Will Conrad Black go back to jail?

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Conrad Black is bracing for a possible return to prison on Friday but says he is prepared for any outcome, including rebuilding his business career and returning to Canada.

Lord Black has been out of prison for roughly a year while pursuing various appeals of his criminal convictions for fraud and obstruction of justice. All the appeals have been exhausted and now Chicago Judge Amy St. Eve will decide Friday whether Lord Black should head back to prison to finish all or part of a 6½-year sentence. The hearing marks the final chapter in what has been a prolonged and precedent-setting case that stretched all the way to the U.S. Supreme Court and fundamentally changed U.S. fraud laws.

"If I am sent back, it will not be for very long," Lord Black wrote in an e-mail to The Globe and Mail. "I do feel that I will ultimately win the battle, as the poverty of the government's case is clear and we got rid of their [fraud]statute. We took down all 17 of their counts and two were revived by a real exercise in gymnastics by the appeal panel chairman."

While the legal battle raged, Lord Black's newspaper empire collapsed into bankruptcy and nearly all of his business holdings have been sold or wound up. His health has deteriorated as well and he still faces a host of civil lawsuits. Despite all that, Lord Black vows he'll make a comeback.

"I live to fight another day and rebuild [my]career, all of which is unusual when someone is attacked as violently by the U.S. government as I have been. I won't be surprised by much and am ready for anything, and am hopeful," he wrote.

Lord Black, 66, was originally convicted in 2007 of three counts of fraud and one count of obstruction of justice over the misappropriation of $6.1-million (U.S.) at Hollinger International Inc., once one of the largest newspaper companies in the world. He has served 29 months of his sentence at a prison in Florida. He was released on bail last year after an appeal to the Supreme Court resulted in a reinterpretation of a key part of the fraud statute. That decision and further appeals led to the reversal of two fraud convictions connected to $5.5-million of the misappropriation.

Judge St. Eve must now resentence Lord Black on the two remaining convictions. A presentence report from probation officials has recommended a sentence of between 33 and 41 months.

Lord Black's lawyers argue he should be released for time served. In court filings they say he was a model prisoner, tutoring dozens of inmates, helping many others and offering lectures on American history and social economics. He also wrote a book while in jail, called The Strategic History of the United States, and was a featured speaker at the prison's African-American History Day. They also note that prison has diminished Lord Black's health, leaving him with high blood pressure and early signs of skin cancer. His wife, Barbara Amiel Black, is also in poor health and requires heart surgery, court filings show.

"Mr. Black's ability to rise above adversity in such a productive and dignified manner not only underscores the quality of his character, it helps to demonstrate why additional prison time is not needed to achieve the purposes of sentencing," Lord Black's lawyers say in court filings.

Prosecutors argue Lord Black should return to jail to complete his term. They say he has shown no remorse and continues to protest his prosecution. Lord Black "fails to acknowledge his central role in destroying Hollinger International through greed and lies, instead blaming the government and others for what he describes as an unjust persecution," they argue in filings. Prosecutors also question whether Lord Black was such a model prisoner and they filed statements from prison officials who allege Lord Black asked for special treatment and "gathered a following of inmates who performed services for him, acting like servants."

They also note that the appeal court "barely" reversed the two fraud convictions and that the appeal judges "emphasized the propriety of this court's continuing to hold [Lord Black]accountable for the [conduct related to the other charges]at this resentencing."

Lawyers who have followed the case are divided on the outcome of Friday's hearing.

"I don't think there's much of a question that he's going to go back to jail," said Chicago lawyer Andrew Stoltman. He said Lord Black's original sentence included more time for obstruction than for fraud. Lord Black received three years for each fraud charge and 6½ for obstruction, all served concurrently. "That obstruction-of-justice charge, that's a serious charge," he said. He believes Lord Black will return to prison for another year.

Chicago lawyer Hugh Totten doubts Lord Black will, or should, go back to jail. "How is justice going to be served by putting Conrad Black back in jail for more incarceration time?" he asked.

If Lord Black is released Friday, it isn't clear where he will go. His bail conditions have required him to remain in the United States throughout the appeals. Recently he has been living in New York and he has sold his Florida mansion. If he is given time served, U.S. immigration officials have told the court that he is "out of legal status," which means he could be held for deportation. Or he could remain free on probation under the same conditions as his bail and apply to return to Canada.

Getting back into Canada won't be easy. Lord Black still has a home in Toronto but he gave up his Canadian citizenship years ago to become a British citizen in order to sit in the House of Lords. Lord Black's lawyers have been working on an application for immigration status in Canada, but they can't do much until after the resentencing.

When asked if he was confident of returning to Canada, Lord Black replied: "Yes."

................................................................................................................................................................................................................................................................................................................................... Where are they now?

What other players in the Black saga are up to

David Radler: Conrad Black's right-hand man cut a deal and testified against Lord Black and other Hollinger executives. In return, Mr. Radler pleaded guilty to one fraud charge and received a 29-month sentence. He served seven months in the United States, transferred to Canada in 2008 and was released on parole after 10 weeks. He now runs Vancouver-based Alberta Newspaper Group.

John Boultbee: Hollinger's former chief financial officer was convicted on three fraud charges in 2007. He received a 24-month sentence, served 11 months in the United States and was released on bail in 2009 pending appeals. Two fraud charges have been reversed, and he has been resentenced to time served. He lives in Victoria.

Peter Atkinson: Hollinger's former vice-president and general counsel was also convicted of three fraud charges in 2007 and received a 27-month sentence. He initially did not join the appeal to the U.S. Supreme Court, preferring to push for a transfer to Canada. That happened in 2009 and he was released shortly afterward. He later joined the appeal and two fraud charges were reversed. He was resentenced to time served and lives in Toronto.

Mark Kipnis: Hollinger corporate counsel convicted of one fraud charge in 2007. He received five years of probation. The charge was reversed on appeal. Mr. Kipnis lives in Chicago and runs a sign business.

Hollinger: Once one of the largest newspaper companies in the world, Lord Black's Hollinger empire has crumbled since the fraud allegations surfaced in 2003. The major holdings - Hollinger International Inc., Hollinger Inc. and Ravelston Corp. Ltd. - all filed for bankruptcy protection and have been sold or wound up.