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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, according to Tom Bower's biography Dancing on the Edge, he was expelled from UCC for selling stolen exam papers.
He then attended Trinity College School where he lasted less than a year, being expelled for insubordinate behaviour.
Black eventually graduated from a small, now defunct, private school in Toronto called Thornton Hall, continuing on to post-secondary education at Carleton University ( History, 1965 ).
For a time, he attended Toronto's Osgoode Hall Law School of York University ; however, 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.
Black's thesis, later published as a biography, was on Quebec premier Maurice Duplessis.
Black had been granted access to Duplessis ’ s papers, housed in Duplessis ’ s former residence in Trois-Rivières, which included “ figures from the famous Union Nationale Caisse Electorale ( the party war chest ), a copy of the leader of the Opposition ’ s tax returns, gossip from bishops ,” as well as “ historically significant letters from Cardinal Jean-Marie-Rodrigue Villeneuve side-by-side with hand-written, ungrammatical requests for jobs with the Quebec Liquor Board, unpaid bills, the returns of his ministers who were cheating on their taxes, a number of scribbled notes for Assembly speeches, tidbits of political espionage, compromising photographs, a ledger listing the political contributions of every tavern-keeper in the province .” Black subsequently had the principal items from the papers copied and microfilmed, and donated copies to McGill, York, and Windsor universities.

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