Conrad's Black week

The 62-year-old former owner of the Daily and Sunday Telegraph newspapers has been enjoying a luxurious stay at the swanky Ritz Carlton hotel in Chicago during his 15-week trial in the city.

But now he may be measured for an orange prison jumpsuit if the verdict goes against him and he is convicted of swindling £30million from shareholders.

The steely, defiant expression that the immaculately dressed multi-millionaire has shown to the world throughout the trial has finally given way to signs of stress and anxiety as the grim reality of his predicament dawns on him.

As he stepped into a cab outside the Ritz Carlton last week, he suddenly looked careworn and vulnerable.

As the jury considers its verdicts for a second week, Lord Black is wrestling with a new problem — what to do if state prosecutors attempt to seize the remnants of his tattered empire.

For guilty verdicts could mean up to 20 years in jail, fines of $7 million (£3.5million) and a state action to seize his assets.

In the absence of the jury, prosecutors gave lawyers for Lord Black and his three former executives and co-defendants details of future forfeiture plans if he is found guilty of tax fraud.

Documents already filed to the district court in Chicago allege that Lord Black has “prop­erty constituting and derived from proceeds obtained, directly and indirectly, from racketeering activity, which property is subject to forfeiture”.

All his stock interests and interests in several companies are in the firing line, plus “at least $92,000,000 including but not limited to the $8,558,035 that represents the net proceeds from Black’s sale of the second floor apartment that was seized by the US in October 2005 and Black’s residence at 1930 Ocean Boulevard in Palm Beach, Florida, both of which are pledged to secure Black’s bond in this case.”

Lord Black has already sold his London home for a reputed £13million, but retains a mansion in his native Toronto.

Meanwhile, more problems are on the horizon.

Lord Black and his associates face a class action lawsuit in Canada next September from shareholders who lost fortunes in his newspaper empire because of alleged swindling.

Canadian lawyer Evatt Mer­chant said tens of thousands of people from three provinces would be seeking hundreds of millions of Canadian dollars.

“They are white collar shareholders who have lost from their retirement nest eggs. This is not a victimless crime.”

Lord Black also faces a £271million lawsuit from the Sun-Times Media Group, the new name given to his old company Hollinger International.

But for now he is trying to guess the jury’s assessment of the 13 counts against him, mostly alleging massive fraud.

During the past months the jury has been given a detailed insight into how Lord Black controlled his empire, once the third largest newspaper company in the English speaking world with titles including the Daily and Sunday Telegraphs in Britain, the Jerusalem Post, the National Post in Canada and the Chicago-Sun Times in the US.

In a uniquely complex financial system, he set up a pyramid of companies with himself as head.

Prosecutors accused him of using Hollinger International as a  piggy bank to fund a lavish lifestyle for himself and Lady Black, his 66-year-old journalist wife.

Their apparent extravagances became a sideshow in the trial prompting Edward Greenspan, Lord Black’s lawyer, to comment: “In America you can’t convict someone for being rich.”

Key witness for the government was Lord Black’s former right-hand man David Radler, 64, former publisher of the Chicago Sun-Times, who has done a deal with prosecutors to serve a 29-month term in a soft Canadian jail in return for giving evidence.

Most of the evidence focused on so-called non compete payments during a mass sell-off of news­papers to cover debts.

Prosecutors argued that Lord Black’s parent company, Ravel­ston, was used to siphon off millions of dollars.

Whichever way the verdict goes, Chicago will not forget Lord Black.