By Alison Swersky
Business reporter, BBC News
Conrad Black is clinging to what could be the last shred of freedom following a guilty verdict by a US court.
Black's wife Barbara Amiel is well known for her lavish tastes
Convicted on three charges of fraud and one of obstructing justice, Black staved off the cells a little longer with a $21m (£10.5m) bond.
On Thursday, he will find out whether he can leave the United States between now and his sentencing hearing on 30 November.
The charges carry a jail term of up to 35 years, and he could also lose a substantial part of his assets.
As he faces the prospect of spending a good portion of his life rubbing shoulders with thieves and murderers instead of celebrities and senior statesmen, Black persists with a steely show of defiance.
His lawyer Edward Greenspan says the fallen media tycoon will appeal the sentence to dispose of what Black calls these "false charges".
Despite the Canadian-born 62-year-old's eternal confidence - or supreme arrogance, his critics may say - many legal experts predict that his appeal will fail and that he will soon have to get used to a more basic and restricted way of life in a US prison.
As a Canadian citizen, Black could have had the opportunity of serving his time in one of the country's minimum-security prisons, often called "Club Fed" for their relatively relaxed regime. This is how his former business aide and partner-in-crime David Radler will serve his 29-month jail term.
But Black renounced his Canadian citizenship in 2001 to become a British peer - a title he retains - and as a result of his criminal convictions he is unlikely to be allowed back into Canada even on a visit, immigration officials have said.
A taste of the humiliating road ahead as a convicted felon came when Black, once the owner of the world's largest newspaper empire, was forced to hand over his UK passport to the judge in Chicago, Amy St Eve, amid fears he would flee the country.
But if that were not sufficient punishment, Black also faces losing all his money and everything he has ever owned.
A combination of expensive legal fees for top-class representation at his criminal case, further civil litigation following the problems at his former company Hollinger International and a potential raid on his assets amid prosecutors' claims that he has been hiding the scale of his wealth, could reduce Black to personal poverty.
Prosecutors have said that even though Black was cleared of abusing company resources to fund his extravagant lifestyle - the most serious of the 13 charges he faced - his fraud convictions were enough to support a probe into his finances.
If the prosecutors are successful, Black could be forced to hand over his $35m Florida mansion and the $9m proceeds from the sale of his Park Avenue apartment in New York among other coveted assets.
This all could come as too much of a shock to the system for his wife, the newspaper columnist Barbara Amiel. She once said in an interview that "her extravagance knew no bounds".
Many commentators wonder whether Lady Black, whose marriage to Black in 1992 was her fourth, will have the sticking power to overcome her husband's loss of status, influence and riches.
Whatever the road ahead for Black - and it is likely to be long and full of pot holes - it is difficult to imagine the once corporate titan laying down his sword to spend the rest of his life outside the realms of the media, either behind or making the front pages.