George Osborne: from the Bullingdon club to the heart of government

When George Osborne was 17, he took part in a school debate on nuclear disarmament. He was then an A-level politics student at St Paul's in London, one of England's leading public schools. On the day of the debate, a crowd of sixth-formers gathered to listen. Osborne, already perhaps displaying latent right-wing sympathies, was to argue in favour of the nuclear deterrent. On the opposing side, his classmate Sam Bain would put the case for the CND. But as Osborne rose to speak, a rugby teacher came into the classroom to say he was required to play in a match. Osborne rushed out, leaving the notes of his speech behind. "Some guy in the audience read it out and he won pretty unanimously," recalls Bain now. "So basically, I failed to win a debate against him even though he wasn't there."

For Bain the humiliation was not entirely unexpected. Even as an adolescent, Osborne seemed preternaturally composed, somehow older than his contemporaries and with a clear idea of where he was heading and of the kind of person he wanted to become.

"We were 17, and at that point he was grown-up in a way that no one else was in our year," recalls Bain, who went on to co-create Channel 4's Peep Show and the new student comedy Fresh Meat. "He looked and behaved like a man who had already decided what he was going to do with his life."

The story of how that teenager went on to become the youngest chancellor of the exchequer in 120 years is an intriguing one. It contains many surprising elements, including tales of riotous debauchery, allegations of electoral malpractice in student politics and, at one point, an intimate encounter with the pop star Geri Halliwell – more of which later. But in many ways Osborne at 40 still retains the essence of Osborne at 17. Those who work for him now remark on his exceptional political brain, on his ability to outthink his opponents with strokes of tactical genius, to present even the most dense economic argument with an eye to what will make the next day's headlines and to know, deep down in his bones, what will win over a crowd.

"I remember many times when we were faced with a tricky political problem and there'd be a lightbulb moment," says Conservative MP Matthew Hancock, who was Osborne's economic adviser and chief of staff until last year. "There's nobody else I've ever met where that moment was so obvious – his entire face would light up and he'd say: 'No, we'll do it like this.' And it was always a really brilliant idea. He's very creative."

Yet for all that he inspires loyalty among those who work for him, Osborne has enough self-knowledge to realise that his public persona is fatally lacking. On television he comes across as stilted, lacking David Cameron's easy bonhomie and banter. In parliament his youthful features – a plump, pale face; foppish dark hair – only serve to underline the impression that he is an overgrown public schoolboy not quite up to the job of steering the country through a devastating financial crisis. His privileged upbringing – Osborne is the eldest son of Sir Peter Osborne, the 17th holder of a hereditary baronetcy and the co-founder of wallpaper designers Osborne & Little – adds to the tabloid caricature of a toff with a trust fund. His mouth, according to one commentator, "is curled into a permanent sneer so it looks as if he's laughing when he announces yet more cuts to public services".

Unhelpfully, he is forever dogged by two infamous photographs from his past: the first, taken in 1992, depicts Osborne as a latter-day Sebastian Flyte, resplendent in tails and a blue bow tie as a member of Oxford University's Bullingdon Club; the second, taken a few years later, shows him grinning inanely with his arm flung casually around the shoulders of escort Natalie Rowe, surrounded by empty bottles of wine and what might or might not be a line of cocaine on the table in front of him. Those two images have reinforced – unfairly or otherwise – an overriding public sense of Osborne as a dilettante possessed of a healthy sense of entitlement. At a time when he is championing a series of swingeing austerity measures, Osborne is only too aware that such a preconception is unfortunate.

As a consequence he carefully rations his public appearances – a tactic that has earned him the nickname of "the submarine" among Tory staffers. "He stays underwater for a long time and when he appears he prepares impeccably," explains Janan Ganesh, the political correspondent for the Economist who is currently writing a biography of Osborne. "He's very open in private that he will – in his words – 'never be a man of the people'. It's a combination of material privilege and more superficial stuff, like the way he looks and sounds… During the past election campaign, for instance, he was not visible. That was because he knew he was more of an asset behind the scenes."

Osborne at 17 could win a school debate without having to appear in person, but simply by having someone else read out his cleverly structured arguments. Twenty-three years later, as chancellor of the exchequer, that same strategy has been successfully refined and redeployed, albeit on a rather larger scale.

For Sam Bain, Osborne's erstwhile debating partner, there is a feeling of inevitability about his classmate's rise to power. "I certainly feel very old now looking at him as chancellor, but thinking about how he got there, it does make sense," he says. "You probably have to be working at it for 20 years or more to achieve that. It does speak of someone who is very single-minded, and whether or not you agree with his politics, that's a pretty extraordinary thing."