He has written eleven books, mostly in the fields of Canadian and American history, including biographies of Quebec premier Maurice Duplessis and US presidents Franklin D. Roosevelt, Richard Nixon and Donald Trump, as well as two memoirs.

[13] He attended Toronto's Osgoode Hall Law School of York University, but his studies ended after he failed his first year exams.

Black had been granted access to Duplessis' papers, housed in Duplessis' former residence in Trois-Rivières,[16] which included "figures from the famous Union Nationale caisse électorale (the party war chest), a copy of the Leader of the Opposition's tax returns, [and] gossip from bishops",[6] as well as historically significant letters from Cardinal Jean-Marie-Rodrigue Villeneuve and Paul-Émile Léger, Governor General Field Marshal Alexander, Lord Beaverbrook, Canadian and French Prime Ministers and Eminent Canadian and American finance ministers 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, [and] a ledger listing the political contributions of every tavern-keeper in the province.

Black described Amiel, in the first volume of his autobiography as "beautiful, brilliant, ideologically a robust spirit" and "chic, humorous and preternaturally sexy".

Thereafter, he "approached Rome at a snail's pace", and began to study the writings of Roman Catholic thinkers such as St. Augustine, Thomas Aquinas, Cardinal Newman, and Jacques Maritain.

Argus controlled large stakes in five Canadian corporations: Hollinger Mines, Standard Broadcasting, Dominion Stores, Domtar and Massey Ferguson.

[25] Through his father's position at Canadian Breweries, and his status as a co-founder of Ravelston, Black gained early association with two of Canada's most prominent businessmen: John A.

[26] Interviews with the two sisters in their retirement homes in Florida were aired 21 September 1980 in the episode of the CBC's The Canadian Establishment, entitled "Ten Toronto Street".

[6] Other observers admired Black for marshaling enough investor support to win control without committing a large block of personal assets.

Black resigned as Chairman of Massey Ferguson company on 23 May 1980, after which Argus donated its shares to the employees' pension funds, both salaried and union.

"[34] Journalist and writer George Jonas, the former husband of Black's wife, Barbara Amiel, contended that Hollinger made its "investors ... billions [of dollars]".

Five years later, he bought The Jerusalem Post, and by 1990, his companies ran over 400 newspaper titles in North America, the majority of them small community papers.

Hollinger International shares were listed on New York Stock Exchange in 1996, at which time the company boosted its stake in Southam to a control position.

[20] Becoming a public company trading in the US has been called "a fateful move, exposing Black's empire to America's more rigorous regulatory regime and its more aggressive institutional shareholders".

[42][43] Black agreed to the demand but citing such fees was standard procedure in the newspaper industry and had been requested by buyers and had been properly disclosed.

[42] Breeden involved the US Attorney in Chicago, and Radler, after about 18 months, would promise to plead guilty to one count of fraud and to provide evidence against Black and others in exchange for a light sentence in Canada.

He has called claims that his wife charged personal expenses to a corporate account, including US$2,463 (£1,272) for handbags, $2,785 for opera tickets, and $140 for Amiel's "jogging attire"[5] fiction and has pointed out that they were never alleged at trial.

[66] Black was initially found guilty of diverting funds for personal benefit from money due to Hollinger International, and of other irregularities.

[71] On 24 June 2010, the US Supreme Court ruled 8–0 with one recusal, instructing the 7th Circuit to review all four of Black's convictions including the obstruction of justice charge, finding that the definition of honest services fraud used in Judge St. Eve's (the trial judge) charge to the jury in Black's case was too broad, "unconstitutionally vague",[72] ruling the law could apply only to cases where bribes and kickbacks had changed hands and ordered the US 7th Circuit Court of Appeals in Chicago to review three fraud convictions against Black in light of the Supreme Court's new definition.

Black was to appear once again in a Chicago court on 16 August to provide full and detailed financial information to the judge, who would then consider his request to be allowed to return to Canada while on bail.

[citation needed] On 17 December 2010, Black lost an appeal as to fact and law on his remaining convictions for fraud and obstruction of justice.

[88] On 30 June 2011, Black published an article for the National Review Online that provided his scathing view of the legal case, detailing it as a miscarriage of justice and an "unaccountable and often lawless prosecution".

[100] Once the review process started, Black submitted a written application in defence of keeping his place in the Order of Canada, but failed in his efforts to persuade the advisory council he should appear before them to defend his case orally.

[102] In an October 2012 interview, Black intimated that he would rather resign from the order than be removed: "I would not wait for giving these junior officials the evidently almost aphrodisiacal pleasure of throwing me out.

[112] The Washington Post noted, "In addition to his book, Black frequently writes columns praising Trump and considers the president a friend".

[114] In July 2013, the Ontario Securities Commission restarted its case against Black and two other former Hollinger executives, John Boultbee and Peter Atkinson.

[118] In mid-May 2016, it was revealed that the CRA had intervened to prevent the sale and lease-back, with a buy-back option, of Black's home on Park Lane Circle.

After discussion, the sale-lease back proceeded and Black provided other assets as security pending the settlement or adjudication of the CRA claim.

[119] On 14 June 2019, the Tax Court of Canada ruled that Black is entitled to deduct interest expenses on a $32.3 million loan he used to satisfy judgments against himself and Hollinger International.

[125] In an interview with Peter Mansbridge in May 2012, Black said he would consider applying for Canadian citizenship "within a few years", when he hoped the matter would no longer be controversial and he could "make an application like any other person who has been a temporary resident".