2012

May 4: Conrad Black arrives in Toronto, a few hours after his release from a Florida prison.

April 18: In a unanimous decision, the Supreme Court of Canada rules, to Black's delight, that defamation claims he brought in 2004 and 2005 against Hollinger Inc. board members and their adviser, Richard Breeden, can proceed in Ontario.

March 20: Black applies for temporary residence in Canada. On May 1, it's made public that the federal government had approved Black's application, good for one year.

2011

Sept. 6: Black returns to prison to serve out the rest of his sentence for fraud and obstruction of justice after being released from jail for about 13 months while the courts reviewed some of his convictions. He will serve out the new sentence in the Federal Correctional Institute about 50 kilometres from Miami.

Aug. 31: A Matter of Principle, Conrad Black's memoirs of his trial and prison life is published.

June 24: Black is resentenced to 42 months in prison for his two remaining convictions— for fraud and obstruction of justice, respectively. The new sentencing was ordered after the U.S. Supreme Court struck down some of Black's initial convictions. Black will receive credit for the 29 months of his original 6½-year sentence he has already served .

May 31: The U.S. Supreme Court refuses to hear Black's appeal of his two remaining convictions.

Feb. 17: Black's lawyers ask the U.S. Supreme Court to hear the appeal of his remaining convictions.

2010

Dec. 17: Black loses the appeals of his convictions for fraud and obstruction of justice in a federal appeals court in Chicago.

Oct. 29: Black wins a partial victory as a U.S. appeals court throws out two of his fraud convictions. However, the court upholds one fraud conviction and another for obstruction of justice. Prosecutors later decide not to retry Black on the cases that were overturned.

Sept. 29: Black's lawyers ask a federal appeals court judge to throw out the former media mogul's 2007 convictions — for three counts of fraud and one count of obstruction of justice.

Aug. 13: The Ontario Court of Appeal rejects a motion by current and former directors of Hollinger International to throw out Black's libel suits against them. Black's multimillion-dollar defamation actions can now proceed. 

Aug. 6: Black drops his request to be allowed to return to Canada while out on bail, according to media reports.

July 23: U.S. District Court Judge Amy St. Eve denies Black's request to return to Canada under the conditions of his bail. St. Eve orders Black to return to court on Aug. 16 with more financial details, as she deemed the financial affidavit he had provided to be insufficient. Black must remain in the United States in the meantime.

July 21: Black is released from the Coleman Federal Correctional Complex in Florida, where he has been incarcerated for the past 870 days. Black is released on a $2-million US bond, following a bail hearing in which U.S. District Court Judge Amy St. Eve says Black cannot leave the United States as a condition of his bail.

July 19: Black is granted bail while he appeals his conviction for fraud. The terms are to be set by the judge that oversaw his original trial.

July 7: Black applies for bail with the 7th Circuit Court of Appeals in Chicago.

June 24: The U.S. Supreme Court sets aside three fraud convictions against Black and sends his case back to a lower court.

March 25: Black no longer owns title to the Florida mansion he bought in 1997, the Globe and Mail reports.

2009

Dec. 8: U.S. Supreme Court judges asked prosecutors a slew of tough questions about the conviction of Black, an encouraging sign for the jailed media baron trying to reclaim his freedom.

June 22: Black makes a second bail request while he appeals his fraud convictions.

June 11: U.S. Supreme Court Justice John Paul Stevens denies Black's request for bail. Stevens turns down another request for bail on Aug. 10.

May 18: The U.S. Supreme Court says it will review Black's fraud convictions. The justices will hear arguments from Black's legal team later this year.

Jan. 9: Black asks the U.S. Supreme Court to hear his case in a last-ditch effort to overturn his convictions. Black's appeal for clemency from departing President George W. Bush won't be granted.

2008

June 25: A three-judge panel of the U.S. Court of Appeals upholds Conrad Black's 2007 convictions  — on three counts of fraud and one count of obstruction of justice.

June 5: Lawyers for Black face tough questioning from a panel of three appeals court judges during a short hearing in Chicago.

March 14: Black's lawyers file an appeal of his convictions, arguing that U.S. prosecutors failed to prove their case against the former press baron.

March 3: Black reports to a prison complex in Coleman, Fla., to begin serving his 78-month sentence.

