Looking at ease, the former head of the company that owned the Chicago Sun-Times entered the same courtroom where he was convicted in 2007 of fraud and obstruction of justice.
But, this month, the law under which the bulk of the charges against him were drawn up -- the "honest services" law -- was deemed too vague by the United States Supreme Court. And Black appealed his conviction. But he can't go home to Canada just yet.
It was a plea Black's lawyer asked Judge Amy St. Eve to grant as black awaits the ruling on his appeal. The judge, however, demanded more information on Black's finances beyond that offered in an affidavit given to the court.
Black will be back in court in Chicago August 16 with a document he hopes the judge will accept. St. Eve said there is a lot of uncertainty about Black's finances.
Thursday night, Black and his wife, Canadian newspaper columnist Barbara Amiel, headed into Chicago's Four Seasons Hotel. Black made it clear he thinks he is in a war with the U.S. government.
"We're in a war and we're winning," Black said Thursday night.
Black answered "Yes, your honor" several times to the judge when he was asked if he understood the terms of his freedom. He must remain in the continental United States, and he cannot apply for a new passport to replace his expired one.
Black is free on $2 million bail posted by a New York businessman who is a longtime friend, and he cannot pledge his former Florida mansion as security because it is now owned by a Connecticut investment firm and has been put up for sale.
"He has a very delicate balancing act right now, because he has a bunch of civil litigants that are very interested in where his assets are," said Hugh Totten.
Totten is a corporate litigation lawyer who has followed the Black trial closely. He thinks that Black will get his wish to return to Canada eventually.
"His victory came earlier this week when the 7th Circuit issued its bail order, which I think is fairly interpreted to mean that appellate courts don't order bail for people that are gonna go back to jail," Totten said.
Black will be back in court Monday, August 16. The U.S. prosecutor indicated that it is likely the 7th U.S. Circuit by that time will have heard Black's appeal of his conviction.