The man accused of running Hollinger International as a personal fiefdom denied eight counts of fraud, each of which carries a maximum penalty of five years in prison and big fines, when he made his first court appearance before a judge in Chicago.
Mr Black's conglomerate at one stage included the Daily Telegraph newspaper in Britain, the Jerusalem Post, the Chicago Sun-Times and hundreds of regional papers around the world.
The 11-count indictment handed down Nov 17 described two complex schemes in which Mr Black and his associates diverted funds from the sale of hundreds of newspapers in the United States and Canada by inserting non-competition agreement payments into the deals.
He is accused of lying to shareholders and his board of directors in order to perpetrate the fraud.
Mr Black was also charged with fraudulently misusing corporate perks by throwing a lavish birthday party for his wife and using a corporate jet to take a vacation to Bora Bora in French Polynesia.
The indictment calls for the forfeiture of nearly US$100 million in assets, including Mr Black's Palm Beach, Florida home.
Also named in the indictment were Hollinger International's former chief financial officer John Boultbee, 62, of Toronto; Hollinger Inc's former vice president and general counsel Peter Atkinson, 58, also of Toronto; Hollinger International vice president and chief counsel Mark Kipnis, 58, of Northbrook, Illinois; and the Ravelston Corporation.
Mr Atkinson also pleaded not guilty. Mr Boultbee failed to appear in court to face fraud charges on Wednesday, a move which could lead to extradition proceedings, a prosecutor said.