Feb. 28: Black loses his attempt to stay free on bond until his appeal is heard and is ordered to report to prison on March 3. The U.S. Court of Appeals does, however, agree to let Black's two co-defendants remain out of jail while they appeal their fraud sentences.

Feb. 21: Black asks the U.S. Court of Appeals for permission to remain on bail until his appeal is heard. His lawyers argue that a short delay of his surrender date would not "undermine the goals of the justice system."

2007

Dec. 10: Black is sentenced to 6½ years in prison, is fined $125,000 US and ordered to pay $6.1 million US in restitution. He must report to a minimum-security federal facility in Florida on March 3 and will remain free until then.

Dec. 5: In emails to CBC and other media organizations, Black says he'll cope with jail, "if it comes to that," but vows to keep up the fight to clear his name. A prison term, he said, would "only compound the injustice of this entire vendetta."

Nov. 5: Black's bid for a new trial is rejected. "The government introduced more than enough evidence to support each defendant's conviction on the mail fraud counts and defendant Black's obstruction of justice conviction," Judge Amy St. Eve rules.

Oct. 23: Richard M. Nixon: A Life in Full, by Conrad Black is published.

July 13: After 15 weeks of testimony, more than 40 witnesses and about 700 documents, the jury deliberates for 12 days before convicting Black of one count of obstruction of justice and three counts of mail fraud. His lawyers quickly vow to appeal. Black's co-accused are each found guilty of three counts of mail fraud. Meanwhile, in London, the Conservative Party announces that Black will no longer site as a Conservative in the House of Lords. "In the light of this verdict the Conservative whip will be withdrawn from Lord Black," the party says in a statement.

March 14: Jury selection begins in Chicago. The trial of Black and three co-accused is expected to take three months. Some 300 journalists from the U.S., Canada, Britain and Europe are accredited to cover the proceedings.

March 5: Ravelston Corp., a private holding company used by Conrad Black to control the Hollinger newspaper empire, pleads guilty to a single count of mail fraud and agrees to pay a fine of $7 million US. Black's lawyers had tried to block the Ravelston plea.

Feb. 19: Black files an $11-million libel suit against British author Tom Bower, whose unflattering book, Conrad & Lady Black: Dancing on the Edge, outraged the couple.

Jan. 23: Judge Amy St. Eve rules that Black and his three co-defendants will be tried together. She denies a motion by the lesser-known co-defendants to be tried apart from Black. St. Eve said she would address their concerns through "appropriate jury instructions."

2006

Sept. 25: Black tells TVOntario that he is working to regain the Canadian citizenship he renounced in 2001 to sit in the British House of Lords. "I always said that I would take my citizenship back, and if it wasn't for all these legal problems, I would have done it by now," he tells interviewer Steve Paikin.

Aug. 18: Black and three co-accused are charged with tax evasion for allegedly causing Hollinger International to under-report corporate income of $13 million US to $16 million US in 1999 and 2000. The next month, Black pleads not guilty.

'I always said that I would take my citizenship back, and if it wasn't for all these legal problems, I would have done it by now.'—Conrad Black

Aug. 10: Judge Amy St. Eve ups Black's bond by $1 million US to $21 million US, saying the former media baron had misrepresented how much he was worth. She denied a prosecution request to revoke Black's bail and have him jailed.

June 26: A U.S. judge decides not to revoke Black's $20-million US bond. U.S. prosecutors had accused Black of misleading authorities about the extent of his assets, and demanded he put up more collateral or be thrown in jail. The judge decided not to put the former newspaper tycoon in jail, but asked Black's lawyers for a revised financial statement before deciding whether to increase the bond.

June 19: U.S. prosecutors file documents with a Chicago court accusing Black of misleading authorities about the value of assets used to secure his bail. They demand the bail be revoked unless he puts up more of his holdings.

2005

Dec. 16: A U.S. Federal Court judge sets March 5, 2007, as the date for  Black's trial on charges of fraud, racketeering and obstruction of justice.

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Black's longtime friend and business partner David Radler is seen leaving the Dirksen Federal Courthouse in Chicago. ((John Gress/Reuters))

Dec. 15: 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 be sentenced to 95 years in prison.

