Lord Black of Crossharbour, the disgraced media baron and former Daily Telegraph proprietor, is facing not only a prison sentence but a renewed legal onslaught by the US authorities that could financially ruin him.
Tomorrow the peer goes back to court in Chicago, where he was found guilty in July of fraud and obstruction of justice. Apart from a jail term, he is likely to have a multimillion-dollar fine imposed on him, but he also faces the resurrection of a civil lawsuit to claw back millions in ill-gotten gains that could leave him with nothing.
As part of the criminal case, prosecutors are already trying to seize the Palm Beach mansion where Black has been holed up with his wife, Barbara Amiel, for the past five months. The judge, Amy St Eve, will decide in the morning whether he should forfeit the property, which the US government alleges was renovated using cash stolen from the peer's stock market-listed company, Hollinger International. Prosecutors also want $8.5m (4.2m) in proceeds from the sale of his New York apartment. The FBI seized the cheque before it was handed to Black.
Now, financial regulators are planning to come after the peer for more money they say he stole from his Hollinger International newspaper company, putting pressure on a fortune that has already been whittled down by legal fees. The civil lawsuit, filed by the Wall Street watchdog, the Securities and Exchange Commission, was frozen in 2005 when it became clear that the peer would be facing criminal charges.
In recent days, however, SEC lawyers have restarted work on the case, demanding documents from Black and pursuing revelations made during his 14-week criminal trial earlier this year. A court hearing has been set for 20 December, when a judge will decide how quickly the two sides must prepare witness statements ahead of a trial, in perhaps a year's time.
George Tombs, a Canadian biographer of the convicted peer, said: "It looks like a one-two punch, with the criminal case to destabilise him and lock him up, and then another case to go after him and ruin him."
Black's lawyers failed to have the SEC's case thrown out two years ago. The regulator says he should pay back his share of $85m taken out of Hollinger using bogus business deals, and then pay tens of millions of dollars more in damages. Earlier this year, his business partner of three decades, David Radler, paid the SEC a settlement of $37m, days before testifying against the peer in the criminal case.
Legal experts say Black is likely to be allowed a final Christmas with his family before being told to report to prison in the new year. Prosecutors will argue he should spend up to 24 years in jail, but a pre-sentence report suggested a term nearer to five years. The peer told Canadian TV this week that "prison would be a bore, but quite endurable".
The prison: Peer to plead for a prison without fences
Black will plead with the judge, Amy St Eve, to be allowed to serve his sentence in a minimum-security jail close to the Canadian border, to cushion the blow of swapping his life of luxury for a prison dormitory. While non-Americans are not usually allowed to serve their time in the lowest-security institutions, Black's lawyers say that the disgraced peer is neither planning to abscond nor likely to be a risk to the public.
Rather, he is planning to immerse himself in writing and his continuing legal fight, and a location close to Canada would allow easy visits not just from his family but also from his lawyers. A minimum-security jail would impose fewer restrictions on his movements and, unlike a low-security prison, it would have no armed perimeter patrols and possibly no fence at all.
For the fallen media baron, the change of lifestyle will be harsh. Whatever the security level of the prison, inmates are required to work at tasks such as washing windows or mopping floors.
The fines: The treasures the tycoon stands to lose
Black could well lose his beloved 21,000-acre colonial-style beachfront home in Palm Beach, Florida, if a Chicago judge decides tomorrow that much of its $35m (17m) value derives from improvements he made using money stolen from his media empire.
Black's family home in northern Toronto was lavishly redecorated by him and his wife, Barbara Amiel. Its most ostentatious features include an 18th-century cardinal's throne and a domed library allegedly modelled on St Peter's in Rome.
The Manhattan apartment was one of the first assets to go as legal bills mounted, shutting a venue for the Blacks' lavish parties, where they had wooed New York's billionaire business set. Prosecutors seized the $8.5m proceeds, and the court must decide tomorrow whether he will forfeit that money.
Art, antiques and books
The Blacks were prodigious collectors of the finest books, artworks and antiques. Prosecutors titillated the jury at the peer's trial with details of extravagances such as a $12,500 shaving cabinet and a porcelain bottle that Napoleon used during his Russia campaign.Reuse content