Whether he will want to jump back into the world he once dominated is unknown, but those who have followed his rise and fall from grace say Black could still wield influence, though likely not at a public company.
Black himself has indicated he's done with the type of scrutiny that comes with running a publicly traded company following the demise of Hollinger International Inc.
"The regulators, the minority shareholders, all that crap. Oh, I can't stand it," he told Vanity Fair in an interview before returning to jail last August to serve the remaining nine months of his prison term.
Karl Moore, a professor at McGill University's Desautels Faculty of Management, said Black is unlikely to be involved in a publicly traded company, but he could quietly act as a consultant or adviser.
"I think there might be some business people — you know former colleagues or former peers — that might be willing to do some business with him because he has a very sharp mind," Moore said.
"I suspect if he were going back in business it would be maybe in private equity or the advising business where he would not be in the limelight in the same way, but they could harness his considerable business ability."
"If he needs to, if he wants to financially, I think there would be some limited opportunities," Moore added.
Black's holdings were once worth hundreds of millions of dollars and included control over the Chicago Sun-Times, the Daily Telegraph of London and newspapers across Canada and the United States.
Black — who is reportedly returning to Canada after being granted a one-year temporary resident permit — was convicted five years ago of fraud and obstruction of justice following accusations of siphoning $6.1 million of shareholder money and removing key documents.
Despite the convictions, Richard Powers, a professor of business law at the University of Toronto, said Black's business acumen has never been questioned.
Powers noted that during a recent business discussion he attended, about a third of those there said they would want Black sitting on their board.
"No one has ever said that he didn't have certain skill sets, but those skill sets come with a bit of notoriety," Powers said.
"Do you want a convicted felon working in your business? That's why I think anything he does get involved in will be private and likely around continuing his writing and publishing."
When Hollinger sold the bulk of its Canadian newspapers in 2000, the industry had yet to see its business radically transformed by the Internet.
Blogs were still in their infancy, while Facebook, Twitter and other social media that dominate the space were non-existent. Craigslist had yet to devour the lucrative classified advertising business.
But since then, newspapers have seen revenues drop as readers turn to the Internet and social media for the latest news.
Canwest Global, the broadcasting giant which bought the bulk of Black's Canadian holdings, has been dismantled and sold off in pieces with the newspapers now held by Postmedia Network.
But a comeback in newspapers isn't out of the question.
David Radler, Black's former business partner who testified against him at his trial, has been running the Alberta Newspaper Group, a privately held newspaper chain, since his release from prison.
Once known for throwing lavish parties and jet-setting to homes on both sides of the Atlantic, Black has said that he "can live on $80 million" in an apparent reference to what remains of his wealth.
He has also said that he plans to continue to write. Black remains a contributor to the comment page of the National Post, the newspaper he founded in 1998.
Black's latest book, a memoir titled "A Matter of Principle", is a 2012 National Business Book Award finalist. He has also been busy writing columns for the Huffington Post and National Post.
In a 2010 interview with the BBC, when asked if he'd get back into the news business, Black said: "Not as a chief occupation and not in a public company, but it might happen."
It was New York investment firm Tweedy Browne that first started asking questions as a shareholder about management fees paid to a firm owned by Black and Radler that started the downfall.