Skip to content

Chicago judge to set Conrad Black free on bail

CHICAGO — Conrad Black’s six-year prison sentence could come to an early end Wednesday exactly where it was handed down — in a courtroom in the American city where the

CHICAGO — Conrad Black’s six-year prison sentence could come to an early end Wednesday exactly where it was handed down — in a courtroom in the American city where the disgraced Canadian-born media mogul was convicted of fraud and obstruction of justice three years ago.

A U.S. District Court judge, the same one who presided over Black’s trial and sentenced him to a six-and-a-half year sentence in 2007, will outline Black’s bail conditions, which are expected to confine the former newspaper baron to the United States.

But it’s very possible that Black’s days as an inmate are over, said Jacob Frenkel, a former federal prosecutor and an expert in white-collar crime.

“It is reasonable to expect that Mr. Black will walk out of the U.S. penitentiary some time on Wednesday and possibly never return,” Frenkel said.

It remained unclear Tuesday where Black would be when Judge Amy St. Eve makes her pronouncement; it’s likely he will remain behind bars in Coleman, Fla., until St. Eve sets bond and bail conditions, and not appear in Chicago, appeal lawyer Miguel Estrada said in an email.

The 7th Circuit U.S. Court of Appeals granted Black’s motion for bail Monday, weeks after the U.S. Supreme Court weakened the “honest services” law that was central to his fraud conviction and kicked his case back to a lower court.

The justices left it up to the lower court to decide whether the conviction should be overturned. That decision has not yet been made.

Black also was convicted of obstruction of justice after jurors saw a video of him carrying boxes of documents out of his offices, loading them into his car and driving off with them. The documents were sought by government investigators. The high court’s ruling didn’t affect the obstruction of justice count.

It’s possible he’s already served enough time to cover that charge, said Frenkel.

“Even if the obstruction of justice conviction survives, as most expect, the length of time he has served already is considered by most federal judges to be reasonable for such a conviction.”

Black has, by all accounts, been a model prisoner at Coleman, where he’s been one of 1,000 criminals, most of them convicted of drug or weapons offences.

The former Canadian citizen, convicted of defrauding Hollinger Inc. of more than $6 million, was born into a life of luxury. He’s a renowned historian known for an expansive vocabulary. And yet for more than two years, he’s been Prisoner 18330-424, eating his meals in the prison mess hall, teaching English to his Hispanic fellow inmates, and learning how to play the piano.

The one-time conservative also took up an unexpected cause while behind bars, urging an end to America’s war on drugs.

“The U.S. is now a carceral state that imprisons eight to 12 times more people (2.5 million) per capita than the U.K., Canada, Australia, France, Germany or Japan,” Black wrote in a letter to the Sunday Times of London in November 2008.

“U.S. justice has become a command economy based on the avarice of private prison companies, a gigantic prison service industry and politically influential correctional officers’ unions.”

In his letter to the Times, Black also described his fellow inmates as “quite interesting and affable, often in a Damon Runyon way,” adding his time in prison was “a little like going back to boarding school, which I somewhat enjoyed nearly 50 years ago.”

Black attended Upper Canada College, an elite all-boy school in the heart of Toronto’s lavish Forest Hill neighbourhood, but was expelled as a teen for selling copies of stolen exam papers.

But while Black is soon to be enjoying a measure of freedom, he’s still facing several civil suits. The U.S. Internal Revenue Service also recently launched a US$71 million lawsuit for alleged unpaid taxes.

Black is challenging the IRS’s claim, arguing that he was “neither a citizen nor a resident of the United States” and therefore not obliged to pay taxes in the U.S.

The IRS’s case against him harkens back to a far grander period in Black’s life, alleging he failed to report and pay taxes on income stemming from personal use of Hollinger’s corporate jets, the use of corporate money to buy the papers of former President Franklin D. Roosevelt, and Hollinger’s purchase 10 years ago of a US$5.9-million New York apartment for his use.

Hollinger International once owned the Chicago Sun-Times, The Daily Telegraph of London, The Jerusalem Post and hundreds of community papers in the U.S. and Canada.

At the core of the charges against Black was his strategy, starting in 1998, of selling off the bulk of the small community papers, which were published in smaller cities across the United States and Canada.

Black and other Hollinger executives received millions of dollars in payments from the companies that bought the community papers in return for promises that they would not return to compete with the new owners.

Prosecutors said the executives pocketed the money, which they said belonged to shareholders, without telling Hollinger’s board of directors.

But Black’s lawyers have maintained that federal prosecutors failed to muster adequate evidence that he defrauded anyone or tried to hide key documents.

Black, who renounced his Canadian citizenship to become a member of the British House of Lords, was known for a grand lifestyle, including a $62,000 birthday party for his wife, a swanky apartment on Park Avenue in New York and a trip to the island of Bora Bora.