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Miguel Estrada, lawyer for Conrad Black, centre, talks with reporters outside theU.S. Supreme Court on Tuesday in Washington.

Evan Vucci/The Associated Press

After six years of legal battles, the fate of jailed media baron Conrad Black is now in the hands of nine U.S. Supreme Court judges, who are expected to decide by June whether to reverse his conviction for fraud.

The top court's decision will not only affect Lord Black, but could also have an impact on hundreds of other cases - including an appeal by former Enron chief executive Jeffrey Skilling - and change the way American justice officials go after white-collar crime.

The judges spent about an hour Tuesday grilling Lord Black's lawyer, Miguel Estrada, and deputy solicitor-general Michael Dreeben, who represented the U.S. government. Each judge peppered the lawyers with detailed questions, sometimes cutting them off in mid-answer.

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The hearing, in an ornate chamber surrounded by 24 soaring columns, rows of red curtains and four marble engravings, was packed with onlookers including Lord Black's wife, Barbara Amiel-Black, and his daughter, Alana. Both sat at the back of the packed chamber on one of the dozens of long benches. Several lawyers who had worked on the case over the years were also among the roughly 200 spectators.

Lord Black was convicted in 2007 of fraud and obstruction of justice in Chicago and he was sentenced to 6½ years in prison. His case is one of three the Supreme Court has selected to review a controversial provision in the U.S. anti-fraud statute known as "honest services." The others are appeals by Mr. Skilling and a former Alaska legislator.

The court usually selects one case on a topic for review, and the fact that the judges have picked three indicates they have trouble with the law, legal observers say. That came through Tuesday, as several judges pummelled Mr. Dreeben with questions about the scope of "honest services."

The concept has been a tricky legal issue for nearly 40 years. Prosecutors began using it in the 1970s to convict corrupt politicians of fraud, arguing they had deprived the public of its intangible right to good government and honest services. Their efforts ground to a halt in 1987 when the Supreme Court ruled prosecutors had gone too far and that the anti-fraud law did not include intangible rights such as honest services.

Congress was furious and quickly added a one-sentence amendment to the statute to include violations of "honest services." Since then prosecutors have used the amended law to take on dozens of corporate crime cases such as Enron as well as Lord Black and other former executives of Hollinger International Inc. Critics say the honest-services concept is too broad and criminalizes far too much conduct.

Mr. Estrada focused on that Tuesday, beginning the hearing by arguing that the law should be struck down because it was "vague, amorphous and open ended."

"This case must be reversed," Lord Black's lawyer told the court. Referring to the court's 1987 ruling, Mr. Estrada said: "This court asked Congress to speak clearly and Congress did not." Several judges picked up on that theme, focusing their questions on just how far the law could be interpreted.

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Mr. Justice Stephen Breyer, for example, asked whether the law could be applied to someone who spent some time at work reading the Daily Racing Form instead of doing his job. Is that a deprivation of honest services, the judge wondered. There are about 150 million workers in the U.S., Judge Breyer told Mr. Dreeben, adding: "140 million of them would flunk your test."

Madam Justice Sonia Sotomayor asked whether someone who skipped work to go to a baseball game would be covered by the statute. And Mr. Justice Antonin Scalia hinted that the law is confusing and appeared to be limitless.

Mr. Dreeben, the government lawyer, fended off the tough questioning by arguing that there were several long-standing precedents, known as materiality, that guided prosecutors and prevented frivolous prosecutions. He also said Congress made it clear in its amendment to the law that it wanted to capture all kinds of bribes, kickbacks and undisclosed conflicts of interest.

But that raised more questions from the judges, who said the law did not appear to be that clear. "All you need is misrepresentation," Judge Scalia said, pointing to Judge Breyer's Daily Racing Form example.

After the hearing, Mr. Estrada expressed confidence the law will be struck down. Prosecutors "made big headlines by claiming that Conrad Black was a thief," he told reporters outside the court. "In fact, when the time came to prove that, the government fell flat."

He added that "a core principle of law in this country is that a citizen ought to be able to know, by simply looking at the plain naked test of the law, whether his conduct is in or out. And this law flunks that by a country mile."

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Eric Sussman, who led the prosecution of Lord Black and is now in private practice with a Chicago law firm, Kaye Scholer LLP, said he was surprised by the number of judges who raised questions about the law.

Judge Scalia had already expressed concern about the law earlier this year in an unrelated case and most observers expected him to lead the questioning Tuesday. But it was the other judges who led the way, Mr. Sussman noted.

Whatever the outcome, Mr. Sussman doubted that Lord Black will get out of the Florida jail where he is serving his sentence. The court did not focus on his conviction for obstruction of justice, which carried a 61/2-year sentence. The fraud conviction carried a three-year sentence, which is being served concurrently. So even if the top court were to reverse the fraud conviction, Lord Black would still have to complete the sentence for obstruction of justice.

And even if the court rules in favour on the honest services issue, Lord Black's appeal could fail on other grounds. The former newspaper owner "has a long road to go," Mr. Sussman said.

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