When Peter Oborne bought a hare-coursing dog to compete in the last Waterloo Cup, it died before the race. But when he bet on the length of the Budget speech, he outwitted the bookies and made a killing. Given that Oborne is one of the major backers of David Cameron in the press, Conservatives heading for Bournemouth today will be hoping that in politics at least, his gambler's instincts are correct.
Oborne, 49, formerly political editor of The Spectator, and before that a writer on the Evening Standard and the Sunday Express, joined the Cameron camp after initially backing Kenneth Clarke in the leadership race. Now, newly contracted to the Daily Mail for a reported £200,000-plus, he is one of the Tory leader's biggest fans, yet he cannot be counted on for slavish devotion. "He's no party apparatchik," says one who has worked with him. "He will always go with the story rather than be a foot-soldier for a loyal cause."
Oborne, whose first Mail column appeared on the eve of the Labour conference, is predicting a low-key gathering on the south coast. "Last week was such a horror story with New Labour riven by fratricidal vendettas and the spectacle of the party of government ripping its soul out, that the Tory conference is inevitably going to be quieter.
"You can, however, see an attempt by right-wing columnists to force Cameron down the route taken by all recent Conservative leaders, focusing on immigration and lower tax. That definitely has a real attraction to voters and it could be a problem for Cameron."
The relationship between politicians and the press is a subject close to Oborne's heart. Though in many ways he fits the stereotype of an old-style Tory - he belongs to the Beefsteak Club, sends his son to Winchester and writes a column for The Sportsman under the alias Colonel Pinstripe - yet he is seen as a somewhat anarchic figure by his journalistic colleagues.
His big theme is the hypocrisy and mendacity that arise where the media and politics meet. In books such asThe Rise of Political Lying and his biography of Alastair Campbell he has probed the growth of political spin and the evasions that politicians employ in their dealings with the press.
One was the story of Tony Blair's attempts to secure a bigger role at the Queen Mother's funeral, which Oborne broke while at The Spectator.
The relationship of journalists with each other, however, has earned him more salacious coverage.
At the 2002 Labour conference, senior politicians were treated to an entertaining spat between Oborne and Andrew Marr, then the BBC's political editor, after Oborne accused him of being "squalid, false and immoral" in suggesting John Major emerged a more interesting person from his affair with Edwina Currie.
Striding across the breakfast room, Marr shouted: "You are a shit, a sanctimonious shit. You'll do anything for money. That's what I think of you and I just wanted you to know that." Oborne later retaliated with a piece about Marr being thrown in a pond as an undergraduate.
Oborne hopes the Cameron leadership heralds a new era in relations between media and politics. "One of the most attractive things about Cameron is that there's no enforcer. There's the press officer, George Eustace, but he's not a political thug. It's refreshing because Alastair Campbell was so destructive of integrity in politics. The Conservatives do have a tight inner core and Steve Hilton is incredibly important, but as a Philip Gould figure, a strategist, rather than a Campbell."
New Labour, he maintains, became damagingly obsessed with the media. "Blair would have a tailored strategy for every journalist. New Labour were paranoid about the media classes and that was part of their method of getting into power. But that obsession is also why Blair has failed. Senior Conservatives like Oliver Letwin, one of the most attractive figures in British politics, are getting on with policy. The energy in the Cameron camp is not media driven."
While The Independent's Bruce Anderson led the way in supporting Cameron, joined by Danny Finkelstein of The Times, The Spectator's Matt D'Ancona and The Daily Telegraph's Alice Thomson, among the rest of the British press, support is divided. The Daily Mail, which Oborne describes as "pretty friendly" to Cameron, has also nursed a close relationship with Gordon Brown. And on the Conservative's ancestral house journal, The Daily Telegraph, Simon Heffer has maintained a vitriolically anti-Cameron line.
"The Telegraph seems to have taken the decision to disengage from mainstream politics," says Oborne. "It is fundamentally anti-Cameron even though the Telegraph is historically by far the most important Conservative paper."
He has been at pains to convert one of his closest friends, Jeff Randall, the Telegraph's editor-at-large, but to no avail.
"I've said to Jeff his reaction to Cameron is extremely primitive and Neolithic, but he won't accept it and feels Cameron is betraying something."
Perhaps the single biggest question mark concerning Cameron and the British media is his relationship with the Murdoch press. So far Rupert Murdoch has equivocated: from pronouncing Cameron "charming" but lacking in substance, to suggesting he could foresee supporting the Tories in the next election.
But Oborne questions whether Murdoch's backing is crucial. "Cameron obviously models himself on Blair and might have been expected to suck up to Murdoch, and I'm impressed he's refused to do that. A benign interpretation of that stand-off is that Cameron is a man of principle."
