Conrad Black's trial, which starts Wednesday in a U.S. federal court in Chicago, will be one of the most-watched legal events in years.

"It's going to be the most exciting trial in Canadian history," predicted Peter C. Newman, author of "The Establishment Man," an early look at Black's business career.

The stakes are high: If the larger-than-life, Canadian-born former newspaper tycoon is convicted, he'll likely spend the rest of his natural life in jail.

If acquitted, he's vowed to sue those who have wronged him. However, he also has dozens of civil actions hanging over his head. Even if he's acquitted on criminal charges, the 62-year-old may spend many years in a civil courtroom fighting his adversaries.

All of this turmoil stems from Black's tenure as CEO of Hollinger International, the company under which he operated his once-vast newspaper empire (he held a majority stake in Hollinger International through his holding company, Hollinger Inc.).

Black was born to an establishment Toronto family, but carved a business career of his own. "He took the $7 million he inherited from his parents and spun it into $4 billion worth of company assets," Newman told CTV Newsnet.

Black and his long-time partner David Radler started in newspapers with the 1969 purchase of the Sherbrooke Record.

Black eventually built up one of the world's major newspaper empires through ruthless cost control and intelligent investment of the profits.

At his peak, he controlled titles like the Chicago Sun-Times, The Daily Telegraph, Jerusalem Post and a string of major metro newspapers in Canada -- along with hundreds of smaller papers in Canada and the United States.

In 1998, he launched his flagship, the National Post -- a daily newspaper with a distinctly conservative slant.

During this period, Black and his glamorous second wife, journalist Barbara Amiel, lived a jet-setting life that many billionaires would envy.

They had homes in Toronto, London, New York and Palm Beach, Florida. Former U.S. secretary of state Henry Kissinger and former British prime minister Margaret Thatcher were both friends and members of a special board of advisers to Hollinger International.

Black, while prosperous, wasn't stratospherically wealthy. (Amiel told Vogue magazine in 2002 that "I have an extravagance that knows no bounds" - a remark she later said was meant to be self-deprecating). And his business problems were beginning to mount.

Collapse of an empire

Black's empire started to shrink in 2000. He sold 13 major newspapers, 126 smaller ones and some Internet properties to CanWest Global Communications Corp. for $3.2 billion.

More sales would come, although in Oct. 30, 2001, Black achieved a long-time personal goal by being named to the British House of Lords -- earning the right to call himself Lord Black of Crossharbour.

That honour came with a price: He had to give up his Canadian citizenship after then-prime minister Jean Chretien first blocked him from the title.

Restive shareholders were a bigger problem in this period.

By 2003, Black was in trouble, with an investigation launched into US$74 million paid in "non-compete" fees.

These fees were monies paid to ensure Black wouldn't start newspapers in markets where he had just sold Hollinger International papers.

In November of that year, Black stepped down as CEO of Hollinger International, a move that was followed by a series of corporate and legal skirmishes.

In August 2004, a special committee of Hollinger International claimed Black and others took hundreds of millions of dollars to which they weren't entitled.

The U.S. Securities and Exchange Commission made the report public but Black blasted the document as being full of inaccuracies.

Two months later, the SEC slapped a civil lawsuit against Black, Radler and Hollinger Inc. The securities regulator accused them of diverting funds from Hollinger International.

In March 2005, those civil troubles turned criminal. U.S. federal prosecutors confirmed that Black, Radler and Hollinger Inc. were the subjects of a criminal investigation.

About one month later, Black and Radler resigned from Ravelston, which was a key corporate component in the management of Black's now-crumbling empire. That company filed for bankruptcy, saying its liabilities had outstripped its assets. The company said it was also starved for cash because it was no longer collecting management fees from Hollinger Inc. and Hollinger International.

Criminal charges

On Sept. 20, 2005, Radler would plead guilty to charges of wire fraud stemming from an alleged plan to divert US$32 million from Hollinger International. He was sentenced to 29 months in jail and fined US$250,000, contingent on his co-operating.

Two months later, prosecutors filed eight charges of mail fraud and wire fraud against Black. Four more charges would come later: Racketeering, money laundering and obstruction of justice.

Prosecutors say the non-compete money should have gone to Hollinger shareholders and not into the pockets of Black and other executives.

Former Hollinger executives Jack Boultbee, Peter Atkinson and Mark Kipnis also face mail or wire fraud charges. All have pleaded not guilty.

Estimates of Black's sentence, if he is convicted on all counts, range from 95 to 116 years in prison.

In the weeks leading up to the trial, the famously pugnacious Black filed a US$11 million lawsuit against author Tom Bower over his book "Conrad and Lady Black: Dancing on the Edge."

Among other claims, Black alleged the book portrays his wife as "grasping, hectoring, slatternly, extravagant, shrill and a harridan."

Black has mounted a relentless campaign proclaiming his innocence, even having "Conrad Will Win!" T-shirts printed up for his friends.

He recently sat down to dinner with Globe and Mail columnist Patricia Best at Toronto's exclusive Scaramouche restaurant.

"He's always the same person. His appearance is that of a man who is confident, who is relaxed, who seems happy," she told CTV's Question Period. "He is in fine form. He is convinced of his innocence, and if you give him half a chance, he'll tell you all about it."

Will Black tell his own story where it counts -- on the witness stand?

"That's a big question, and he says he doesn't know," Best said.

"It is up to him. It's his trial, and it's his liberty at stake. So the decision at the end is his. However, his lawyers will obviously have a lot to say about that. But if they're opposed to it and he's for it, they can't stop him."

One of Black's defence lawyers, Eddie Greenspan, said he is looking for a jury that will give his client a fair trial and one that will ultimately acquit him.

The defence team hasn't decided yet if Black or his wife will take the stand, Greenspan told CTV's Canada AM on Tuesday morning.

"At the end of the prosecutions' case, we will sit down and assess the weaknesses and strengths of the prosecution's case and decide whether it's necessary for Conrad Black to testify or not, and whether or not it's necessary for Barbara Amiel Black to testify or not," Greenspan said.