Rupert Murdoch, the Establishment and why I can't wait to see Conrad Black on Have I Got News for You

On outsiders pretending to be insiders and insiders pretending to be outsiders

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This evening Conrad Black, the disgraced crook and former media proprietor, will appear on Have I Got News For You. If you've seen his rumpus with Jeremy Paxman on Newsnight earlier this week, or with Adam Boulton a day later, you'll know that we've reason to expect fireworks. I'm obviously rooting for Ian Hislop to give him a hard time, and suspect he will.

I hadn't realised until this week just what an astonishing creature Black, who I have never met, is; and in particular, the effort he has invested in earning the affection of the British Establishment. A brilliant, maverick and ultimately criminal businessman, the latter half of his career seems to have been devoted to a form of wealthy entryism.

He bought the Telegraph titles, morning bibles of the aristocracy. He got the townhouse in Kensington. He hosted lavish parties, and most devotional of all, in 2001 he renounced his Canadian citizenship in order to become a member of our House of Lords.

In all this, he was in direct contrast to his great rival, the brilliant Australian-American Rupert Murdoch. Sure, Murdoch got cosy with Britain's rulers – but only because he abided by the principle that you keep your friends close but your enemies closer. He bought the Sun and News of the World, morning bibles of our working-class. Sure, he bought the Times' titles, but he immediately declared his aim to purge them of servility. He based himself in New York, not Kensington. He didn't so much host parties as let his children host them for him.

Murdoch's career in Britain is best understood as a decades-long insurrection against the Establishment. He's a republican who thinks we're ruled by amateurs and lefties – and sometimes a combination of the two – exemplified by the BBC. Murdoch's career in Britain was a project aimed at shaking the very foundations of Britain and changing it from below. Black's career in Britain was – still is – a project aimed at lubricating the upper echelons of our society, and so keeping it the same. The Australian is an outsider pretending to be an insider, whereas the Canadian is an insider pretending to be an outsider. Rupert the Radical, the great debaser; and Conrad the Courtier, the great debaucher.

This is the context in which to see and understand the latter's prolific media spree. The irony is that Black's so desperate to be loved by our Establishment he's going around television studios threatening to punch some of the nation's favourite journalists.

I can't wait for tonight!