Black controlled Hollinger International, once the world's third-largest English-language newspaper empire, which published The Daily Telegraph (UK), Chicago Sun-Times (U.S.), The Jerusalem Post (Israel), National Post (Canada), most of the leading newspapers in Australia and Canada and hundreds of community newspapers in North America, before controversy erupted over the sale of some of the company's assets.
Black was born in Montreal, Quebec, to a well-to-do family originally from Winnipeg, Manitoba. His father, George Montegu Black, Jr., a Chartered Accountant, became the president of Canadian Breweries Limited, an international brewing conglomerate that had earlier absorbed Winnipeg Breweries. Conrad Black's mother was the former Jean Elizabeth Riley, a daughter of Conrad Stephenson Riley, whose father founded The Great-West Life Assurance Company, and a great-granddaughter of an early co-owner of The Daily Telegraph. His father was a shareholder in the Daily Telegraph.
Biographer George Toombs said of Black's motivations: "He was born into a very large family of athletic, handsome people. He wasn't particularly athletic or handsome like they were, so he developed a different skill – wordplay, which he practiced a lot with his father." Black has written that his father was "cultured humorous" and that his mother was a "natural, convivial, and altogether virtuous person." Of his older brother George Montegu Black III (Monte), Black has written that he was "one of the greatest natural athletes I have known", and that though "generally more sociable than I was, he was never a cad or even inconstant, or ever an ungenerous friend or less than a gentleman.". The Black family maintains a family plot at Mt. Pleasant Cemetery in Toronto where Black's parents and brother are buried along with his good friend and his wife's former husband, journalist, poet and broadcaster, George Jonas.
Black was first educated at Upper Canada College (UCC), during which time, at age eight, he invested his life savings of $60 in one share of General Motors. Six years later, he was expelled from UCC for selling stolen exam papers. He then attended Trinity College School in Port Hope, where he lasted less than a year, being expelled for insubordinate behaviour. He did successfully complete the year as an extramural student.
Black went on to a small, now defunct, private school in Toronto called Thornton Hall, continuing on to post-secondary education at Carleton University (History, 1965). He attended Toronto's Osgoode Hall Law School of York University, but his studies ended after he failed his first year exams. He completed a law degree at Université Laval (Law, 1970), and in 1973 completed a Master of Arts degree in History at McGill University.