Former media tycoon Conrad Black will face a U.S. federal court judge on Friday to learn whether he must return to prison for fraud and obstruction of justice convictions.

Lawyers for Black, 66, and the U.S. government are to present their arguments at a resentencing hearing in Chicago to Judge Amy St. Eve, who presided over Black's original trial in 2007.

The Montreal-born Black was serving a 6½-year sentence in a U.S. prison when he was freed last summer after the U.S. Supreme Court curtailed the "honest services" laws used to convict him of defrauding Hollinger International investors.

An appeals court subsequently reversed two convictions but upheld two others — on fraud and obstruction of justice.

The Supreme Court rejected an appeal of those convictions in May, meaning Black won't be cleared of the charges but could remain free if St. Eve decides to allow him time served on the counts.

The U.S. attorney believes Black's original sentence of 6½ years should be reimposed and filed documents in advance of Friday's hearing detailing the testimony of two prison workers who suggested Black wasn't the model inmate his defence lawyers have portrayed.

In one document, a unit manager at the Coleman prison complex in Florida said Black demanded special treatment and gathered an entourage of inmates who acted as servants for him. In another filing, an education specialist who supervised Black as a tutor, claimed he was haughty and uninterested in those duties.

Black's defence team has claimed in its filings that his contributions to the community through teaching and tutoring at Coleman "were nothing short of extraordinary."

Black's empire once included the Chicago Sun-Times, the Daily Telegraph of London and smaller papers across the United States and Canada.

In her resentencing decision, St. Eve will follow guidelines established by a U.S. commission that aims to provide uniformity across sentences.

Legal observers suggest several possible scenarios:

Time served: Black has served 29 months of his original 6½-year sentence in U.S. federal prison, and St. Eve is unlikely to be swayed by either side's claims about his behaviour while incarcerated, said Jacob A. Frenkel, a criminal lawyer and former U.S. prosecutor based in Maryland.

"Judge St. Eve will acknowledge that information, but at the end of the day it will make absolutely no difference," Frenkel told CBC News's Mike Hornbrook.

"The fact that he served 29 months, I think the judge will consider that to be satisfaction of his punitive obligation."

Probation: Assuming the judge does not send Black back to jail, he will likely have a period of probation and be required to report by telephone periodically, Frenkel added.

Black is unlikely to face additional supervisory obligations, since he will not be considered a violent offender or a high risk of being arrested again, said Donald Allen, a law professor at Chicago's Northwestern University.

Deportation: If sentenced to time served, Black is subject under U.S. law to being detained and immediately facing deportation proceedings. But Frenkel said it's safe to assume there have been discussions between prosecutors and Black's attorneys about a scenario that would allow him a voluntary approach to his immigration status as a result of his conviction.

Black, who previously expressed a desire to return to Canada, no longer holds Canadian citizenship, having famously renounced it to accept a British peerage. He would need special permission — either an extradition agreement or ministerial order — to return to Canada.

Immigration Minister Jason Kenney's office said it could not comment on the specifics of any case "or on hypotheticals."

"I can say that every case is assessed by highly trained public servants based on the law, the Immigration and Refugee Protection Act," Kenney's spokeswoman Candice Malcolm said in an email to CBC News.

Similar sentence: According to Allen, the decision by the appeals court in Black's case implicitly suggested the original sentence handed out by St. Eve was the norm.

"My guess is that this is going to be a lot of hollering and shouting over nothing, and he's going to get a similar sentence," Allen said of Friday's hearing.

In that case, Black would face a definite sentence, which under U.S. law means he must serve at least 85 per cent of it — with time reduced only for good behaviour.