Conrad Black has lost a bid to have his remaining convictions dismissed on the basis that prosecutors "intentionally deprived" the former media baron of the ability to hire the defence lawyers he wanted.

The filing, made last year in a U.S. district court in Chicago, centred around claims that law enforcement's seizure of $9 million US of proceeds from the sale of his New York apartment left Black without enough money to retain lawyers Brendan Sullivan and Gregory Craig, who both worked at Williams & Connolly LLP in Washington.

'During the course of the pretrial proceedings and the trial, (Black) never informed the court that he was not represented by his counsel of choice.'—Illinois Justice Amy St. Eve

Black purchased the apartment from his company Hollinger in 2000 for $3 million and later sold it for $9 million. His lawyers argued that prosecutors deceived the court to obtain two warrants to seize the assets by concealing information that would have undermined their case for taking the money.

The former press magnate sold the Manhattan dwelling with the intent of paying for counsel to defend him against allegations of improper conduct at Hollinger International. Because the money from the sale wasn't available to Black, his lawyers argued he was denied his right to counsel.

Black said that without the money he couldn't afford the services of the two high-profile lawyers. Sullivan served as defence counsel for U.S. Marines Lt.-Col. Oliver North during the Iran-Contra scandal. Craig worked on Barack Obama's White House Counsel, represented John Hinckley, Jr. when he was acquitted of an attempted assassination of Ronald Reagan, and represented Goldman Sachs in 2010.

Key documents left out

On Tuesday, Illinois Justice Amy St. Eve — the same judge who presided over Black's initial fraud charges — denied the motion.

"It is worth noting that this case was hotly litigated from the beginning," Eve said in her decision.

"During the course of the pretrial proceedings and the trial, (Black) never informed the court that he was not represented by his counsel of choice."

The filing accused prosecutors of leaving out two key documents that contradicted their claims that Black defrauded Hollinger in setting a purchase price of $3 million for the apartment, the same amount Hollinger had paid for it initially, even though it had appreciated in value.

Black, who was released from prison last May, would have been cleared of two remaining fraud counts if his motion had been successful.

The initial filing stated that while it was too late to "turn back the clock" and allow Black access to his chosen lawyers, it was not too late to overturn his convictions.

Black served 37 months of a 42-month sentence in a Florida prison and returned to Canada last year under a special temporary permit, given that he is no longer a citizen.

In a highly publicized battle in 2001, he renounced his Canadian citizenship so he could accept a peerage in the British House of Lords.