He is, anyway, dismissive of the whole idea of a Conservative press. "The Tory press is a fantasy in the minds of people like Polly Toynbee. It doesn't exist any more and it hasn't since 1990 when it fragmented and parts of it then went pro-Blair. The real division in the British press is between the neocons and the rest - America versus Europe if you like - and in the neocon camp I would put the Telegraph, News International, the Express and The Observer [because of its stance on Iraq and Blair's foreign policy]."
His next project is not Cameron, but Gordon Brown, the latest in a series of TV documentaries for Channel 4. He is also writing a book, provisionally entitled The Triumph of the Political Classes, in which he traces a view that certain groups in society, such as churches and voluntary associations, are unnecessarily being brought under the umbrella of the state.
"He does hold very strong views and is not afraid to put them," says his friend, Piers Pottinger, who has been writing Colonel Pinstripe with him for 20 years. "He gets these great enthusiasms which mean he gets carried away from time to time. He is very much his own man."
How the other conservative pundits line up
Bruce Anderson The Independent
The staunchest of Cameroonians, he spotted Dave years ago and remains lost in admiration
Matthew d'Ancona The Spectator
A former Portillista, he riled Lady Thatcher so much she supported Iain Duncan Smith for leader. In Dave's tent
Alice Thomson The Daily Telegraph
She and her husband, Edward Heathcoat Amory, are loyal members of the 'Notting Hill set'
Simon Heffer The Daily Telegraph
Thatcherite. No fan of Cameron
Daniel Finkelstein The Times
An adviser to William Hague and John Major. Is seen as a policy wonk
Much wringing of hands at The Guardian last week over whether Cherie Blair's alleged remark about Gordon Brown being a liar was real news. Political editor Patrick Wintour thought so and was writing it up with gusto when his predecessor, Michael White, looked over Wintour's shoulder, saw the words on his screen, and sharply told him it was "not a story". White was ignored.
Whose lime is it?
Graham Norton has been crossing swords with the Evening Standard about a lime tree near his house that the paper claimed he wanted cut down. Some weeks ago, he wrote to editor Veronica Wadley explaining that "the entire story is a work of fiction". Oh dear. "Happily," wrote Norton "since you are a quality paper, you managed to include two facts. I live in Wapping and someone has made a planning application to chop down a lime tree." He then complains of being quoted as having called the tree "an eyesore". "Who... would refer to any tree in this way? Didn't your crack team of investigative journalists find out that I'm a financial supporter of Trees for Cities? The bottom line is that there is no dispute about this tree and if there is, I have nothing to do with it. My only argument is with lazy, stupid journalists who insult their readers with this sort of dreary rubbish. No wonder your price is going up to 50p if you have to pay two people to read a free local paper and reproduce every fictitious word of it. Tree lover and fact fan Graham Norton." Sportingly, the Standard replied, apologising for "any embarrassment this may have caused".
Missing a beat
The Today Programme on Radio 4 on Friday gave not just a backslap but a back rub to its BBC neighbour Radio 3, currently celebrating its 60th birthday. Radio 3 controller Roger Wright told Today that listening figures had dipped below two million, but this was just a seasonal fluctuation. So the figures, and recent changes to "broaden" (dumb down?) the station's appeal, have nothing to do with the existence of Classic FM? Evidently not in the opinion of interviewer Ed Stourton, who failed to mention the commercial station. We're told Questions on Classic FM were discussed by the Today team, but weren't asked.
Deborah Summers of the Glasgow Herald has been made Guardian Online's new political editor. Summers, known affectionately as "Dim Debbie", is not held to be the quickest greyhound out of the traps. Legend has is that once, on seeing an Independent front page about Niger, she rushed around the office saying: "How could they use that word?"
Odone's done for
Two of the The Guardian's most distinctive media voices are moving on. Cristina Odone and Kim Fletcher, who alternate as columnists in the Monday supplement, are off. Fletcher, formerly of the Telegraph group, will stay until December, but Odone has cut her ties immediately. "They said they wanted a single voice and that they have been courting this one person for a while," says Odone. "I don't know who it is." Media editor Matt Wells won't say, but don't rule out Peter Wilby.
What goes around comes around. When the history of The Daily Telegraph is written, its authors should pay heed to an unfavourable book review written in May by Washington bureau chief Alec Russell. The subject was a volume on Tony Blair's relationship with the US by Con Coughlin, then (merely) the Telegraph's security correspondent. And who was it who wielded the axe on Russell and the rest of the paper's US operation the other day? None other than "Genghis" Con Coughlin, now executive foreign editor. Nothing personal, of course.