Conrad Black will have his bail hearing early Wednesday in Chicago, following Monday's decision by an appeal court that he be released, pending a review of his fraud convictions.
In a brief notice Tuesday, Judge Amy St. Eve set the bail hearing for 8:45 a.m. Wednesday. Black does not need to be present for the hearing and is expected to have his lawyers speak on his behalf.
For now, Black remains in a federal prison in Coleman, Fla. Once St. Eve sets the bond and its conditions, it's possible the former media baron could be free by Wednesday afternoon.
It's not known what conditions the court will set, but James Morton, a professor at Osgoode Hall Law School and past president of the Ontario Bar Association says it's possible Black will be allowed to leave the U.S.
"Since really, he is not a flight risk – he did surrender voluntarily and as always obeyed the orders of the court -- it's likely he'll be given fairly generous terms of release," Morton told CTV News Channel Tuesday.
"My sense is he'll be obliged to post a fairly significant bond, but once that bond is posted, he will be permitted to return to Toronto," he added.
Others however predict St. Eve will be tough on the former media baron and restrict his movements outside of the U.S. St. Eve was the U.S. District Court judge who sent the former media mogul to jail after presiding over his trial in 2007.
Black has served just over two years of a 6 1/2-year sentence for fraud and the more serious charge of obstruction of justice.
Law ‘too vague'
An appellate court decided on Monday that Black should be released on bail while a U.S. appeals court reviews his convictions. The decision came just weeks after the U.S.
Supreme Court ruled that the "honest services fraud" law that was used to convict Black was too vague. That sent the case back to a lower court. A decision on the matter still hasn't been made.
The top court narrowed the definition of the law. Previously, the "honest services" law could be used to convict corporate executives who took bribes, kickbacks or had a conflict of interest in their business dealings.
It was the conflict of interest angle that was used to convict Black. But, that prosecution has been removed from the law. Now, a successful "honest services fraud" conviction hinges upon allegations of bribery and kickbacks, neither of which were involved in the Black case.
Jacob Frenkel, a former federal prosecutor and expert in white-collar crime, says he believes Black will not return to jail any time soon.
""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 told The Canadian Press.
Even Black's obstruction conviction won't likely dampen his freedom, he said.
Black was convicted of obstruction of justice after a security video showed the newspaper baron carrying boxes of documents out of his downtown Toronto office.
Those documents were wanted by government investigators.
The high court's ruling doesn't affect the obstruction charge.
Nonetheless, Frenkel said that Black had already served a ‘reasonable' amount of his sentence to cover the charge.
"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."
However, the criminal case is just one of the many legal hurdles Black has been forced to contend with. Black also faces civil actions from creditors and investors from past business dealings.
Perhaps more daunting, however, was a ruling issued by the Internal Revenue Service last week over back taxes. The IRS stated that Black owes US$70 million in back taxes, because he failed to pay any tax on $116 million worth of earnings between over a five-year period ending in 2003.
The IRS is also pursuing Black's former business partner, David Radler, publisher of the Chicago Sun-Times under Black's newspaper chain Hollinger Inc.
According to Forbes, the IRS says Radler also failed to file returns for the same years, paid nothing on $111 million in taxable income and owes $66 million.
Model prisoner
Black is considered a model prisoner at the Coleman Federal Correctional Complex, teaching English to his Hispanic inmates and learning how to play piano.
He also unexpectedly took up a cause behind bars, urging an end to America's war on drugs, penning letters to London's Sunday Times newspaper.
He is one of 1,000 prisoners at the facility, most of whom are serving time for drugs or weapons offences.
He has described his inmates as "quite interesting and affable," likening his experience in prison to his time at a Toronto boarding school.
Black, who famously denounced his Canadian citizenship to become a member of the British House of Lords, was known for his expansive vocabulary and penchant for lavish living.
He was accused of funding his lifestyle with shareholders' money but Black's lawyers have maintained that federal prosecutors failed to come up with evidence proving he defrauded anyone or tried to hide key documents.
