At their height, the Blacks cut an imposing sight on the social scene.
For former media tycoon Lord Black of Crossharbour, it will be a rude awakening - at six in the morning - to his first day as an prisoner in a Florida jail.
Lord Black - or inmate 18330-424 as he is listed on the Federal Bureau of Prisons website - will climb out of the bunk bed in his prison dormitory, don his regulation green shirt and trousers and join the queue for the communal washing and toilet facilities.
Then, after a breakfast of "mediocre high-school cafeteria-type food", he is likely to begin a tightly regulated day of "work-calls", "controlled movements" and strictly defined "recreation time" before an early bedtime of 9pm.
It is a far cry from what the 65-year-old former chairman of Hollinger International is used to.
Before his six-and-a-half year sentence for fraud and obstruction of justice last year, multi-millionaire Black and his wife, journalist Barbara Amiel, had led what jurors heard described as a lifestyle of almost unbelievable excess.
Money stolen from Hollinger shareholders helped to finance a life so lavish that the Blacks owned two Park Avenue apartments in New York - one of these set aside solely for the use of their servants.
Their butler even had his own American Express card to finance their spending sprees.
Black's biographer Tom Bower predicted that the former multi-millionaire would be "traumatised" by his change in circumstances.
"He has been cosseted all his life," said Mr Bower. "He won't know how to handle it."
A revealing insight into Black's daily life for the next six and half years - or less depending on whether he earns points for good behaviour - is provided by the Coleman Federal Correctional Complex's (FCC) Inmate Information Handbook.
The front cover of the 39-page prison inmates manual.
Presented to every inmate on admission it provides a wealth of detail on inmates' daily lives, the dos and don'ts of prison life and - in Black's case, a telling contrast to the life he led on the outside.
As a "low-risk" inmate in Florida's largest prison, Black will live in the Low Security Unit, where bars are at a minimum and the prisoners' daily lives directed towards learning a trade for life after release.
With a fellow inmate for company in the dormitory-style cell, space and privacy are likely to be restricted.
These are not familiar surroundings for a man who at the height of his wealth owned mansions in Toronto and Palm Beach, apartments in New York, plus a luxury house in Kensington, west London.
And rather than the global movers and shakers who attended his lavish parties, experts say Black's new companions will be prison guards as well as other non-violent low-risk offenders including drug dealers and child pornographers.
Stripped and searched
Mr Bower, who helped expose Black's profligacy in his book Conrad and Lady Black, said: "Conrad Black is a very arrogant man. He will not like the idea of mixing with people who are poorer or less intelligent than he is. He will find that very hard to deal with."
On arrival Black will have been stripped, searched, given a medical examination and an identification card.
He would then have been issued with the standard prison clothing allowance, namely: four green shirts; four pairs of green trousers; four T-shirts; a pair of safety shoes; four sets of underwear and socks; bed-sheets; a belt; a pillow and a few toiletries.
Black left his Palm Beach home for prison surrounded by the media.
Black will be required to wear this clothing at all times before 4pm, apart from weekends, holidays and when he is en route to and from the recreation yard. He will be also be "required" to tuck his shirt tails into his trousers during the work day.
For a man whose wife was revealed to have five separate closets in the their London townhouse for evening gowns, shoes and handbags, the contrast will be a marked one.
And for someone used to having his own way, Black will discover that there are regulations governing his every move.
Among the prohibited acts are fighting, blackmail, extortion and stealing from other inmates. Breaking these rules can result in loss of parole, or time spent in "disciplinary segregation" - solitary confinement.
Other, less serious infractions, include unauthorised use of the telephone, using abusive or obscene language and "unauthorised kissing or embracing".
Mr Bower said: "I predict he will have major problems adjusting to the idea that other people can tell him what to do.
Black was driven the 220 miles to Coleman FCC
"The important thing about Conrad Black is that he has never felt that he needed to obey the rules. One of the reasons he stole so much money was that he genuinely felt the rules did not apply to him."
Compared to his former jet-set lifestyle, the daily life of inmate 18330-424 is likely to be somewhat mundane. With a taste for the finer things in life - his lifestyle was described to jurors as "champagne and caviar" - Black may need to adjust his culinary standards.
A former inmate told the Toronto Star that food at a US minimum-security prison was high in starch, with "lots of spaghetti and fried and baked chicken, macaroni and cheese".
Black will be expected to hold down a job during his incarceration. But instead of the £7m that an internal company inquiry estimated he stole from shareholders, his rewards will be somewhat more modest.
Rates of pay in Coleman range from 23 cents (12p) an hour for unskilled jobs such as working in the laundry, to "First Grade" pay rates of $1.15 (55p) an hour for skilled workers such as carpenters or plumbers.
But while the pay may be a fraction of what he was used to earning, it is how much he is permitted to spend in prison that is likely to surprise him.
At his trial, the court heard how on a single day the Blacks spent $2.6m (£1.3m) on a diamond ring and $604,000 (£302,000) on an antique brooch. Over six years Black billed his company $1.4m (£700,000) for staff wages alone.
Now he is in prison, he will be allowed to buy goods from the commissary to the value of $290 (£145) a month. Even that modest amount is regarded as a "privilege", which can be withdrawn if rules are broken.
During his leisure periods Black is likely to have access to a television in a communal area.
THE BLACK FACTFILE
Born in Montreal in 1944 to a wealthy brewing family
At his height Black owned the Daily Telegraph and 400 smaller papers in North America
In 2004 his personal wealth was estimated at £175m
Married journalist Barbara Amiel in 1992
Became a life peer in 2001 after renouncing Canadian citizenship
Sentenced to 6.5 years in a US prison for mail fraud and obstruction of justice
And from 4pm to 8.30pm every day he will be also be offered the choice of activities designed to "maintain a healthful living and the enjoyment of participating with others in structured activities". These include soccer, softball, cricket and "boccie ball".
Compared with higher-security jails, the visiting rules for inmates in Coleman are relatively relaxed.
But when Black's wife Barbara does visit him she will discover that while she is allowed to shake his hand, kiss and embrace him at the start and end of each visit, such behaviour is prohibited at all other times.
She herself will be subject to strict sartorial rules: no "provocative" clothes or styles "not in good taste" are permitted. Skirts must be no higher than two inches above the knee and "plunging necklines" are banned.
One comfort for the couple will be that Coleman is just 220 miles - about three and half hours drive - from the Blacks' beachfront home in Palm Springs home, scene of a reported "farewell party" for the disgraced peer over the weekend.
It means Lady Black is unlikely to avail herself of one of the local motels that the manual recommends for prison visitors - the Super 8 Motel at nearby Wildwood where room prices start at just $100 (£50) a night.