The Extravagant Fall of Conrad Black

Whe

n the Sherbrooke Record, a small Canadian paper, fell into the hands of a young Conrad Black and his partner in 1969, few could have predicted the new owner's meteoric rise. But just decades later, Montreal-born Black — still with David Radler, that right-hand man, at his side — had built a media business stretching the globe. And as chairman and chief executive of Hollinger International, then publishers of newspapers from the Chicago Sun-Times to London's Daily Telegraph, Black reveled in his status. Boasting swank homes in London, New York and Florida, he and his glamorous wife swaggered between glitzy parties on both sides of the Atlantic. Black even cashed in his Canadian citizenship to become a British Lord in 2001.

These days, Black and Radler are still closely tied — but for very different reasons. Beginning Wednesday, a federal court in Chicago will hear charges of fraud, racketeering and obstruction of justice against 62-year-old Black. And after cutting a deal with prosecutors, Radler will take the stand against his former boss. Black — whose reign as chairman and CEO had ended by 2004 — denies all charges, but if found guilty, could spend the rest of his life locked up. "I know I am innocent of the allegations against me," Black wrote in Tatler magazine recently. "And I am about to prove it."

Prosecutors — led by U.S. Attorney Patrick Fitzgerald, fresh from sealing the perjury conviction of White House aide I. Lewis "Scooter" Libby — allege Black used the publicly owned Hollinger as a piggy bank, skimming off millions of dollars of shareholders' money. Three other former Hollinger execs are also accused. Central to the case are charges that after the sale of many of Hollinger's titles beginning in 1998, Black and the other execs pocketed fees paid by the newspapers' new owners to ensure Hollinger wouldn't compete with the titles it had dumped. That money should have been divvied among shareholders, prosecutors say; Black insists the payments were above board.

Black is also accused of billing the firm for eye-watering personal expenses, from seats at the opera to using the company jet for a vacation on the Pacific island of Bora Bora. Add that, prosecutors say, to a $40,000 claim for his wife's birthday celebrations at a plush restaurant in New York. "This is one of those cases where there's so much wrongdoing, in so many different areas, that the most difficult thing is keeping track of it all," said Jay Eisenhofer, a U.S. lawyer who will argue a separate civil case against Black, in a BBC documentary on the mogul broadcast Tuesday. "On a scale of 0-10, with 10 being the worst example, I think you'd find that Conrad Black is probably somewhere around 50."

Nonsense, Black would argue — "it will be a relief to expose my accusers and their parrots and their false charges," he predicted in Tatler — but his rise and sudden demise is prompting no shortage of vitriol. Black is "a spoilt, intelligent, overbearing performer, who recklessly believed that the laws are for the little people and that he could always, on the basis of his entitlement to wealth and power, ignore the normal rules of society," says Tom Bower, author of Outrageous Fortune: The Rise and Ruin of Conrad and Lady Black. Since that book was published in November, Black has sued the author for almost $10 million, accusing Bower of portraying him as a "criminal sociopath."

And though she's not on trial, Black's wife, conservative columnist Barbara Amiel, has come under scrutiny, too. Famed for her free-spending ways — she once quipped to Vogue that "my extravagance knows no bounds" — and dubbed Lady Macbeth in sections of the British media, Amiel bewitched Black, Bower tells TIME, to the point he "was blind, willfully blind that he couldn't afford what he wanted to provide her with."

If love, betrayal and excesses weren't dramatic enough, there's still the prospect that high-profile former Hollinger board members like Henry Kissinger could make cameo appearances as witnesses. The trial is expected to last three months.