Lawyer Mark Kipnis, former lieutenant to ex-media magnate Lord Conrad Black, has denied fraudulently diverting up to $32 million (€26m; £17.8m) from Chicago Sun-Times publishing firm Hollinger International.
Kipnis, appearing at Chicago district court, pleaded not guilty to five counts of mail fraud and two counts of wire fraud. He was freed on a $250k personal recognizance bond.
The same charges have been brought against the newspaper's former publisher David Radler and Ravelston Corporation, a holding company once controlled by Radler and Black. The latter has not yet been indicted of wrongdoing.
Radler, who resigned from H-Intl in 2003 together with Black, is co-operating with the authorities and is due to appear in court next month to plead guilty.
Ravelston's arraignment was also postponed until September after the court was told the company had not yet decided how it will respond to the charges.
The indictment alleges Radler, Kipnis and Ravelston diverted the money from H-Intl through a series of secret deals by disguising it as non-compete fees connected to the sale of newspaper publishing groups.
Data sourced from Wall Street Journal Online; additional content by WARC staff