Whatever James wants, James gets – and that includes bringing 'The Sun' out for the Tories

Michael Wolff on why Rupert Murdoch turned against Brown

The truth is, Rupert Murdoch really adores Gordon Brown, despite The Sun's endorsement of David Cameron. There may not be another politician in Rupert's nearly 60 years of helping to shoehorn the leaders of three countries into office who has personally appealed to him as much as Gordon. Rupert's voice changes when he talks about him. He gets ruminative (and Murdoch is not a ruminative man), and sentimental, and almost glassy-eyed.

This is in spite of the fact that there is much they disagree about, not least of all Europe. But when it comes to Gordon, political positions are beside the point. It's temperament and heart that are important. Rupert believes Gordon, is all the things a proper man should be: serious, unaffected, unpretentious, down to earth, direct, square (really square). Even his dubious qualities – his remoteness, dullness, frequent inarticulateness and indecisiveness – are, for Rupert, signs of Gordon Brown's good value.

This is partly atavistic. In the same way that Rupert reflexively prefers Australians over everybody else – trusts them more, enjoys them more and can push them around more – he'll eagerly take a Scotsman over any other kind of Brit. He's moved by dour Presbyterians because so many of his own relatives have been similarly dour and Presbyterian. Gordon Brown seems like family to him.

Tony Blair had the advantage with Murdoch of the Scotsman thing too. But Murdoch, while appreciating Blair's attentions, and swayed by his wife Wendi's enthusiasm for Tony, has never really seen him as a kinsman. He admires Blair for his acumen and trickiness, but is wary, too – Murdoch wouldn't want to turn his back with Tony around. Whereas he seems to trust Gordon absolutely. "He keeps his word," Murdoch said during one of our discussions when I suggested that Brown might be, to say the least, inept.

It's not happenstance that one of Wendi's dearest friends is Sarah Brown: Wendi's friends form a Kremlinology of Rupert's alliances and affections.

The truth is that Rupert can't stand David Cameron. He physically reacts to his name. He gets a sour face. His shoulders twist away. The way David looks annoys him: "He's too sharp." The way he talks bothers him: "It's happy talk." His entire mettle as a man, Rupert doubts: "I don't take him seriously. Who would?" And he doesn't trust his politics: "He'll say anything." There's only one mitigating factor in his view of David Cameron: "James quite likes him."

And there's the rub. While he might, in any event, have looked at the prospective fortunes of his friend Gordon Brown, and held his nose and gone for the Tories (Murdoch, who dislikes backing losers, did back John McCain in the US presidential election and is still kicking himself), The Sun's early and critical endorsement of Cameron, cruelly coming as Brown was gamely trying to rally his own troops, is all about Murdoch's son James.

Father and son, Rupert and James, are doing a little dance. The father is proudly trying to accommodate the son; the son is testing the father (and pressing his advantage).

It's a test that has been unfolding for some time: will Rupert let James run his own show? This particular part of the ongoing test – the Cameron part – began not so much with James, who is by nature ambivalent and sceptical about all politicians, but with Rebekah Wade (now Brooks after her marriage, celebrated grandly by the Murdochs, to playboy Charlie Brooks), The Sun's former editor, now the head of News International, best friend of Murdoch's daughter Elisabeth and son-in-law, Matthew Freud, and James's closest personal and business confidante.

Rebekah has been pressing Cameron on James for more than two years. Having brought James over, James and Rebekah together have been pressing Rupert – somewhat to his irritation, but also to his bemusement. He knows Wade is always working him ("she plays my family"), but he likes her game. What's more, to be pressured by James, to be hectored by him, is pure pleasure for Rupert. He bursts with pride. There is almost nothing that James says that he doesn't think is absolutely brilliant.

Still, he really didn't want to forsake Gordon. Even as Gordon was screwing everything up, Rupert seemed to want to hang in there. "Give him a chance, he's smart. Very smart," Rupert said to me during one of Brown's early difficult moments. Equally, he didn't want to give in to Rebekah and James so easily. He liked their campaign. He likes to be courted. Although, each time Rebekah and James arranged for Rupert to be with David, Rupert would, for days after, mutter pointed disparagements about Cameron and the Tories.

When I interviewed Rebekah in the summer of 2008, she queried me closely about what Rupert thought of David. I told her I had yet to hear a positive word. And yet, more than a year ago, he was saying, ruefully, regretfully and begrudgingly, that News International would probably go for Cameron. "It will be James's decision," he said. "It's got to be," he added, as though to convince himself.

He was also coming to another realisation. He was less and less interested in British politics. He had already all but written off Australia politics, could no longer keep the issues and players straight. Now he was finding it harder to keep up with what was going on in the UK. During the London mayoral race, I had to explain to Rupert exactly who Boris Johnson was.

For Rupert Murdoch Gordon Brown represents, I believe, a kind of holding on. Brown is the true conservative candidate for Murdoch, representing the verities of the past. It pained him that James had so brutally timed The Sun's endorsement to embarrass Gordon – but the determination and bloodlessness of the move made Murdoch proud, too. The decision to support David Cameron, with all his modern slickness and frou-frou-ness, is Rupert Murdoch letting go.

Michael Wolff's The Man Who Owns the News: Inside the Secret World of Rupert Murdoch is published by Bodley Head