THE CANADIAN PRESS -- TORONTO - Conrad Black will learn whether his days of wearing orange jumpsuits and sleeping in a cell are behind him Friday when he appears in the same Chicago courtroom where he was sentenced four years ago.

The Canadian-born former press magnate, who has been free on bail for nearly a year, will appear in front of U.S. Justice Amy St. Eve at a resentencing hearing Friday morning that will determine his fate.

But even if Black, 66, emerges a free man, it's unlikely he'll ever clear his name because he remains a convicted felon, according to legal experts who have been following the case.

"He's going to come out of court on Friday when the judge does not impose additional jail time, and he's going to claim victory," said white collar crime expert and former prosecutor Jacob Frenkel.

"If someone views being a convicted felon on two counts and having served 29 months a victory, then let him call it a victory."

St. Eve sentenced Black in 2007 to spend 6 1/2 years in prison for three fraud convictions and another for obstruction of justice. He was handed down 60 months for the fraud charges and 78 months for the obstruction of justice conviction, with both sentences to be served concurrently.

Carolyn Gurland, Black's lawyer, said she couldn't make any predictions about the case, but added is hopeful going into it.

"We are certain that the court has taken careful account of all the filings and hopeful that the court will reject the government's vindictive arguments," she said.

The two sides have recently ramped up a war of words in legal filings as the defence tries to paint Black a model inmate, while prosecutors portray him as an abusive snob.

Black, who has exhausted all legal avenues after a last ditch Supreme Court appeal was denied in May, will continue to have a criminal record stemming from two standing convictions. Full exoneration will take nothing short of a presidential pardon.

"This is the final chapter," said Steven Skurka, a Canadian criminal lawyer who has written a book about Black's case.

"He's not fully exonerated, but if you consider where the government's case started and the fact that Black was looking at spending the rest of his life in jail, it represents a huge defeat for the government but Black can not claim total vindication either."

Black had already served 2 1/2 years in a federal penitentiary in Coleman, Fla., before being released on bond last July awaiting an appeal after a landmark Supreme Court ruling that exposed flaws in a federal fraud law that had been a favourite of white-collar crime prosecutors.

The length of Black's sentence will be up for debate Friday. Judge St. Eve could choose to uphold the original 6 1/2 year sentence, send him back to jail for a lesser time on the remaining convictions, or allow him to stay free based on time served.

The June 2010 Supreme Court ruling lifted Black's fortune, by setting aside his three mail fraud convictions alongside a ruling on former Enron CEO Jeffrey Skilling in limiting the use of a federal fraud law that has been a favourite of white-collar crime prosecutors — known as the "honest services" argument. They sent the ruling down to a lower court to decide how it applied to Black.

An appeals court in October reversed two of his fraud convictions, then a three-judge panel in Chicago unanimously rejected Black's request for a rehearing of his appeal on the remaining fraud and obstruction counts.

The fraud conviction, the judges found, involved Black and others taking $600,000 and had nothing to do with honest services: It was, they concluded, straightforward theft.

The high court's ruling didn't affect the more serious obstruction of justice count. It was laid after jurors saw a videotape of him carrying key documents sought by the U.S. Securities and Exchange Commission out of his Toronto office and driving off with them.

Andrew Stoltmann, a Chicago lawyer who has been following Black's case believes the remaining charges are so serious that he is headed back to jail serve the entirety of the rest of his term.

"The remaining fraud and obstruction of justice convictions are very serious, and warrant a 6.5 year sentence of their own," he said.

Stoltmann noted that resentencing judges are also charged with considering a defendants behaviour in jail. Recent affidavits from Coleman prison officials claiming that Black shirked his tutoring duties and used other inmates as servants will hurt his chances of escape, he said.

"The claims that Black ‘lorded’ over other inmates, making them iron his shirts and treating other prisoners like servant are not allegations Black will want hanging over his head going into the re-sentencing."

But Frenkel said St.Eve has probably has her mind made up about what to do with Black ahead of the actual hearing Friday. Still, both sides have to be careful not to anger the judge and Black will have to appear deferential and acknowledge that he served time for a reason.

"The judge is interested in what is a reasonable sentence given the offences for which the conviction has survived, not about the sniping as to who was carrying food trays in the cafeteria," he said.

Black is the former CEO of Hollinger International, which once owned the Chicago Sun-Times, the Daily Telegraph of London, the Jerusalem Post and hundreds of community papers across the United States and Canada.

More recently, he has been prisoner at Coleman, where he's been one of 1,000 criminals, most of them convicted of drug or weapons offences.

Black was originally charged with more than a dozen criminal allegations, most accusing him or his associates of siphoning $6.1 million away from the publicly traded company and to themselves or private companies they controlled.

Sunny Freeman, The Canadian Press