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On Friday, November 20, 1981, a businessman little known to the outside world sent a limo to collect Andy Warhol from Toronto airport. "It took us to the Four Seasons Hotel and I had suite 2910 overlooking all of Canada," the celebrated artist noted in his diary. "Mr Black is about 37, and sort of heavy, very nice, and a nice fortune — they have mines and supermarkets and newspapers."

Black had thrown a party for Warhol at the Art Gallery of Ontario. An early indication of his assumption of celebrity and greatness followed: Warhol was commissioned to produce four portraits of the young Black — now dotted across his troubled empire.

Black was hardly a star: he ran a small chain of Canadian daily newspapers and had some investments in retail and industry. He grew up in Toronto, the second son of George Black, a bright but difficult executive at Canadian Breweries, which was owned by the Argus Corporation, a Canadian holding company with investments ranging from mines to supermarkets to media companies. His mother, Jean Elizabeth Riley, known as Betty, had been a champion skater and came from a prominent, well-heeled family.

Black says in his autobiography that they were an "almost improbable pair whose private conjugal abrasions were sometimes saddening, often hilarious". His father was complicated and aloof, his mother straightforward and affable. As they got older, Black says they became ever more eccentric; she would go to bed after dinner and he'd sit up for much of the night brooding — "rarely unfortified by a generous spirit issue".

George and his son Conrad had plenty in common. History and politics were their favourite topics of conversation. They disagreed on one issue: America's wartime president Roosevelt, the subject of Black's recent 1,280-page biography, Champion of Freedom. Black Senior considered Roosevelt a menace and a socialist. For Conrad, he was the greatest American of the 20th century.

Black's long-held obsession with Roosevelt stretches back to when, as a 10-year-old, he used to love playing recordings of the president's speeches. On one occasion his father threatened: "If I hear that sewer's voice again in this house, I'll smash the records. Do you hear me, damn it?"

George Black retired at 48 after a row with his boss, but remained a big Argus shareholder and board member. Conrad was steeped in the lore of the company, with his father mapping out the web of Argus's corporate entities for them as if he were mapping out Napoleon's forces.

Conrad hated school, describing the staff at Upper Canada College as "sadists", "fondling homosexuals" and "swaggering boobies". At an early age he was exposed as a thief who was prepared to steal to fuel his ambition and his finances: at 14, he was expelled for selling exam questions he had stolen from a school office. It was 1959 and in a few hours he pocketed $1,400, enough to keep a Canadian family for months.

After a brief bohemian period, in which he worked as a Paris tour guide, Black got a degree in French civil law from Laval University in Quebec, following it with a master's in history. Soon afterwards he published his first book, a biography of Maurice Duplessis, Quebec's reactionary premier whose reputation for pomposity was soon to be matched by Black's. His friend Henry Jackman says he should have been a man of letters, a writer. "He is not really interested in being a businessman at all." But his father had other ideas.

In 1969, George Black and other principal shareholders formed Ravelston, a private holding company representing half of Argus's voting rights. George Black had become an increasingly reclusive and bitter figure. His final words to his son, according to Peter Newman, Black's first biographer, were: "Life is hell, most people are bastards and everything is bullsh**." After his father's death, he found books on depression in his father's library that had been heavily underlined.

Black was appointed to the boards of Argus and Ravelston in his father's stead. Aged 33, he pulled off a takeover of Argus that caused Fortune magazine to christen him "the boy wonder of Canadian business". Tutored by his father, Black knew that under the original 1969 Ravelston contract, any shareholder who amassed 51% of its shares could force the remaining stockholders to sell him theirs. Black held 22.4%. He enlisted the support of two women — the widow of Argus's former chairman and her sister, who together controlled another 47.2% — and took over. The widows got $10m each and Black got control of a company with $4 billion in assets.

The new, brash, young Argus president suddenly acquired a Rolls-Royce, a private jet and a lifestyle that demanded a suite at Claridge's when he was in London. Black dabbled in local newspapers, and began building the foundations for his expansion beyond Canadian shores.