Conrad Black faces possible return to prison in fraud case

Former press baron Conrad Black is bracing himself for a possible return to prison on Friday as a Chicago judge weighs up whether he must serve out the rest of his six and half year sentence.

The Canadian-born former press magnate and Tory peer was sent to jail four years ago on fraud and obstruction of justice charges. He served 29 months and has been free on bail for nearly a year after challenging his sentence following a law change relating to one of his convictions.

The former owner of the Telegraph newspapers will appear before justice Amy St Eve for re-sentencing. St Eve handed out his original sentence.

Legal experts argue that Black, 66, may struggle to stay out of jail. "I think she will reimpose the original sentence and he will have to serve the rest of his time," said attorney Andrew Stoltmann of Chicago-based Stoltmann Law.

Black's appeal focused on changes to the criminal code's definition of "honest services." Among Black's convictions were charges that he deprived shareholders of his "honest services" when he embezzled $6.1m (£3.8m) for himself and other associates at Hollinger, his media company.

The US supreme court tightened the definition of "honest services" last year, ruling that its use had become too broad and Black's conviction on those charges was overturned. But legal opinion suggests the fraud conviction that the court upheld – involving Black and others taking $600,000 from the company – had nothing to do with honest service but was straightforward theft.

St Eve will also consider Black's conviction on obstruction of justice. The peer and his chauffeur were videotaped taking boxes of documents from his Toronto office after a court had prohibited their removal.

Black was given 60 months for the fraud charges and 78 months for obstruction of justice, with both sentences to be served concurrently. St Eve could choose to uphold the original sentence, send him back to jail for a lesser time on the remaining convictions or allow him to stay free based on time served.

When re-sentencing, judges are obliged to consider a defendants' behaviour in jail and prosecutors have alleged that Black lorded it over his fellow prisoners. The peer treated fellow prisoners at Coleman Federal Correctional prison in Florida "like servants," according to sworn affidavits filed in court earlier this month.

Coleman staff claimed Black demanded special treatment, got prisoners to clean for him and do his ironing and was a poor tutor to his fellow inmates. In an email, Black said the accusations were "lies extorted by the prosecutors from susceptible Bureau of Prisons officials".

Stoltmann said St Eve could take the affidavits into consideration and had wide power of discretion in her sentencing. "Those are not the sort of opinions that you want hanging over you when you are asking a judge to shave time off your sentence," he said.