CHICAGO - David Radler's practical side may have landed him a reputation as a penny-pinching tattler, but it's also allowed Conrad Black's right-hand man to side-step a lengthy jail sentence and begin rebuilding part of the empire he has lost.

"Radler is someone who's just saying: `What do I have to do to survive?' and Black looks at this as his ultimate battle, and he will somehow reverse the situation and vanquish his foes,'' said George Tombs, a biographer and historian whose most recent book, "Robber Baron: Lord Black of Crossharbour,'' discusses Black's conviction for fraud and obstruction of justice.

"I don't believe Radler's motivation is to be liked,'' Tombs said. "Even though Conrad Black has been a bully and is full of bluster and is trying to get attention, deep down he wants to be admired.''

Since being convicted in July, Black has remained in the spotlight, professing his innocence, vowing to be vindicated on appeal and dismissing the U.S. government lawyers as his "persecutors.'' He was sentenced to six and a half years in jail last week.

Radler, former president at Hollinger International, pleaded guilty to one count of fraud and agreed to testify against Black and three other former executives in exchange for a 29-month sentence and a $250,000 fine. He will be sentenced in Chicago Monday for his role in a large shareholder fraud.

Radler spent eight days on the witness stand in Chicago during Black's trial -- a large portion of which involved being called a liar by defence lawyers and accused of implicating Black only to secure his "sweetheart deal'' with prosecutors.

But while Black was busy trying to shape the public perception of the trial and taking shots at his former friend, Radler was settling debts and positioning himself for the future.

Three months before the trial started, he founded a private company, Rhode Island Suburban Newspapers, headed by his daughter Melanie and long-time colleague Roland McBride -- also an executive at Horizon Publications Inc.

The Delaware-incorporated company, also called RISN Operations Inc., operates four dailies and five weekly newspapers. It's the same type of company that Black and Radler made millions off after beginning their partnership in 1969, with the purchase of the Sherbrooke Record.

"This is what they (Black and Radler) did in Sherbrooke,'' said David Spencer, a professor of information and media studies at the University of Western Ontario.

"They bought an English-language newspaper in a town that was quickly losing its English -language character.  But they made it work by being very judicious about respecting the bottom line.''

That respect for the bottom line was typically enforced by Radler, whose frugality has been highlighted throughout the years by those who worked with him.

Spencer said he once met an obituary writer for London Daily Telegraph who told him Radler's greatest contribution to that publication was that "he made the office more spacious ... by firing a third of the people who work here.''

But while friends content in court filings that Radler "always has shied away from the limelight,'' they say he's not the treacherous germophobe who former employees say rationed pencils and rolls of toilet paper.

"David has always demonstrated concern for the employees that are impacted by changing market conditions,'' McBride said in a letter to the court ahead of Radler's sentencing.

"David's success within the newspaper industry ... has not been at the expense of those he employed.''

Terri Leifeste, a long-time Hollinger employee and publisher for Southern Rhode Island Newspapers, said in her letter that Radler "want(s) his employees to have the same happy family life that he enjoy(s),'' while Barry Mechanic, publisher of the Call of Woonsocket -- a RISN newspaper, calls Radler's advice "on target.''

Spencer said he doubts Radler would, in future, employ the same cost-cutting tactics he did at Hollinger because he just won't have the same kind of latitude.

"If he really is smart about this whole thing, once he serves his time he should have lunch with a guy called David Black (CEO of Black Press Group),'' he said.

"Here's a guy who took a lot of small-town newspapers, weeklies, dailies, some on the margins some making a little bit of extra money, and turned it into a mini-empire that's doing exceptionally well.''

Radler also settled lawsuits with Sun-Times Media Group, formerly known as Hollinger International, and paid back US$63.4 million just before the trial started. To date, Radler and the companies he's been involved with have paid back about US$72 million to Sun-Times.

On Monday, Radler will face the final stage of his Chicago tribulations, when the judge who last week sentenced his colleagues is asked to approve his plea bargain with prosecutors.

Under that agreement, Radler testified that Black was the mastermind behind a plan to pocket millions of dollars in non-competition payments that prosecutors said belonged to shareholders.

While observers expect Judge Amy St. Eve to uphold the deal, some say the judge may have some harsh words for Radler, who she admonished several time while on the witness stand for being an evasive witness.

"If she wasn't going to accept it she would have indicated that by now,'' said Peter Henning, a law professor at Wayne State University and former U.S. Securities and Exchange Commission lawyer.

"She can yell and scream at him ... (but) aside from that ... I would expect that she would give him a reporting date, like with Black and the others.''