If you had to suffer the indignity of house arrest, you could do a lot worse than Conrad Black's estate at 1930 South Ocean Boulevard in Palm Beach, Florida. The sprawling 21,000–square–foot British Colonial-style residence sits on one of the most privileged stretches of real estate in the United States, with the Atlantic Ocean bordering one side of the property and the dark blue waters of Lake Worth lapping at the other. While awaiting his November 30 sentencing in Chicago—where the 63–year–old former chairman of Hollinger International faces up to 35 years in a federal prison—Black could play tennis on his private court, enjoy a refreshing dip in the pool, screen his favorite movie in the home theater, or reenact his own version of The Great Escape through the tunnel connecting his property to a 300–foot stretch of private beachfront. The only physical reminders of the newspaper baron's impending incarceration are the black iron bars that encircle the property to keep out those who want to catch a glimpse of corporate America's latest celebrity convict.
But while other fallen chieftains spend their final days of freedom gorging themselves on the vestiges of ill–gotten gains before the feds move in—picture the bloated, alcohol–tinged countenance of ex–Enron honcho Jeffrey Skilling—Black remains characteristically sanguine, ever the battle–tested general counting his casualties and awaiting reinforcements before launching his next attack. "It has been a four–year battle, and after the opening assault that I had pillaged the company for hundreds of millions of dollars, and the prolonged effort to impoverish me and imprison me for life, I feel I have steadily gained ground, and have an excellent basis for appeal," Black wrote to me in his first interview since a Chicago jury found him guilty of three counts of mail fraud and one count of obstruction of justice. "Being a historian, I am fairly familiar with the ups and downs of people's careers and may be able to assimilate a cataract of horrors better than some people." I had e–mailed him a long list of questions in August (on his lawyers' advice, he consented only to a written exchange, with his responses vetted by his legal team) about his thoughts on his criminal trial, his state of mind as he prepares for a lengthy prison sentence, and his feelings about his fallen media empire. Three days later, I received a 1,400–word response that was candid, thoughtful, and wholly unapologetic. Written in the bombastic, abstruse style for which he is famous, Black's statement displayed the fierce intellect responsible for his extraordinary rise—but also suggested the qualities responsible for his sudden, devastating fall.
Black's conviction ended a long saga at the company he cofounded in 1969 with the purchase of a small Quebec paper and transformed into the third–largest newspaper empire on the planet, with more than 500 papers including The Telegraphof London, the Chicago Sun–Times, and Canada's National Post. It all began more than four years ago, when a special committee appointed by Hollinger International's board of directors—headed by former SEC chairman Richard Breeden—accused Black and several of his associates of running a "corporate kleptocracy" that siphoned $400 million from shareholders. It continued when a grand jury corralled by U.S. Attorney Patrick Fitzgerald—the überprosecutor who scored a conviction against Lewis "Scooter" Libby—indicted Black on 14 counts of criminal fraud: racketeering, obstruction of justice, money–laundering, and mail and wire fraud. And it culminated on July 13 when the jury found him guilty on four of those counts.