Dec. 7: John Boultbee — the accountant who served as chief financial officer of 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 US and waiving his right to contest any future extradition from Canada. Boultbee is charged with eight counts of mail and wire fraud.

Dec. 1: Black appears in a Chicago courtroom and pleads not guilty to fraud charges in connection with the alleged looting of $80 million US 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 US 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.

Nov. 29: Black's arraignment on fraud charges is delayed again. This time it's put off a day (until Dec. 1) because of scheduling conflicts involving Black's two new Chicago lawyers, according to the U.S. Attorney's Office.

Nov. 22: 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.

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Black's chauffeur, John Hillier, wheels boxes out the back door of Hollinger offices in Toronto. ((Frank Gunn/Canadian Press))

Nov. 17: The U.S. Attorney's Office in Chicago charges 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 in 2000.

Nov. 3: Black sues the U.S. government, claiming the Federal Bureau of Investigation improperly seized almost $9 million US of his money.

Oct. 7: U.S. Attorney's Office in Chicago seizes $9 million US from sale of Black's New York apartment, saying proceeds were accumulated as part of an alleged fraud scheme.

Sept. 20: Former Black associate and long-time friend David Radler pleads guilty to mail fraud in connection with a plan to divert $32 million US from Hollinger International. Receives reduced sentence of 29 months in return for promise of co-operation.

May 20: Black, his chauffeur, John Hillier,and his personal assistant, Joan Maida, remove 12 boxes of files from Hollinger Inc.'s Toronto headquarters. The removal, which is caught on security video, 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.

April 20: Black – and his longtime business partner David Radler –resign as officers and directors of Ravelston Corp., the private holding company through which Black controlled his crumbling media empire. The announcement is made in Ontario Superior Court as Ravelston applies 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.

March 23: 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.

March 18: 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."

Feb. 24: 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."

Jan. 28: Hollinger Inc. agrees to put a $47.3-million US 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.

2004

Dec. 30: Black is named Canadian business newsmaker of the year by the Canadian Press and Broadcast News.

Nov. 22: 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.

Nov. 15: The U.S. Securities and Exchange Commission lays a civil fraud lawsuit against 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.

Nov. 2: Black resigns as chairman and chief executive of Hollinger Inc.

Oct. 8: A U.S. Federal Court judge throws out Hollinger International's $1.25-billion US racketeering lawsuit against Black and other former executives of the company.

Oct. 1: 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.

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Barbara Amiel, wife of Conrad Black, talks with reporters as she arrives at the federal court building in Chicago in 2007. ((Charles Rex Arbogast/ Associated Press))

Sept. 7: A group of five Canadian investors launches a class- action lawsuit against Black, his wife, Barbara Amiel, his chief lieutenant, David 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 took hundreds of millions of dollars they weren't entitled to.

Aug. 31: A special committee of Hollinger International issues a report saying former CEO Black and other executives took hundreds of millions of dollars they weren't entitled to. The report is made public by the U.S. Securities and Exchange Commission. Black's holding company, Ravelston Corp., dismisses the report, saying it was full of "misrepresentations and inaccuracies."

July 30,: The Delaware Supreme Court denies a Hollinger Inc. appeal of the ruling.

July 29: Hollinger International announces it had completed the sale of the Telegraph Group to Britain's Barclay brothers.

July 29: A Delaware Chancery Court judge rules that a shareholder vote on Hollinger International's sale of the Telegraph Group was not necessary and that it did not constitute "substantially all" of Hollinger International's assets.

July 1: Hollinger Inc. launches a lawsuit against Hollinger International over the $1.8-billion sale of the Telegraph Group Ltd. to the Barclay brothers. It wants to force a shareholder vote on the sale.

June 24: Hollinger International announces the sale of Chicago real estate worth $73 million US to Donald Trump amid reports that Black would try to block the deal. The building was the headquarters of Hollinger's Chicago Sun-Times paper.

June 23: Hollinger Inc. claims the sale of Hollinger International's main asset, Britain's Telegraph newspaper group, must be approved by its shareholders. If this were the case, it would give Black (as one of Hollinger International's controlling shareholders) the power to veto the sale.

June 22: Hollinger International announces the sale of its Telegraph Group in London for $1.65 billion.

