Still in his early 20s, the young Conrad Black gets into the newspaper business on a small scale at the Eastern Townships Advertiser, bought for a dollar by friend and future Hollinger principal Peter White. A French language weekly in Cowansville is added and gradually the papers begin to turn a small profit.

They buy their first real newspaper, the Sherbrooke Daily Record, and the third partner, David Radler, joins and is eventually credited with much of the business savvy that made Hollinger profitable for so many years.

The "chain" begins to grow as Sterling Newspapers is founded and in all, over 10 years, they snap up 22 tiny papers. Before they buy, Black and his partners visit each in the evening and count the desks. Twenty desks equal 20 employees. This way they can calculate how many they can sack once they make the purchase.

The corporate structure begins to take shape as Hollinger is spun off from Argus, part of the overall Black family financial empire, and the next year Argus sells Standard Broadcasting to Hollinger.

Hollinger purchases an interest in the Daily Telegraph group in Britain and the next year gets control of the Daily Telegraph.

 Hollinger dumps Standard Broadcasting.

Hollinger increases its international holdings with the addition of the Spectator magazine (U.K.) and the Jerusalem Post (Israel).

Hollinger buys Torstar Corp.’s almost one-quarter interest in the Southam Newspaper Group.

Hollinger sells slightly less than 10 per cent of its controlling stake in the Telegraph Group, retaining a majority 57-per-cent interest, and buys the Chicago Sun-Times Group.

Hollinger picks up a dozen daily Canadian newspapers and seven weeklies from Canadian Newspapers Ltd., owned by Ken Thomson, then the Regina Leader-Post and Saskatchewan Star-Phoenix, quickly sacking a large number of staff members to make the papers more profitable.

Hollinger snags six daily newspapers in Atlantic Canada, one more weekly from the Thomson chain, and doubles its shares in Southam to gain control and become the unquestioned dominant player in the Canadian newspaper business.

Hollinger cuts some of its smaller U.S. newspaper holdings, the Hamilton Spectator, Kitchener-Waterloo Record, Guelph Daily Mercury and Cambridge Reporter, but also buys the Gary Post-Tribune in Indiana for US$40 million and the same year launches the National Post in Toronto.

Hollinger buys up the remaining minority interests in Southam Inc. and turns it into a private company.

After 34 years of growth, Black’s Hollinger and Black himself are getting ready to bid goodbye to Canada. Black loses a fight with Prime Minister Jean Chrétien that ends up in court as he tries to gain dual British-Canadian citizenship, which would allow him to accept a peerage in Britain. Hollinger sells most of its Canadian holdings to I.H. Asper’s CanWest Global, although it retains a 50-per-cent interest in the money-losing National Post. Hollinger also sells its last small daily newspapers in the U.S. division.

Hollinger sells some smaller papers that CanWest didn’t buy to Michael Sifton and his Osprey Media Group, then renounces his Canadian citizenship and sells the rest of the National Post to CanWest. Black finally gets his wish and becomes a British Lord, then unloads his stake in the now debt-ridden CanWest, which, all told, has paid about $3.5 billion to Hollinger.

A Hollinger International shareholder storm that has been building for months in the United States unleases its fury on the media baron.

Black is forced to step down as CEO of Hollinger International Inc. after a fuss is raised over allegedly unauthorized "non-compete" fees and management payments he, David Radler and other lieutenants have been receiving for running the much-diminished Hollinger Inc. Radler loses his Chief Operating Officer and President positions at Hollinger International.

Black, who announced when he lost the CEO job that he "still remained in control" of Hollinger International, is still chairman and controls 73 per cent of the company's voting stock.

Hollinger International's only independent directors, who comprise the four-person audit committee, resign after their recommendations presented to the board were refused by chairman Black.

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The board of Toronto-based holding company Hollinger Inc. has rapidly shrunk from 12 members to five as two more directors announce they are jumping ship. The remaining board members include Peter White (who takes over as secretary of the company and serves as co-COO with Radler), Black, Radler, Black's wife Barbara Amiel Black, and Jack Boultbee, who was fired in November from his exec position at Chicago-based operating company Hollinger International.

