The son of a wealthy Canadian brewery boss, Conrad Moffat Black showed his first sparks of rebellion as a teenager when he was expelled from an exclusive private school for selling stolen exam papers.
He entered the media business in 1969 by buying a local paper, the Sherbrooke Record, with his friend David Radler. Within a decade, the pair had a successful chain of papers and they hit the big-time in 1985 by buying the Telegraph titles in Britain — giving Black the international voice he craved.
At the height of his success, Black had an estimated fortune of £136m, with homes in Florida, New York and Kensington.
But he attracted enemies as well as friends: the Canadian government blocked him from accepting a peerage in Britain, prompting Black to revoke his citizenship in 2001.
During the trial, Black's own lawyers admitted he could be an unsympathetic character with a fondness for "rhetorical musings" which made him sound "snotty".
He has written several acclaimed biographies including books on Richard Nixon and Franklin Delano Roosevelt.
Black married the writer Barbara Amiel in 2002. He has three children - Jonathan, James and Alana - from a previous marriage.
As his legal troubles mounted, Black moved back from Britain to his childhood home in the wealthy Toronto suburb of Bridle Path.