[2] The special committee's report contained allegations of impropriety which led to a criminal investigation and, ultimately, the unraveling of the Hollinger media empire.

[4] Black was called before the U.S. Securities and Exchange Commission in December 2003 but he refused to answer questions about business dealings, citing his Fifth Amendment right against self-incrimination.

[5] In May 1998, American Trucker Magazine (ATM) was sold by Southam (see also Hollinger International Inc.) in a bundled transaction including a daily circulation Western Canada newspaper for $93,672,000.

[8] In February 2004, Delaware judge Leo E. Strine, Jr. barred the Barclays sale and wrote in his judgment, "Black breached his fiduciary and contractual duties persistently and seriously...

[10] In August 2004, a special committee of the Board of Directors of Hollinger International Inc. made a report of investigation to the U.S. Securities and Exchange Commission and the U.S. District Court.

The special committee was headed by Richard Breeden, a former SEC Chairman who was paid approximately $100,000 (USD) per week for his work.

[12] In November 2004, the SEC filed civil fraud lawsuits against Black and several others, alleging the defendants cheated and defrauded shareholders through a series of deceptive schemes and misstatements.

However, former federal prosecutor and SEC enforcement lawyer Jacob Frenkel called it a "stunning victory" for the government and explained how a split verdict "highlights for the appellate court that the jury was very thoughtful and thorough in its deliberations.

"[21] Investigators hired by Hollinger companies to locate assets examined more than forty bank accounts which may be, or may have been, held in the name of Black, his wife, or affiliated entities.

[23] In November 2007, Sun-Times Media Group (formerly Hollinger) said in a regulatory filing that it had spent $107.7 million on legal fees and indemnification costs for criminal and civil actions involving Black, Boultbee, Kipniss and Atkinson.

Were he to regain residency, "Canadian citizenship can't be granted to those who are criminally inadmissible and neither the minister nor the Governor in Council (cabinet) can override that," according to an immigration department spokesperson.

[26] Black's oral arguments were heard June 5, 2008, by a three-judge panel of the United States Court of Appeals for the Seventh Circuit.

The circuit court found that "the evidence established a conventional fraud, that is, a theft of money or other property from Hollinger by misrepresentations and misleading omissions..." The panel affirmed the jury's findings stating that, "It is not as if Black had merely been using his power as controlling shareholder to elect a rubber-stamp board of directors or to approve a merger favorable to him at the expense of the minority shareholders ...

[11] Prosecutor Eric Sussman replied to news of the initial appeal decision saying, "I think at some point in time Mr. Black needs to take a hard look in the mirror and ask who it is that really doesn't understand the conduct that took place in this case…You've got 16 people who have taken a look at the facts and the law in a very detailed and time-consuming way, and they have all reached the same conclusion, which is that he stole money from this company and he tried to obstruct the investigation.

"[31] Black added Harvard professor Alan Dershowitz to his law team and asked the 7th Circuit Court to reconsider the appeal decision without success.

Eric Sussman, Black's prosecutor in the Chicago trial, told the Toronto Star that the Supreme Court's rejection of Black's bail request means that the "Supreme Court is confident that no matter what happens he's still going to be serving six-and-a-half years for obstruction of justice" regardless of the outcome of his appeal.

Writing for the Court, Justice Ginsburg was critical of Judge Posner's decision, referring to its "anomalous" ruling and the "judicial invention" found therein.

On May 31, 2011, the Supreme Court of the United States refused to grant Black leave to appeal his two remaining convictions without any comment.

Although he has given up his Canadian citizenship in 2001 in order to receive British peerage, he has expressed desire to live in Canada after his prison term completed.

Critics denounced that Black received special treatment from the Canadian government but Stephen Harper, the Prime Minister, denied any political influence.