The company starts a desperate search for new directors. Without any independent directors, it could run afoul of the Canada Business Corporations Act and fail to meet Toronto Stock Exchange requirements.

Black remains as chairman and CEO of Hollinger Inc.

The U.S. Securities and Exchange Commission alleges that certain employees of Hollinger International "falsified" corporate books and records, and hadn't been forthcoming with relevant information about some deals.

Hollinger International declares what some reports describe as "all-out war" on the media baron, announcing a huge legal claim against Black, Radler and Black's holding companies. The suit demands repayment of at least US$200 million in "excessive, unreasonable and unjustifiable" non-compete fees and management payments.

The lawsuit further alleges that unfair transactions "diverted and usurped corporate assets (of Hollinger International)." It claims that Black and Radler "freely used the company's coffers, financed by its public shareholders, to finance their own lifestyles and to support independent pursuits."

Because a special committee of the company's board has not finished its investigation, which is expected to last into the spring, more allegations and claims are expected to push the damages sought far beyond the US$200-million mark.

At a meeting of the company's executive committee later that evening, Black is dumped as chairman.

Black announces that he has made a deal to sell Hollinger Inc. to Press Holdings International Ltd., a private British conglomerate owned by identical twins and billionaires David and Frederick Barclay. The embattled Black says in a statement that "it will be distressing to part from the Telegraph newspapers, the Spectator, the Chicago newspapers and The Jerusalem Post."

Conrad describes Hollinger International's lawsuit as a "spurious complaint" intended to divert attention from his plan to sell Hollinger Inc. (Radler says the lawsuit "lacks any factual or legal basis.")

Days later, Hollinger International sets up a special board committee to examine and possibly block Black's proposed sale of Hollinger Inc., and to itself explore a possible sale of the Telegraph group as well as other major assets of the U.S. operating company.

Conrad Black fires back in his legal battle with Hollinger International, filing an $850-million lawsuit against several of the company's directors in an Ontario court, alleging they defamed him.

A judge prevents media baron Conrad Black from selling control of his Hollinger International media empire, saying Black had seriously breached his duties to the company.

Conrad Black appeals Delaware court decision that blocked his sale of Hollinger International Inc. to two British entrepreneurs.

Regulatory documents reveal Barbara Amiel Black exercised stock options allowing her to purchase 269,000 Hollinger International shares for just over half what the stock was worth on the open market. All the options were exercised one day before Hollinger International advised members of its various stock option plans and the Securities and Exchange Commission that it would suspend such transactions after April 30.

In a radical escalation of its war against founder Conrad Black, Hollinger International Inc. increases its court claim against him and other executives of the newspaper group to US$1.25 billion and accuses them of corruption. Black fires back that the company's latest action "is tabloid journalism masquerading as law."

Hollinger International Inc. paid for personal expenses of Conrad Black and his wife Barbara Amiel, ranging from the cost of refurbishing a 1958 Rolls-Royce to the tip handed to a Bergdorf-Goodman doorman, according to allegations in the latest incendiary lawsuit in the Hollinger saga.

Hollinger International Inc. has reached a settlement with its former director Peter Atkinson, who has returned US$2.8-million in payments he received from the company.

Barbara Amiel is dropped as a columnist for The Daily Telegraph newspaper in London. The Telegraph says Lady Black was axed because she was added as a defendant to Hollinger International's massive lawsuit against Lord Black, his holding companies, and several of his colleagues.

Canada's top securities regulator slaps a trading ban on executives and insiders at Argus, the Conrad Black-controlled holding company with a major stake in Hollinger.

Canada's top securities regulator extends a trading ban on insiders of three firms in Conrad Black's Hollinger newspaper empire because the companies missed deadlines to file financial results. The more than 40 individuals and companies covered by the trading ban include Black and his wife Barbara, as well as such high-profile Hollinger International directors as former U.S. Secretary of State Henry Kissinger and ex-Pentagon adviser Richard Perle.

Hollinger International admits it overstated circulation at the Chicago Sun-Times for years.

Conrad Black's attempt to thwart Hollinger International Inc.'s sale of its marquee Telegraph Group Ltd. rests on his ability to convince a Delaware judge that he and other shareholders have the right to vote on the $1.8-billion sale.

