In his heyday, Lord Black of Crossharbour strutted the world stage as press baron, confidant of statesmen and biographer of American presidents.

The Canadian-born peer, as head of a global newspaper empire that included the Telegraph titles and Spectator magazine, held London in his thrall with parties for journalists, academics and politicians at his double-fronted house in Cottesmore Gardens, Kensington, with Barbara Amiel, his glamorous columnist-wife.

Yesterday the self-regarding former Telegraph chairman, who once famously dressed up as Cardinal Richelieu for a costume party at Kensington Palace (with his wife on his arm as Marie Antoinette), confronted the humiliating prospect of donning an orange prison jumpsuit instead.

“He wanted to be the hero, but for some reason he has always wanted to be the dying hero. He has this very melancholy view,” said George Tombs, the author of a new Canadian biography entitled Robber Baron: Lord Black of Crossharbour.

The romantic hero who has run out of plots

Conrad Black, who once dressed up as Cardinal Richelieu, faces the prospect of donning an orange prison jumpsuit instead

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“He has always tried to portray himself as a grandiose, dramatic figure, but very ofen these comparisons have been to people who lost out,” Mr Tombs said. “Having seen him at the trial, the only Shakespearean character I can compare him to is Richard III, the hunchbacked Machiavellian who has betrayed everyone and was betrayed himself at the end. All he can do is cry desperately, ‘A horse! A horse! My kingdom for a horse!’ ”

Lord Black himself bristles at suggestions that his spectacular downfall was provoked by a fatal flaw in his character.

While awaiting sentencing on $21 million (£10 million) bail, he unleashed his cannon on Peter Newman, the veteran Canadian journalist, for writing that the peer’s highfalutin language was merely a mask for “seismic insecurity”.

“A historian as learned as Black ought to have realised that empires fall more quickly than they rise, and almost always because of the fallibility of their leaders,” Mr Newman, Black’s first biographer, wrote in Toronto Life magazine. “No one lived out that cycle more tragically than Black’s role model, Napoleon Bonaparte, who turned a Belgian village named Waterloo into the metaphor for an epic military defeat and the end of his presence on the world stage. That will likely also be Black’s fate.”

Black peremptorily dismisses such colourful explanations for his troubles. “This theory that it’s all a great ‘rise and fall’ story or some sort of Shakespearean or Greek tragedy and that I was misled by my wife and lived to extravagance, that is all nonsense," he told the BBC Radio 4 Today programme last month in his only British media interview since the guilty verdict in July.

When John Humphrys described his predicament as a “fall from grace”, Black quickly contradicted him, calling it “persecution” instead.

“He is still trying to maintain that narcissistic bubble he has been in, even now. He is casting himself as a romantic hero who has been victimised by the American justice system and the overzealous missionaries of corporate justice,” Mr Tombs said.

“He has the idea in his mind that going to prison is going to be a romantic exile. He will be in a Bavarian castle up in the Alps writing a seven-volume vindication of himself,” he said. “It’s not going to be like that at all. It’s just another one of those grandiose fantasies he has developed over the years. I do not see him really having the chance to write a 1,280-page book on Conrad Black when he is in prison that would be as serious and ponderous as his books on Roosevelt and Nixon.”

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