Former Hollinger International insider David Radler pleaded guilty to one count of mail fraud Tuesday in a 32-page plea agreement in Chicago. Radler, 63, was president and chief operating officer of Hollinger International Inc. and a one-time lieutenant to newspaper baron Conrad Black.

Radler was indicted Aug. 18 on five counts of mail fraud and two counts of wire fraud. The former publisher of the Chicago Sun-Times was accused of participating in a scheme to divert more than $32 million (all figures U.S.) of "non-compete fees" from the newspaper holding company into his and other managers' pockets.

David Radler in 2001 (CP Photo)

Radler -- who remains free on bond -- is cooperating with prosecutors in the ongoing investigation. His sentencing was postponed.

Radler could receive five years in prison and a $250,000 fine. But -- according to the plea agreement -- federal prosecutors will recommend 29 months in prison and a $250,000 fine if Radler provides his full cooperation.

Radler's attorney Anton Valukas said: "This is the first step in making amends for what has taken place." Valukas added that Radler feels "sorry and saddened for the pain he has caused."

Ravelston Corp., Black's insolvent Toronto holding company, and former company lawyer Mark Kipnis have also been charged.

Kipnis, 58, who was the top in-house lawyer for Hollinger International, pleaded not guilty last month. He is free on a $250,000 bond.

Kipnis is accused of participating in the scheme and not telling Hollinger International's audit committee about the illegal payments. The indictment says Kipnis participated in documenting and closing each deal, the business terms of which were supervised by Radler.

Black, who controlled the company's media assets through Ravelston and the Toronto-based holding company, Hollinger Inc., has not been charged.

Hollinger International's independent directors have been investigating the company's accounts and are engaged in major litigation against the former chairman and CEO, and his associates. Disputes, investigations and legal proceedings with former executives and directors cost $22.4 million in the first half of 2005, in addition to $60.1 million last year.

Black and Radler face numerous civil suits accusing them of cheating investors.