Exactly one year into his 6½-year sentence in a Florida prison for fraud and obstruction of justice, Conrad Black awaits news for when he might get another day in court.
Lawyers for Montreal-born Black petitioned the U.S. Supreme Court in January to review his guilty verdict to assess whether the prosecution's argument that Black deprived shareholders of the honest services they were owed is a legitimate one.
Black was convicted in Chicago last year of a $6.1-million fraud and obstruction of justice related to his eight-year spell as head of Hollinger International Inc.
The Supreme Court is expected to rule on the matter by March 13, and a longtime friend of Black's, Brian Stewart, said the former media baron remains optimistic about the possibility of clearing Black's name if the court agrees to hear his appeal.
But Jacob Frenkel, a former U.S. prosecutor who has followed the case, said the bid is unlikely to succeed.
Unlike lower courts, the Supreme Court must agree to hear a case, which means Black's petition is fighting to get through a door "with such a small crack that the likelihood of getting in is negligible," Frenkel said.
"Statistically, the likelihood of the Supreme Court agreeing to review is marginally better than the likelihood his sentence will be commuted — and both are around nil."
Decision 'not tainted,' lawyer says
Toronto lawyer James Morton said he would "be astonished" if the Supreme Court accepted Black's petition.
"The jury legitimately could have found that there was theft of company money, so there is a supportable basis for the jury's decision which is not tainted in any way by any legal argument," Morton said.
"Since the jury's decision is supportable on the facts, why would the Supreme Court take this case where it's muddy to clarify an area of law that's really not all that unclear anyway?"
Media baron upbeat
Stewart said Black has managed to make his time in the Coleman Federal Correctional Complex in Coleman, Fla. not only bearable, but intellectually stimulating by using his skills to teach other inmates, write books and articles, read and learn to play the piano — an activity his mother didn't let him indulge in as a child.
"I don't think in any way one would have predicted so positive a year, in terms of creative activity and mental occupation," Stewart said.
A year ago, he said, "it was still an unknown what he would be facing, and I think what has happened over this year is a pleasant surprise, in the fact that he's been able to utilize his talents and his drive in a creative way to the degree he has."
Black is generally upbeat, on top of current events and keeps busy with several activities, including answering "an enormous" amount of correspondence.
He doesn't like to dwell on the tougher aspects of being in prison, because "he knows how damaging that kind of internal anger can be and he doesn't want to go there," Stewart added.
"But I wouldn't say for one second he's not an angry man: He's intensely disappointed and angry at the … judicial system."
Empire in ruins
Black's biggest frustrations, he added, is what he considers the destruction of his former Hollinger International media group — now Sun-Times Media Group Inc. — since charges were brought against him more than three years ago.
The company, which in Black's late-1990s heyday ranged from the Victoria Times Colonist to the Montreal Gazette, the London Telegraph, the Jerusalem Post and a host of trade publications, has shrivelled into a rump of U.S. Midwest community newspapers around the tabloid Chicago Sun-Times.
"He believes he was railroaded by a preposterous prosecutorial system in the United States and that he remains an innocent person and is absolutely determined to prove his innocence," Stewart said.
Doug Pepper, Black's publisher at McClelland & Stewart, said Black's mood has been as good as it can possibly be under the circumstances and that he's making the best of his time.
Pepper has been dealing with Black as he finished his upcoming book, The Fight of My Life, the second part of his memoirs. The book deals in part with Black's time in jail, as well as the trial and other challenges since his first autobiography was published in 1993.
"He's not only a really, really great writer, he adheres to schedule as well if not better than any writer I've worked with," Pepper said.
"He is certainly not letting this beat him or get him down."
Black's time in jail hasn't come without hardships like dreary living conditions and menial work, but he also hasn't had any trouble with other inmates or guards, and sees his wife Barbara Amiel Black as often as possible.
"There were a lot of unkind comments about Barbara and I hope it's been since shown that in questions of loyalty she's been quite remarkable," Stewart said.
In past interviews, Black has maintained he was doing fine at Coleman, which he called "a safe and civilized place."
"I am optimistic that one way or another, justice will prevail," he wrote at one point during is his stay.
Eric Sussman, the Chicago prosecutor who led the case against Black and is now in private practice, said he was glad to hear Black was making effective use of his time behind bars, but added that doesn't change the outcome of the trial or his reasons for prosecuting.
"I hope that while he is in there and doing things with his time, that one of the things that he thinks about are the shareholders of Hollinger Intentional," Sussman said.
"The things that killed that company were paying tens of millions of dollars in legal fees as Mr. Black fought the company tooth and nail and refused to accept responsibility for what he had done."
Sussman said he was also confident the Supreme Court would reject Black's request for an appeal, noting that four different judges that have thus far upheld the jury's verdict.
Morton noted the whole ordeal could have been avoided if Black had apologized at the outset and offered to repay back any money that seemed inappropriate.
His downfall, he added, was the tenacious way in which he held to his innocence.
"One of the things that any competent lawyers tells clients is that principles are too expensive," Morton said.
"You deal with the problem rather than the concept of justice in the abstract."
Black's former business associate David Radler was paroled late last year from a Canadian jail after serving 10 months of a 20-month prison term for fraud he received after he testified against Black.
Black never had the option of serving his time in Canada because he had renounced his Canadian citizenship to become a member of the British House of Lords.
Co-defendants Peter Atkinson and Jack Boultbee are both scheduled to be released from prison next year. Former Hollinger lawyer Mark Kipnis was also found guilty but sentenced to house arrest.