Conrad Black

In May 2004, Hollinger International, now free of Black's control, filed a $1.25 billion racketeering lawsuit against Black and other former corporate insiders, accusing them of pillaging the company of more than $400 million. In October, a judge dismissed the racketeering claims, and Hollinger refiled without them, adding Richard N. Perle as a defendant.

On November 15, 2004, the US Securities and Exchange Commission filed a civil fraud lawsuit against Black and Radler, alleging that they improperly diverted $85 million to their own use. In March 2005, the US revealed that it was also conducting a criminal investigation of Black and Radler.

In November 2005 federal prosecutors charged Black with eight counts of mail and wire fraud and accused of diverting $51.8 million of Hollinger shareholders money to himself and associates. Black rejects the charges.

On March 30, 2006, Black lost his battle to keep important documents away from US prosecutors in his fraud trial. U.S. District Judge Amy St. Eve, denied Black's motion to quash a subpoena to access 13 boxes of documents that Black removed from his Toronto office after he was notified that he was being investigated by the US Securities and Exchange Commission (SEC). Incriminating evidence showed a security video tape showing Black loading the boxes into his limousine on May 20, 2005, which was only hours after he was served a request for documents by the SEC which was investigating allegation that Black and other executives looted Hollinger International Inc. of more than $80 million dollars. 

Also on March 30, 2006, a report in the Globe and Mail claimed that the Internal Revenue Service wants banking records for a Barbados company that Black allegedly used to stash cash offshore. In 2004, a report from a special directors committee of Hollinger International alleged that Black used the Barbados company, Argent News Inc., "to avoid taxes on some of the millions he is accused of skimming when he was the company's chairman". 

On April 13, 2006, The Guardian published a story in which it claims that Hollinger International Inc. has agreed to pay the majority of Black's legal bills. Black had argued that the company should provide 100% of his legal fees and filed a law suit demanding advances to cover his costs in March 2004. Intrestingly under the settlement, Black would be forced to repay the money if it is determined that he is not indemnified by the company's insurance policy.