A newspaper publisher who wants to buy the Sherbrooke Record from Conrad Black is trying to force him to sell by challenging whether the Record qualifies as a Canadian newspaper because Black relinquished his citizenship three years ago.

Lord Black vows he will "repossess the company in the autumn" and rails against the "truly evil people" and "fascists" who are attempting to take control of his empire.

U.S. court refuses request from Conrad Black's Hollinger Inc. to stop the sale of Telegraph Group.

Hollinger International sells one of Europe's top-selling newspapers without holding a shareholder vote — another setback for embattled media mogul Conrad Black.

Henry Kissinger and a group of fellow former directors of Hollinger, which was until recently the parent company of The Daily Telegraph, are in US$100-million settlement talks that could spare them legal action over a financial scandal in the media group.

Former Hollinger International Inc. chief operating officer Daniel Colson says he should be dropped from a US$1.25-billion Chicago lawsuit filed against him and other former executives by the company, because he has hardly ever been to Illinois.

Special 513-page report commissioned by Hollinger International is filed with the U.S. Securities and Exchange Commission and released to the public.

Media worldwide have a field day. A sampling of headlines:

Hollinger directors slammed | Australian Financial Review
Report blasts Black for 'looting' Hollinger | CTV - Canada
Hollinger says $400M 'taken' by execs | Washington Times
Media barons 'filched $400m' from Hollinger | Business Day - Johannesburg, SA
Hollinger Board's Report Accuses Black of Running 'Kleptocracy' | CRM Buyer - USA
Probe: Ex-Hollinger CEO Looted Profits | Atlanta Journal Constitution
SEC office to recommend civil charges against Hollinger Inc. | WQAD - Moline, IL
Hollinger faces civil action as executive perks revealed | Media Bulletin - UK
Probe: Ex-Hollinger CEO Looted Profits | Forbes - USA
Shareholders the losers, report charges | Toronto Star
Hollinger says ex-chief victimized the company | Sun-Sentinel.com - Fort Lauderdale, FL
Hollinger Claims Black Took Cash | Ananova - UK
Report: Former J'lem Post publisher mishandled paper's charity fund | Ha'aretz - Israel
Report alleges Hollinger misled on CanWest | The Globe and Mail - Canada

Hollinger's Black Mortgages Toronto Mansion, National Post Says | Bloomberg - USA
Insurers give directors cold comfort | Toronto Star
A circle of power, position, influence and money | Montreal Gazette

Ontario judge orders court-appointed inspector for Hollinger Inc. | Miami Herald
Hollinger non-execs ‘must pay’ | The Times London, UK
Here's the word on how Conrad blew $400 million | Toronto Star
KPMG joins Lord Black in firing line | Financial Director - London, UK

Chicago Sun-Times reports that, even before her husband was thrown out of Hollinger International, Barbara Amiel Black managed to make money on the company.

Five Canadian investors launch a class-action lawsuit against Black, Amiel, Radler and others, seeking at least $4 billion in damages. The suit seeks to recover market losses that may have been caused by controversies involving Black's management and allegations he and associates looted the company.

Globe and Mail takes an in-depth look at the related-party deals:

"As the damning report of the Hollinger International Inc. special committee outlines it, Conrad Black and some of his lieutenants wanted to get their hands on millions of dollars in tax losses sitting on the media company's books back in November, 2001. But Peter Atkinson, one of Lord Black's lieutenants, was clearly worried about the group asking the audit committee to approve another related-party transaction, especially since New York investment firm Tweedy Browne Co. was starting to question the management fees flowing from Hollinger International to the Black group."

Conrad Black files a $1.1-billion defamation lawsuit against a special committee of Hollinger International. The board released a report on Aug. 31, 2004, that accused him of looting the company.

Kelowna Capital News reports that "corporate shenanigans of former owners of this newspaper and the current and former owners of the Kelowna Daily Courier — at times the same owners hidden behind a veil of corporate secrecy only recently revealed to its full extent — helped bring about a shareholder revolt within the Hollinger International shareholder ranks ..."

A U.S. Federal Court judge throws out Hollinger International's US$1.25-billion racketeering lawsuit against Black and other former executives.

