of America’s class system. In America, people are judged by where they’ve ended up, whereas in Britain it’s more about where you start. That means that someone can go bankrupt in London without it making much of a dent in their self-esteem, particularly if they’re from a privileged background. Their social status, and by extension their self-worth, is more closely connected with whether they speak with the right accent than it is with their income. There’s more shame in saying ‘toilet’ than there is in personal debt.

Take the case of Tina Brown, a New Yorker whose business ventures have lost far more than L’Wren Scott’s ever did, but who is completely inured to these setbacks because of her posh English upbringing. According to a profile of her in the current issue of GQ, Brown’s latest venture, the Daily Beast, lost $100 million in the five years that she was at the helm. That’s on top of the $54 million lost by her previous venture, Talk magazine. If you factor in the tens of millions of dollars that Vanity Fair and the New Yorker haemorrhaged under her stewardship, not to mention some of her other failed ventures — like her talk show for CNBC — I would conservatively estimate she’s lost her backers a quarter of a billion dollars.

But is she bothered? Is she hell. You won’t find Tina retiring to a darkened room with a bottle of whiskey and a revolver. On the contrary, she’s just signed a contract with Doubleday to write her memoirs — the appropriately titled Media Beast. Failure is just another career opportunity for her, which has always been the British way. As Winston Churchill said, ‘Success is going from one failure to the next with no loss of enthusiasm.’

I’m not sure which is worse — the hypersensitivity of up-by-their–bootstraps Americans or the unimpregnable self-regard of born-to-the-purple Brits. Is there a balance to be struck between the two? I don’t want Tina Brown to top herself, but it would be nice if she was just a teensy weensy bit deflated by the sheer scale of her magazines’ losses.

Toby Young is associate editor of The Spectator.

This article first appeared in the print edition of The Spectator magazine, dated

Tags: Daily Beast, failure, GQ, Graydon Carter, L’Wren Scott, Met ball, New York, New Yorker magazine, prominent bankrupts, Society, success, Tina Brown, Vanity Fair, Winston Churchill