Described as everything from "very arrogant" to a "bombastic megalomaniac", Conrad Black is not a man who ever tolerated - or even considered - losing at anything.
Lord Black has built a prodigious newspaper empire
In political debate or business, he liked to eat his many rivals for breakfast; before jetting off in the company's private jet for dinner in an exclusive restaurant.
Yet following the decision of a judge in the tiny US state of Delaware, the 59-year-old peer is suddenly having to endure a crash course in humility.
Judge Leo Strine did not mince his words in his personal criticism of Lord Black, accusing him of acting "in a cunning and calculated way" by attempting to sell-off his newspaper titles to the Barclay brothers, against the wishes of his former company Hollinger International.
Judge Strine said Black "repeatedly behaved in a manner inconsistent with the duty of loyalty he owed the company".
The judge has put control of the papers, which include the Daily Telegraph, Jerusalem Post and Chicago Sun-Times, back in the hands of Hollinger International, Black's new sworn enemy.
Hollinger International would no doubt claim Lord Black is the author of his own downfall, thanks to an age old vice - greed.
His dismissal as chairman came as a result of an internal investigation at Hollinger International which concluded that the peer and his friends, without authorisation, siphoned off millions of pounds of company funds to pay for their extravagant lifestyles.
'Hypocrites and ingrates'
Lord Black has denied this, but the matter is now waiting to go to court, with Hollinger International suing for $200m.
The lawsuit further alleges that Lord Black showed a breathtaking disregard for Hollinger International's minority shareholders, and accuses him of being an abusive bully who had "absolute power" over the company's board.
To back up its case Hollinger International released a leaked Lord Black email, which sent to fellow executives.
It said: "We now have an unsatisfactory situation where a number of the shareholders think we are deliberately suppressing the stock price, some others think we are running a gravy train and a gerrymandered share structure, and we think they are bunch of self-righteous hypocrites and ingrates."
Born the son of a wealthy Toronto businessman and investor in 1944, Lord Black started buying provincial Canadian newspapers in the 1960s.
Black's empire really took off when he inherited his father's fortune in the 1980s and moved to the UK.
In 1992, the confirmed Anglophile took control of the Daily Telegraph, pitting himself against Rupert Murdoch, proprietor of the Times, in a two-horse race to be the voice of Britain's Conservative establishment.
But the comparison with Mr Murdoch, while frequently made, was misleading.
Although Lord Black was the third biggest newspaper magnate in the world, his holdings are not in quite the same league as Mr Murdoch's News Corp, which spans satellite broadcasting, film, book publishing and newspapers.
Lord Black confined his interests to ink and paper, cultivating the image of a newspaper magnate of the old school: William Randolph Hearst to his friends, Citizen Kane to his enemies.
He has had numerous run-ins with governments, journalists and shareholders, including opponents within his company, over the years but always managed to come out on top - until now.
His downfall is likely to cause much gloating in his native Canada, where his appetite for newspaper acquisition, outspoken conservative views and abrasive tongue have made him a bete noire for liberals.
Former Canadian Prime Minister Jean Chretien is a particularly avowed foe ever since the Liberal party premier blocked his British peerage in 2000, and Lord Black was forced to renounce his Canadian citizenship.
The peer's future now rests with the civil case being brought against him by Hollinger International.
Lord Black may be a multi-millionaire, but if the case is anything like as bad for him as the one in Delaware, he could be left with a hefty settlement to pay.
It would be an ignominious end to a decades-long winning streak.