Radler began talking to authorities in 2004

David Radler, whose co-operation with U.S. prosecutors may have helped launch yesterday's charges against his old friend Conrad Black, first offered help in the case almost a year ago, sources say.

Lawyers with knowledge of the situation say documents show Mr. Radler has been talking to law enforcement authorities about co-operating with them since the end of 2004.

It was only when the indictment against Mr. Radler was filed in August that it became publicly known that he had signed a deal to plead guilty to charges of fraud and help with further investigations.

This issue will likely be raised in the defence of Lord Black, Jack Boultbee and Peter Atkinson, who were added yesterday to the list of those charged with criminal fraud. At the end of 2004, the three, along with Mr. Radler, had been part of a joint defence agreement, and under that arrangement none were supposed to talk individually to prosecutors without the knowledge of the others, sources say.

Mr. Radler, who lives in Vancouver, pleaded guilty in September to charges that he helped divert $32-million (U.S.) from the company. He is next expected back in the Chicago court in February.

If he co-operates to the satisfaction of prosecutors, Mr. Radler will get a reduced sentence of 29 months in jail, and a $250,000 fine. If he does not meet his end of the bargain, he could face as much as five years in jail.

Legal experts said yesterday that Mr. Radler has undoubtedly been helpful to the prosecutors already, and his role will continue right through to Lord Black's trial.

Kirby Behre, a Washington lawyer who is a former federal prosecutor, said it is typical for a prosecutor to try to find a co-operative defendant who is close to the central figure in a case.

It is a little more unusual to get someone like Mr. Radler, who has been close to Lord Black for almost four decades, to testify against an old friend. That creates a "soap opera situation," Mr. Behre said.

Mr. Radler could end up on the witness stand of a Chicago court, face to face with Lord Black and offering evidence that could potentially put him in jail for many years.

That's a long way, physically and emotionally, from Montreal in the mid-1960s, where Mr. Radler first met Lord Black and his colleague Peter White through their connections to the Union Nationale party.

The three young men bought the Sherbrooke Record newspaper together for $18,000 (Canadian), the start of a media empire that at one point spanned the world.

The arc of their business life since then has been legendary. Together the three acquired a chain of small newspapers in British Columbia, later adding the Chicago Sun-Times, The London Telegraph, The Jerusalem Post, media assets in Australia and hundreds of papers in the United States and Canada.

Along the way Mr. Radler developed a reputation of a razor-sharp hatchet man, cutting costs and workers from news rooms in the quest for profitability. But he also garnered admiration from some of his employees, who say he was a highly astute manager who interfered less than many other bosses.

He confined his work primarily to the North American papers, running them from an office in Chicago. He kept his private life private, while Lord Black basked in the limelight.

Mr. Radler "put everything together" after Lord Black "did the creative flair stuff," said Toronto businessman Hal Jackman, who twice served on the Hollinger board.

But the relationship deteriorated sharply over the past few years, as scandal swirled about the empire.

One colleague, who attended board meetings with the two over the past two years, said Mr. Radler was increasingly distracted from day-to-day issues. While Lord Black "carried on with great soliloquies, the best you'd get out of David was one-word answers." The director said Lord Black appeared to be "trying to extend a hand to him; trying to keep him inside the tent" -- an effort that has apparently failed.