Black leaves Federal Court Thursday, Dec. 1, 2005 in Chicago. (Jeff Roberson/Associated Press)

It's been said many times that Conrad Black is one of those larger-than-life characters.

Here we have a rich, opinionated, ruthless, litigious, brilliant and influential aristocrat who, in the space of four years, saw his empire and power unravel amid a slew of criminal charges.

He was born Conrad Moffat Black on Aug. 25, 1944, in Montreal. His father, George Black, was a wealthy brewery executive.

Black's entrepreneurship emerged early, when, as a 14-year-old student at Toronto's elite Upper Canada College, he made $1,400 by selling his classmates stolen exams. It got him expelled.

He shook that off and went on to complete a history degree at Carleton University, a law degree at Laval and an MA from McGill.

In his 20s, Black began buying small Canadian newspapers, and in 1971 he co-founded the Sterling Newspapers Group. The empire had begun.

Crossharbour station in London

In 1978, he became chair of the Argus Corporation, a position he used as a launch-pad to start the Hollinger group. By the 1990s, Hollinger controlled 60 per cent of Canadian newspaper titles, as well as hundreds of dailies in the U.S., England, Australia and Israel.

At one point, he was the publisher of the third-biggest group of newspapers in the world. At its peak in 1999, Hollinger had revenues of more than $2 billion.

Conrad becomes Lord Black of Crossharbour

Life was sweet. That same year, the British government moved to make him Lord Black. This elicited strong opposition from Prime Minister Jean Chrétien who pointed to the Nickle Resolution of 1919, which ruled that foreign governments could not grant honours to Canadians that carry a title or privilege. Black challenged the ruling unsuccessfully in court. Determined to get his title, Black renounced his Canadian citizenship and was officially inducted into the British House of Lords as Lord Black of Crossharbour on Oct. 31, 2001. Crossharbour is the name of a neighbourhood as well as a subway stop on the Docklands light railway, near the Daily Telegraph building — then one of the crown jewels of the Hollinger International empire (now known as the Sun-Times Media Group).

Conrad Black is sworn in as Lord Black of Crossharbour (Oct. 31, 2001)

These were Black's glory days. He and his wife, Barbara Amiel, were known for throwing lavish, must-attend parties at their swank home in London's fashionable Kensington district. He also had mansions in Toronto and Palm Beach, Fla., and a Park Avenue apartment in Manhattan.

Wealthy, powerful, well-connected and the owner of influential newspapers on both sides of the Atlantic, it all made him a frequent subject of media profiles. Canadians and Britons were flooded with articles that profiled his imperial lifestyle, his glamorous wife, his perennial perch among the A-list of the world's Who's Who, his love of suing anyone who crossed him, his merciless business tactics, and his love of a vast vocabulary that seemed to have its roots somewhere in the 19th century.

The fall begins

But by 2003, the stories were taking on quite a different look. And it all began with Hollinger International — the company Black headed as CEO and chairman.

Black owned a chunk of the media empire. But some minority shareholders in the U.S. began to complain that he ran it as if he owned it all. They wondered why Hollinger International's fortunes appeared to be languishing while Black himself appeared to be flourishing.

A special committee of Hollinger's board began to look into the allegations and found what it called evidence of "excessive" fees paid to Black and other executives and demanded repayment.

Federal investigations followed. Authorities keyed in on "non-compete" payments given to Black and fellow executives following Hollinger's sale of newspapers in Canada and the U.S.

The lawsuits fly

In early 2004, Hollinger International removed Black as its chairman and launched a $200-million US lawsuit against him.

The suit accused him of using "sham" accounting to divert corporate assets, and demanded that Black refund all salaries and dividends he collected during the disputed time period. Black countersued.

Black then tried to sell Hollinger's key newspaper titles to Britain's Barclay brothers, but was blocked in court by Hollinger International.

On Aug. 31, 2004, the U.S. Securities and Exchange Commission made public a damning report by the special committee of Hollinger's board — a report that said Black had run Hollinger like a "corporate kleptocracy."

The report said Black and several other executives took hundreds of millions of dollars they weren't entitled to. It accused controlling shareholders and their affiliates of transferring to themselves more than $400 million in the previous seven years. Black sued the special committee for defamation.

