The Fall of an Arrogant Fraud: What Really Brought Down Conrad Black's Media Empire?

Conrad Black used to keep a picture of the Chicago gangster Al Capone on the silk-lined wall of Hollinger International's New York boardroom and would jokingly point him out to visitors as "our chief shareholder." Unlike Capone, who was convicted of tax evasion back in 1931, Black escaped a similar charge in Chicago on Friday. He was also cleared of eight other charges, including one of racketeering. Had there been a clean sweep of convictions, Black would have faced a prison sentence of almost 100 years. However, the former proprietor of hundreds of newspapers from Israel to the United States, Canada and the UK was convicted on three charges of fraud and one charge of obstructing justice, enough for him to be facing a fine of $1m and a jail sentence of 35 years.

This was not how Black had envisaged the outcome of the case. "Stage one were the ululations of joy at the so-called downfall," he had said earlier. "Stage two is the big battle ... And then stage three is where I win." Convinced that he has a special relationship with God, Black has always believed in his invincibility. He was inspired by such military heroes as Alexander the Great, Napoleon and General MacArthur, as well as by tenacious politicians such as as Churchill, Franklin Roosevelt, Nixon and Maurice Duplessis, the dictatorial leader of mid-20th-century Quebec.

In 2006, Black vowed that "we will bring this entire gigantic, malicious prosecution down around the ears of its authors." Throughout the trial he maintained a demeanor of comic-opera bravado, dubbing the US government prosecutors "Nazis" and telling reporters that the prosecution case was "hanging like a toilet seat around their necks."

The government failed to win convictions on the so-called lifestyle charges, relating to Black's expenses claims for his wife Barbara Amiel's lavish 60th birthday party at New York's La Grenouille restaurant in 2000 and for a 2001 trip to Bora Bora, Polynesia, for the two of them.

At the heart of the prosecution case were several controversial "non-compete" agreements arising out of the sale of Hollinger-owned newspapers in America and Canada. These payments were made by the buyers of the newspapers so as to prevent Black and his colleagues from setting up new titles in competition with them. Such payments, totaling approximately $60m, should have been paid to Hollinger, the government argued, but were instead diverted to the defendants. In the most blatant instance, the American Publishing Company (APC), a Hollinger subsidiary, paid Black and David Radler (his long-time business partner) almost $5.5 million, so that the two men were in the absurd position of paying themselves not to compete with themselves (in the event that they left Hollinger). Mark Steyn, a former employee of Black's and his chief journalistic champion, dismissed the APC payments as "a book-keeping wheeze dreamed up by David Radler that I'd wager Conrad wasn't even aware of until afterwards."

"If they are honest about it, the heart of their case was lost," said Edward Greenspan, Black's Canadian lawyer. "They lost on the big stuff." Bernard Harcourt, a professor of law at the University of Chicago Law School, strongly disagreed: "I think the verdict is a whopper. They got him on the four counts that mattered, the four that really make a difference." Jacob Frenkel, a former federal prosecutor and Securities and Exchange Commission enforcement lawyer, called it a "stunning victory" for the government and explained how a split verdict was in fact the best possible outcome for the prosecution since "it highlights for the appellate court that the jury was very thoughtful and thorough in its deliberations, separating the wheat from the chaff, identifying those counts in which the government met its burden of proof and those in which it failed to do so." Even Mr Steyn, Black's indefatigable supporter and -- some would say -- useful idiot, conceded: "The US Attorney's office might usefully adopt as its motto the IRA's message to Mrs Thatcher after the Brighton bombing -- 'You have to be lucky every time. We only have to be lucky once.'"