The fallen media mogul must navigate a thicket of thorny immigration procedures in order to accomplish his stated goal of reclaiming the Canadian citizenship he renounced over a decade ago.
That quest will be hampered by his criminal convictions, lawyers said, adding the former head of Hollinger International shouldn't expect his marriage to a Canadian citizen or the end of his 3.5-year jail term to help advance his case.
Joel Sandaluk, partner with immigration firm Mamann, Sandaluk and Kingwell LLP, said Black's pending citizenship will be as complex, unusual and uncertain as his previous clashes with the North American justice system.
"I've been doing this for a lot of years now, and I've never, ever met anybody who has renounced their citizenship and is trying to re-enter Canada," Sandaluk said in a telephone interview.
"The reality is this whole case, from an immigration and citizenship perspective, is operating in kind of a netherworld. I don't think anyone knows exactly what to expect."
Black was born in Montreal, but gave up his citizenship in 2001 after being offered a peerage in Britain's House of Lords. Then prime minister Jean Chretien forbade him from accepting the role while he held a Canadian passport.
Sandaluk said that decision — made before his legal woes began in the U.S. — means Black must be treated as any other foreign national when applying to move back to Canada full time. Black can only be considered as a potential citizen after attaining permanent residency status and living in the country for at least a year.
Permanent residency, however, seems unlikely due to Black's criminal record, Sandaluk said.
Black's controversial business dealings while at the helm of Hollinger's global media empire netted him fraud and obstruction of justice convictions in 2007 and saw him spend several years in a Florida prison.
Although he will complete his sentence and be released on Friday, Sandaluk said his two convictions make him criminally inadmissible for residency in Canada.
Black's only recourse, he said, is to apply for a temporary resident permit _ a document that essentially stands as permission from the federal minister of citizenship and immigration.
"What (the permits) basically are meant to be is a cure-all for any form of inadmissibility," Sandaluk said, adding the document would allow Black to come to Canada for anything from an overnight visit to a prolonged stay.
The Supreme Court of Canada made the need for the permit clear earlier this month when handing down a ruling on an unrelated libel case. The decision specified that Black could not re-enter the country without "the special permission of the Minister of Citizenship and Immigration even once he has finished serving his sentence."
Sandaluk said a temporary resident permit would be all the permission that's required, adding Immigration Minister Jason Kenney will not have to weigh in personally.
Kenney's spokeswoman Alexis Pavlich said the minister has no plans to get involved in Black's case.
"At the minister’s instruction, this decision will be made solely by departmental officials, with no input from the minister or his office," Pavlich said. "This decision will be made by highly trained and professional public servants applying Canada’s immigration laws.
Black has stated in previous media interviews that he hopes to return to Toronto, where he and wife Barbara Amiel still own a home. His calendar reportedly already includes an engagement in his home town.
Black's memoir "A Matter of Principle" is one of three nominees for the 2012 National Business Book Award, and media reports suggest Black plans to be in attendance when the winner is announced on May 28.
Sandaluk said it's impossible to speculate on the success of Black's efforts to obtain a temporary resident permit, since such decisions are notoriously arbitrary.
All things considered, however, Sandaluk said the facts are in Black's favour.
"He doesn't seem like a threat to the public safety of Canada, he doesn't seem like somebody who's going to reoffend while he's here," Sandaluk said.
"My suspicion would be that he should be able to get a temporary resident permit. That being said, because of the notoriety of this case, really all bets are off."
Note to readers: This is a corrected story. An earlier version said Black was born in Toronto.