In September 2005, former Black associate and longtime friend David Radler pleaded guilty to a single count of mail fraud for his part in a scheme to divert more than $32 million US from Hollinger International. He was given a reduced 29-month jail term in exchange for agreeing to testify for the U.S. government.

Black's Toronto-based holding company, Ravelston, was also charged and subsequently pleaded guilty — over Black's objections — to a single count of mail fraud.

Black's legal problems turn criminal

The legal proceedings against Black turned criminal in November 2005. The U.S. Attorney's Office in Chicago charged Black with eight counts of mail fraud and wire fraud relating to the alleged diversion of millions from Hollinger International. Black pleaded not guilty and was released after posting a $20-million US bond.

In December 2005, prosecutors laid more criminal charges against him, including racketeering, obstruction of justice and money laundering.

Charges of criminal tax evasion followed in 2006.

Black pleaded not guilty to all charges (a money laundering count was later dropped), saying he was clearly entitled to the non-compete payments that came his way. Black referred to the allegations as "monstrous defamations." Even some of his critics acknowledge that Black really believes he's done nothing wrong.

But the fall from grace was swift and brutal. Black soon complained that he and his wife had become persona non grata on the London social scene. His newspaper empire — the Daily Telegraph, the Jerusalem Post, the National Post and 500 others — was no longer his. He had to sell two of his homes and mortgaged another to raise money. His legal fights cost him millions.

Amid all those legal tangles, Black also tried to resurrect his Canadian citizenship. In an op-ed piece that appeared the weekend before his trial began (entitled "I am not afraid"), he ended the story with the observation, "I have never been happier to be Canadian."

4 convictions

Ultimately, his fate resided with a jury in a city where he'd never lived — Chicago. His four-month trial ended in July 2007 with convictions on three counts of mail fraud and one of obstruction of justice. He faced sentencing on Dec. 10, still loudly protesting his innocence and vowing to clear his name on appeal.

On March 3, 2008, Black made the transition from his Palm Beach mansion to a small cell at the Coleman prison complex in central Florida, where he began serving his 6½-year term.

Black got his chance to appeal on May 18, 2009, when the U.S. Supreme Court agreed to review the case.

The following month, U.S. Supreme Court Justice Paul Stevens denied Black's request for bail. He applied again while he was appealing his fraud convictions.

When the case was heard in the U.S. Supreme Court on Dec. 8, 2009, judges asked prosecutors tough questions about Black's conviction. The grilling was taken as an encouraging sign for the jailed media baron as he tried to reclaim his freedom.

On June 24, 2010, the U.S. Supreme Court set aside three fraud convictions against Black, and sent the case back to a lower court.

About two weeks later, Black again applied for bail, this time with the 7th Circuit Court of Appeals in Chicago. Bail was eventually granted, and on July 21, he left the Florida jail where he had been incarcerated for 870 days.

He was released on a $2-million bond, but his bid to return to Canada was denied when U.S. District Court Judge Amy St. Eve said that as a condition of his bail, he could not leave the U.S.

Partial victory

Black's lawyers then asked a federal appeals court judge on Sept. 29, 2010, to throw out the 2007 convictions on three counts of fraud and one count of obstruction of justice. He won a partial victory when the court threw out two of the fraud convictions.

But the court upheld one fraud conviction and the conviction for obstruction of justice. Prosecutors later decided not to retry Black on the cases that were overturned.

On Dec. 17, 2010, in the federal appeals court in Chicago, Black lost the appeal of the two remaining convictions. The case was back before the U.S. Supreme Court the following month when lawyers for the former media baron asked it to hear the appeal of those convictions.

The court ultimately refused to hear that appeal. Black, who sold his Florida mansion and moved to New York, was to be sentenced — again by St. Eve — in a Chicago courtroom on June 24, 2011, on the outstanding convictions.

Prosecutors said Black should be returned to jail, and cited his lack of remorse. Affidavits filed by two prison workers also allege Black shirked tutorial duties while in jail and gathered an entourage of inmates who acted like servants to him.

For his part, Black soundly rejected the claims by the two prison workers that he was not a model inmate. His lawyer filed documents ahead of sentencing touting Black's contributions to the community during his time at Coleman, and his continued support of its students after he was released last year.

The sentencing will, in effect, be a resentencing since the convictions were included in Black's original 6½-year sentence in December 2007, for which he served two years.

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