Conrad Black, whose empire once included The Chicago Sun-Times, The Daily Telegraph of London, The Jerusalem Post and small papers across the United States and Canada, was sentenced to six and a half years in prison after he was convicted in 2007 of defrauding investors in Hollinger International. He served more than two years before being freed on bail to pursue what would be partly successful appeals. But federal judge in Chicago determined in June 2011 Black had not served enough time and ordered him back to prison for 13 more months.

Former media baron Conrad Black leaves the U.S Dirksen Courthouse with his wife, Barbara Amiel Black on June 24, 2011. (Antonio Perez/ Chicago Tribune)