Former Hollinger boss David Radler has agreed to a 29-month jail term and a fine of $250,000 US.

On Tuesday, he pleaded guilty in a Chicago court to one count of mail fraud.

Radler, 63, former chief operating officer of Hollinger International and a former associate of Conrad Black, was accused of taking part in a scheme to divert more than $32 million from the newspaper holding company.

It was expected that Radler would plead guilty -- possibly in exchange for testimony against Black.

Radler, holding company Ravelston Corp., and former Hollinger in-house lawyer Mark Kipnis, were each charged with five counts of mail fraud and two of wire fraud.

The indictment alleged that Radler, Black's former right-hand man, supervised negotiations of newspaper sales through which he and other Hollinger managers pocketed millions of dollars in fees that should have gone to the company.

Each count carried a maximum penalty of five years in prison, and a $250,000 fine.

Black has not been charged in the case.

In many recent cases U.S. prosecutors have favoured the strategy of having a second-or third-in-command testify against the top boss.

Radler had already indicated he would testify in the Chicago case, which has not yet named Black in any of its accusations.

Radler, Black and the other top two executives of Hollinger, were employed by Ravelston Corp., which had a contract with Hollinger to provide management services.

Executives and directors of Hollinger held 98.5 per cent of the equity in privately-held Ravelston.

"It was part of the scheme that Ravelston and its agents, including Radler and others, repeatedly abused their authority and fiduciary obligations as managers of International in order to fraudulently benefit themselves at the expense of International and its public shareholders," the indictment said.

In addition, it alleges the former media bosses disguised bonus payments as non-competition fees to "defraud the Canadian tax authorities."

Non-compete fees are paid by the buyers of newspapers to ensure the sellers don't set up a competing newspaper in the same market.

Non-compete fees are not taxable under Canadian tax law, which applied to Radler, who lives in Vancouver but often stayed in a Chicago apartment paid for by Hollinger.

Convictions of high-profile white-collar criminals have been mounting in the United States, as regulators try to reassure investors and wipe up the image of corporate America that was tarnished by major frauds including Enron Corp.'s collapse in 2001.

Former WorldCom CEO Bernard Ebbers was sentenced to 25 years in prison for his role in an $11 billion accounting fraud.

Tyco International Ltd.'s former chief, Dennis Kozlowski, and CFO, Mark Swartz, were convicted in June on 22 of 23 counts of grand larceny, conspiracy, securities fraud and falsifying business records.

Kozlowski and Swartz were both sentenced to 8 1/3 to 25 years in prison Monday and ordered to pay $134 million in restitution.

In addition, Kozlowski was fined $70 million and Swartz $35 million.

And home diva Martha Stewart's well-known stock trades landed her in prison for five months, with an additional five months of home confinement.

Enron's founder, Kenneth Lay, is scheduled to stand trial in January on fraud and conspiracy charges.

The company's former CFO, Andrew Fastow, has already agreed to serve the maximum 10-year sentence for his part in the conspiracy, and to testify against his former bosses.