Conrad Black faces resentencing in Chicago

The long-running legal saga of a once-powerful media mogul whose newspaper empire spanned several continents reaches a climax on Friday when a federal judge decides whether to send him back to prison or let him remain free based on time served.

Prosecutors who brought the fraud case against Conrad Black, 66, have depicted him as a devil-may-care elitist who looks down his nose at the rest of humanity. The defense counters he is actually a gentleman, unbowed by adversity, who quietly goes about helping others.

Which portrayal U.S. District Judge Amy St. Eve accepts may factor into her ruling on whether to return Black to a Florida federal prison for several more years or, as his lawyers have asked, to resentence him to time served.

A jury convicted Black in 2007, and St. Eve at the time sentenced him to 6 ½ years for defrauding investors in Hollinger International Inc.

But Black, whose empire once included the Chicago Sun-Times, The Daily Telegraph of London, The Jerusalem Post 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 ½-year sentence she originally meted out in 2007, meaning he would have to spend about 4 ½ 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, saying their justification for a 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.

But 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.

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.