Once Conrad Black leaves a federal prison in Florida, free on bail pending an appeal of his conviction for defrauding investors, prosecutors could have a hard time if they have to prove their case against the former newspaper magnate a second time, legal experts say.
Black, 65, could be freed as soon as Wednesday, after U.S. District Judge Amy St. Eve in Chicago holds a hearing to determine the conditions of his release.
The former head of the Hollinger International media empire is more than two years into a 6 1/2-year sentence for defrauding investors out of millions of dollars and obstruction of justice.
The 7th Circuit U.S. Court of Appeals on Monday granted Black's motion for bail. The decision came weeks after the U.S. Supreme Court weakened the "honest services" law that was central to Black's fraud conviction and kicked his case back to a lower court. The justices left it up to the lower court to decide whether the conviction should be overturned. That decision has not yet been made.
Prosecutors said Tuesday that Black was unlikely to attend the Wednesday hearing, but they otherwise declined to comment on the case. And Black's attorney, Miguel Estrada, did not respond to phone messages Tuesday seeking comment.
Two legal experts not involved with Black's case but who have been watching it closely say the government could have a hard time putting him back behind bars once he's freed from the minimum security prison in Coleman, Fla., where he has been serving his sentence.
"It would be hard to put this case back together again," said Steven Skurka, an attorney who wrote a book about Black's trial. "You have someone who served two years. It's hard to refocus three years later. If the court ordered a new trial, Black would never see a courtroom again."
The appellate court's decision to release Black pending his appeal bodes well for him, said Marc Rothenberg, a former federal prosecutor who's now a white collar criminal defense attorney.
"In most criminal cases, courts don't grant bail pending appeal unless there's a likelihood that the conviction will be overturned on all the counts," Rothenberg said. "By the 7th Circuit ordering that Mr. Black be given bail and directing the district court to set those conditions tomorrow, they really have shown a sea change in their confidence in the jury's verdict."
The same appeals court rejected Black's appeal two years ago, before the Supreme Court decision. If the convictions are overturned, it's unlikely prosecutors will spend the time and energy to retry him, Rothenberg said.
Black and three former Hollinger International executives were convicted in 2007 of defrauding shareholders out of $6.1 million. One of the prosecutors' arguments was that Black deprived the company of his faithful services as a corporate officer, breaking the so-called "honest services" law.
Black also was convicted of obstruction of justice after jurors saw a video of him carrying boxes of documents out of his offices, loading them into his car and driving off with them. The documents were sought by government investigators. The high court's ruling didn't affect the obstruction of justice count.
Prosecutors are now tasked, in part, with convincing the appeals court that Black's obstruction of justice conviction should stand and that it should carry additional prison time. They could also argue that the jury based its fraud conviction on the evidence of so-called straight fraud, not on the "honest services" allegations, Rothenberg said.
Defense attorneys have argued that Black has already served more prison time than the obstruction count alone would have required.
If the appeals court overturns all of the counts of Black's conviction, prosecutors would have to decide whether to retry Black. The appeals court could also toss the fraud but keep the obstruction of justice count and order St. Eve to hold a new sentencing hearing.
"It's a good time to be a defense lawyer," Rothenberg said. "They had a lot of setbacks in this case and now they've got the better position."
Hollinger International once owned the Chicago Sun-Times, The Daily Telegraph of London, The Jerusalem Post and hundreds of community papers in the U.S. and Canada.
At the core of the charges against Black was his strategy, starting in 1998, of selling off the bulk of the small community papers, which were published in smaller cities across the United States and Canada.
Black and other Hollinger executives received millions of dollars in payments from the companies that bought the community papers in return for promises that they would not return to compete with the new owners.
Prosecutors said the executives pocketed the money, which they said belonged to shareholders, without telling Hollinger's board of directors.
But Black's lawyers have maintained that federal prosecutors failed to muster adequate evidence that he defrauded anyone or tried to hide key documents.
Black — who renounced his Canadian citizenship to become a member of the British House of Lords — was known for a grand lifestyle, including a $62,000 birthday party for his wife, a swanky apartment on Park Avenue in New York and a trip to the island of Bora Bora.
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