June 8: Black loses his bid to have an injunction lifted that bans him from interfering with Hollinger International's sale plans for the Telegraph newspaper group. At the same time, Hollinger International's attempt to prolong the ban is also rejected.

May 7: Hollinger International amends its lawsuit against Black, alleging he and his associates engaged in racketeering. This allows Hollinger International to seek triple damages under U.S. anti-corruption laws.

March 23: Hollinger Inc. announces it would pay the $7.4 million US in interest it owes but would not accept a loan from Hollinger International.

March 12: Hollinger Inc. announces it will appeal the judgment that prevented Black from selling control of his newspaper group to Britain's Barclay brothers.

March 8: Black is removed as chairman of the London, England-based Telegraph Group by its directors.

March 5: Hollinger International offers Hollinger Inc. $7.4 million US to make an overdue interest payment on its debt.

March 2: The Barclay brothers' Press Holdings pulls its $605-million offer for Black's Hollinger Inc.

March 1: Hollinger Inc. fails to meet the deadline to make a $7.4-million US interest payment on one of its bonds. It has 30 days to make the payment.

Feb. 26: Delaware Judge Leo Strine, blocks Black from selling Hollinger Inc. to Britain's Barclay brothers Press Holdings International, saying it would hurt the interests of Hollinger International's minority shareholders. Hollinger International is "extremely pleased" by the ruling. Hollinger Inc. owns 72.6 per cent of Hollinger International. Pundits speculate that this is a huge loss for Black.

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British newspapers carried a story in January 2004 about the possible sale of the Telegraph Group to Britain's Barclay brothers. ((Reuters))

Feb. 18: Black appears in a Delaware court to defend himself against the lawsuit Hollinger International launched Jan. 17. The case is expected to centre on the issue of shareholder rights: whether a majority shareholder should be stopped from doing something that disadvantages minorities.

Feb. 13: Black files a lawsuit in Toronto seeking damages of $850 million for defamation from a number of Hollinger International directors.

Feb. 3: Black countersues to safeguard the transaction, alleging "blatant thievery" of his rights.

Jan. 26: Hollinger International launches a lawsuit seeking to stop Black from selling his 73 per cent voting stake in the company to Sir David and Sir Frederick Barclay.

Jan. 19: Black files court injunction in Ontario Superior Court to stop Hollinger International, and some of its directors from interfering with the sale.

Jan. 18: Black announces sale of his stake in Hollinger Inc. to Press Holding International for $600 million. The deal would give Press Holdings control of Hollinger International.

Jan. 17: The Hollinger International newspaper chain removes Black as its chairman and announces a $200 million US lawsuit against Black and associate David Radler over alleged financial irregularities.

2003

Dec. 28: The Canadian Press names Black business newsmaker of the year.

Dec. 22: Black is called before the U.S. Securities and Exchange Commission but refuses to answer questions, citing his Fifth Amendment right against self-incrimination.

Nov. 21: Hollinger International announces past earnings were overstated by $17 million US because of unauthorized non-compete payments to Black and others.

Nov. 18: A defiant Black attends a promotional event for his latest book, a biography of Franklin Delano Roosevelt. He faces a horde of reporters who grill him about the allegations against him. Black tells them he will repay $7.2 million US to Hollinger International but will remain the chairman of the parent company.

Nov. 17: Black announces he will step down as CEO of Hollinger International on Nov. 21 but then resigns on Nov. 19.

Nov. 12: Reports say American financier Nelson Peltz is negotiating to take control of the Hollinger newspaper group.

June 17: Hollinger International starts an investigation into $74 million US in "non-compete" fees paid to Black, other Hollinger executives and Black's Ravelston Corp.

May 22: Black agrees to loosen his grip on Hollinger International after shareholders complain about the poor performance of his newspaper empire.

April 2: Hollinger International Inc. reports loss of $238.8 million US for 2002, with no sign of upturn in 2003.

2001

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Conrad Black, right, stands in Britain's House of Lords. ((CBC))

Nov. 28: Hollinger sells its 15 per cent stake in Canwest for $271 million as the company continues to reduce debt.

