CHICAGO — Competing portraits of Conrad Black – once one of the world's most powerful media moguls – will be on display Friday in Chicago at his resentencing hearing, where a judge will decide whether he heads back behind bars or remains free for good.
The Canadian-born businessman is a devil-may-care elitist who looks down his nose at the rest of humanity, according to prosecutors; and a gentleman, unbowed by adversity, who quietly has gone about helping others, counters the defense.
Which portrayal U.S. District Judge Amy St. Eve accepts may factor into her ruling about whether to return Black to a Florida federal prison for several more years or, as his lawyers have asked, to resentence him to time already served.
The resentencing is a climax of a long legal saga for Black, 66, who rubbed shoulders with the rich and powerful before his fall to disgrace, convicted in 2007 and sentenced to 6 1/2 years for defrauding investors in Hollinger International Inc.
Black, whose empire once included the Chicago Sun-Times, The Daily Telegraph of London and small papers across the U.S. and Canada, was freed on bail after serving two years to let him to pursue what would be partially successful appeals.
The 7th U.S. Circuit Court of Appeals in Chicago last year tossed out two of Black's fraud convictions but upheld a conviction for fraud and one for obstruction of justice. And it said Judge St. Eve would have to sentence Black again for those two standing counts.
Despite the nullified counts, prosecutors are asking St. Eve to hand the burly, silvery-haired Black the same 6 1/2-year sentence she originally meted out in 2007, meaning he would have to spend about 4 1/2 more years in prison.
"He 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," prosecutors said in a recent filing.
Black's lawyers, in turn, have accused government attorneys of vindictiveness.
In filings of their own, they say the fervor prosecutors have shown in justifying the stiffer sentence displays "a drive-by disparagement of Mr. Black which reveals nothing but the intensity of the governments dislike for him ..."
A major point of contention Friday is likely to be accounts of Black's behavior during his two years in prison.
The defense argues Black was a model prisoner, noting that the accomplished biographer – whose subjects have included Franklin D. Roosevelt and Richard Nixon – helped teach inmates American history and economics; and gladly offered advice about business and other matters to prisoners who constantly approached him.
"In a place where hope is a rare commodity, Conrad provided at least a glimmer of it to countless inmates," one inmate wrote in a letter, cited by the defense in a recent filing.
Prosecutors say the defense paints too rosy a picture of Black's prison life.
One prison employee, Tammy Padgett, claimed in an affidavit filed by prosecutors that Black had arranged for inmates – "acting like servants" – to clean and cook for him, to iron his clothes, mop his floor and perform other chores.
Another employee told her that Black once insisted that she address him as "Lord Black," after an honorary title bestowed on him by Britain, Padgett added.
The defense denied both characterizations.
After his conviction, the defense showed letters from such celebrities as Sir Elton John, describing Black as someone who had devoted much of his life to helping charities. It's not clear if his attorneys will roll out similar letters vouching for Black on Friday.
His big chance to squash the convictions arose in June of 2010, when the U.S. Supreme Court sharply curtailed disputed "honest services" laws that underpinned part of Black's case. The appellate court that reversed two of Black's convictions cited that landmark ruling.
But the appellate judges said the one fraud and obstruction of justice convictions were not affected by the Supreme Court's ruling. The fraud conviction, the judges concluded, involved Black and others taking $600,000 and had nothing to do with honest services: It was, they asserted, straightforward theft.
Defense lawyers have criticized honest services laws as vague and a last resort of prosecutors when they couldn't show money changed hands. Watchdogs countered they were key to fighting white-collar and public fraud.