Conrad Black resigns as chairman and chief executive of Hollinger Inc.

The U.S. Securities and Exchange Commission lays a civil fraud lawsuit against Conrad Black, Hollinger's former deputy chairman and chief operating officer David Radler, and Hollinger Inc. It accuses Black and Radler of improperly diverting tens of millions of dollars from Hollinger International.

An Ontario Superior Court Judge orders three directors of Hollinger Inc., including Black's wife and the company's chief operating officer, removed from the board of directors immediately.

Black is named Canadian business newsmaker of the year by the Canadian Press and Broadcast News.

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Hollinger Inc. agrees to put a US$47.3-million share of a dividend being paid out by Hollinger International into an escrow account. The money will remain frozen until the SEC actions against Hollinger and Black are resolved.

Black drops his $2.1-million defamation lawsuit against Toronto Life. The magazine printed an apology in its February issue for a satirical story in its July 2004 issue depicting Black as "so irredeemably evil that he should be consigned to Hell."

The Ontario Securities Commission files notice that it intends to launch proceedings against Black, Hollinger Inc., and three former associates for alleged violations of securities laws. In the statement of allegations, the OSC accuses Black of "egregious conduct."

U.S. federal prosecutors confirm that Black, top lieutenant David Radler and Hollinger Inc. are the subject of a criminal investigation. The government tipped its hand when if filed court papers asking to intervene in the SEC lawsuit against Black, Radler and Hollinger.

Black and his longtime business partner Radler resign as officers and directors of Ravelston Corp., the private holding company through which Black controlled his crumbling media empire. The announcement was made in Ontario Superior Court as Ravelston applied for bankruptcy protection. The company says it has run out of money because it is no longer receiving management fees from Hollinger Inc. and Hollinger International.

Conrad Black, his chauffeur, and his personal assistant are caught on security video removing 12 boxes of files from Hollinger Inc.'s Toronto headquarters. The removal occurs despite an Ontario court order that bars Black from taking documents from the building. Black's lawyer says the boxes contain "personal" items that aren't covered by the court order.

Radler pleads guilty to mail fraud in connection with plan to divert US$32 million from Hollinger International. Receives reduced sentence of 29 months in return for promise of co-operation.

U.S. Attorney's Office in Chicago seizes US$9 million from sale of Conrad Black's New York apartment, saying proceeds were accumulated as part of an alleged fraud scheme.

Black sues the U.S. government, claiming the Federal Bureau of Investigation improperly seized almost US$9 million of his money.

The U.S. Attorney's Office in Chicago charges Conrad Black with eight counts of mail fraud and wire fraud. The indictment alleges Black and three other former Hollinger International executives pocketed millions of dollars from the company's sale of newspaper assets to CanWest Global in 2000.

Black fails to show up at a Chicago courthouse to face fraud charges. His lawyer assures the U.S. Attorney's Office that he will come on Nov. 30. American officials initially said they would start extradition proceedings against Black if he didn't appear in court.

Conrad Black appears in a Chicago courtroom and pleads not guilty to fraud charges in connection with the alleged looting of $80 million from Hollinger International Inc., the newspaper empire he once controlled. The plea was entered on Black's behalf by his U.S. lawyer Edward Genson. Black is facing a total of eight counts of fraud.

Black is released on $20 million bail. He is ordered to live only in Canada, Chicago, or Florida. His travel is restricted to between Canada and the United States. He waives his right to contest any extradition attempt should he not turn up for trial later.

John Boultbee – the accountant who served as chief financial officer of Conrad Black's publishing empire – pleads not guilty in a Chicago courtroom, to fraud charges involving the sale of hundreds of Canadian newspapers. He is ordered released after posting bail of $1.5 million and waiving his right to contest any future extradition from Canada. Boultbee is facing eight counts of mail and wire fraud.

Conrad Black faces four new charges, including racketeering, money laundering and obstruction of justice. The last charge relates to the removal of boxes of documents from Hollinger's offices in May 2005. If convicted of all 12 charges he now faces, he could get 95 years.

A U.S. federal court judge sets Mar. 5, 2007 as the date for Conrad Black's trial on charges of fraud, racketeering and obstruction of justice to open.

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