Oct. 30: Black is given the title of Lord Black of Crossharbour as he takes his seat in the British House of Lords, the upper chamber of the British Parliament. He surrenders his Canadian citizenship to gain the peerage.

July 31: Hollinger sells most of its remaining Canadian newspapers to a company controlled by Michael Sifton, a Hollinger executive. Soon after, it sells the rest of the National Post to Canwest.

2000

Aug. 2: Hollinger sells its remaining U.S. community newspapers to four buyers for $215 million US, including 11 dailies, three non-dailies and 31 "shoppers."

July 31: In a deal with Canwest Global Communications, Hollinger sells its 13 major Canadian newspapers, 126 community newspapers, internet properties and half of the National Post for $3.2 billion.

April 25: Hollinger puts 350 North American newspapers up for sale to pay off its bank debt. By the end of the year, the sell-off will bring in $4 billion.

1999

Sept. 27: Conrad Black gets back the second newspaper he ever owned when Hollinger acquires the Sherbrooke Record in a swap with Quebecor Inc.

June 17: Black calls Prime Minister Jean Chrétien at the G8 summit in Cologne, Germany, in an unsuccessful bid to overcome Chretien's objections to Black receiving the peerage.

June 11: Black becomes a U.K. citizen one day after applying. This was done so Black could join the British House of Lords, scheduled for June 18. However the Canadian government objected and Black's peerage was put on hold.

1998

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Black holds up a section of the National Post in 1998, which he founded that year. ((Kevin Frayer/Canadian Press))

Oct. 27: The first issue of the National Post is published, spawning a newspaper war with the other Toronto dailies.

1993

Black publishes a memoir, A Life in Progress.

1992

July 21: Black marries journalist Barbara Amiel.

November: Hollinger buys a 23 per cent interest in the Southam chain from Torstar Corp.

1990

Black is named an officer of the Order of Canada.

1989

Mid-1989: Black's company buys controlling interest in the Jerusalem Post, the largest English-language daily newspaper in Israel, for $17 million.

1988

Feb. 1: Hollinger buys 15 per cent of the Financial Post for $6.9 million.

1987

Oct.-Nov. 1987: The company increases its interest in the London Daily Telegraph.

July: A subsidiary of Hollinger buys the magazine Saturday Night.

1986-1987: Hollinger acquires the remaining shares of Sterling Newspapers Ltd., a B.C. newspaper chain, 22 small-town newspapers in the U.S., three weekly papers in New York, and three French-language dailies and 20 weekly papers in Quebec.

1985

Black buys the U.K. newspaper the Daily Telegraph.

Sept. 17: Argcen Holdings, Hollinger Argus Ltd. and Labmin Resources Ltd. are amalgamated into Hollinger Inc.

1982

Norcen sells its stake after Hanna alleges the purchase was a precursor to a takeover bid, a breach of U.S. federal and Ohio state securities laws. Black signs an agreement to not violate provisions of the Securities and Exchange Act.

1981

Norcen Energy, a company owned by Black and his father, buys a stake in Hanna Mining.

1979

Tries and fails to acquire the Globe and Mail.

1978

July 14: Marries Shirley Gail Walters, with whom he has children: Jonathan (1977), Alana (1982) and James (1986).

July 13: Becomes president of Argus Corporation following a takeover a few weeks earlier.

1944-1977

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In his 20s, Black began buying small Canadian newspapers, and in 1971 he co-founded the Sterling Newspapers Group. ((Canadian Press))

1977: Sells the Sherbrooke Record.

1976: Publishes biography of Maurice Duplessis.

1974: Moves back to Toronto.

1973: Awarded a master's degree in history from McGill University.

1971: Buys La Nouvelle Revue.

1971: Co-founds Sterling Newspapers.

1970: Gets a law degree from Laval University.

1969: Black's family founds Ravelston Corp. as a vehicle for stakes in holding companies.

1969: Buys the Sherbrooke Daily Record, with David Radler and Peter White.

1966: Moves to Quebec. Buys the Eastern Townships Advertiser in Knowlton, Quebec from Peter White for $500.

1965: Graduates with a bachelor of arts in history from Carleton University.

1959: Expelled from Upper Canada College for stealing exams.

1945: Black family moves to Toronto.

Aug. 25, 1944: Conrad Moffat Black born in Montreal.