Talking of big business deals and his plans for Blackpool, the football club he owned, he showed no concern that he was heading for prison, guilty of raping a 16-year-old girl.
Dressed in the vivid orange colours of Blackpool, he was surrounded by his family and close friends, including Billy Bingham, the former Northern Ireland football manager, and Louise Ellman, leader of Lancashire County Council.
There was virtually no mention of the three weeks at Liverpool Crown Court which had been hearing accounts of his philandering on a prodigious scale.
Instead, as ever with Oyston, the talk was of football transfers, property developments, plans for a new stadium outside Blackpool, his stake in Sunday Business, a new national newspaper, and the addition of Radio Belfast to his network of local radio stations.
There were plenty of jokes about his legal fees but with a fortune estimated at pounds 40m, they should not hurt him too much.
His wife, Vicky, his daughters and son had been forced listen to how he had a stream of affairs and the lurid details of a three-in-a-bed session in the four-poster at their family home.
Witnesses told how he often wined and dined young women in London, while his wife stayed at home. Many families would have chucked him out long ago.
A natural actor - ironically he once played in the 1970s television series, Crown Court - he is a one-off in the staid, boring world of business, with unfashionable trademark long hair and goatie beard, coupled with his fondness for wide-brimmed hats and fur-trimmed coats.
His style is tacky, something belonging to a different age. His home is a Gothic mansion high on the hills near Lancaster. Inside, there is a great medieval hall, the centrepiece of which is a modern table-tennis table.
In the garage there is a gold Rolls-Royce, bomb-proof with curtains around the windows, and a cocktail cabinet and television set in the back. He last used it to go to the Blackpool Illuminations. Parked next to it is a rare Lamborghini. They are hardly ever used, he prefers to cadge lifts everywhere from his employees. Until recently, bison grazed on his front lawn.
When in London, he entertains at Windows on the World, the restaurant at the top of the Hilton - itself a throwback to the Seventies.
He made his money by striking tough deals and shameless self-promotion. For years, night after night, he would appear on television commercials in the North, extolling the virtues of his estate agency chain before falling backwards fully clothed into a swimming pool.
One deal made his fortune. At the height of the property boom he sold the estate agency to Royal Insurance for pounds 33m.
His timing was superb, but his negotiations were characterised by a ruthless streak.
Royal wanted to get into estate agency - he had the biggest chain in England with 98 branches. According to those close to the negotiations, he drove the price up and up, until now, in the cold light of the property recession, it looks like a ridiculous figure.
That cajoling, bullying streak is another side to his nature which is rarely seen in public but is constantly present in business meetings.
He has an attention span of zero, hardly listens to what he is being told for any length of time, is constantly thinking of the next money- making opportunity, and how he can exploit it to his advantage.
The City's antipathy was explained by his sleight of hand on TransWorld, which owned radio stations and the Miss World contest, where he consistently denied he held more than 29 per cent of the company, yet it was obvious to everyone that behind some of the nominee names on the share register lurked his friends. It was typical Oyston ploy - cunningly designed to conceal his involvement.
Almost a mini-Robert Maxwell in the way he surrounded himself with expensive advisers and always kept people waiting, he went from meeting to meeting, riding roughshod over people's lives, expecting them to comply with his timetable.
Employees were used to being telephoned at all hours and subjected to roastings. A favourite ploy was the personal touch, a hand on the arm or a pat on the back, as if that was compensation for the hell they had just been put through.
He always had to get his own way and lacks a conciliatory side to his personality. When Lancashire Enterprises, a company he jointly owned with Lancashire County Council floated on the stock market, its advisers said they could not sell shares to the public with him on board. Instead of abiding by their decision he reacted furiously, threatening legal action.
At one time a close friend of Neil Kinnock, the former Labour leader, Oyston was once one of the party's biggest individual backers.
These days, he does not enjoy the entree with the Labour leadership that he once did. In truth, he is apolitical - the other night he was saying how he hated the soubriquet "socialist millionaire" - and counts Tory MPs, notably Sir Tom Arnold, and Harold Elletson, among his closest friends.
He was never accepted in London. The City tends to regard him with a mixture of disdain and open hostility.
The feeling is mutual. He likes to come down from the North, hold court in the Hilton, have a few meetings, then go back again. With his hippy looks and previous open support for the Labour Party, he will never find acceptance in the Square Mile.
Increasingly in recent years, evidence has emerged that this rather odd character, is the target of a concerted smear campaign by senior local Conservatives.
For once, where such plots are alleged, the proof exists. Three Conservatives, Robert Atkins and Lord Blaker, both former ministers, and Bill Harrison, a prominent Blackpool builder, encouraged a local self-styled anti-corruption campaigner, Michael Murrin, to look into Oyston.
Unknown to them, Mr Murrin taped their phone calls and kept the letters about his campaign. Years later, Oyston was able to buy them from him.
The campaign against him has been raised in Commons Early Day Motions. The trio say they did it because they wanted to investigate his dealings with local councillors.
In his rape trial, the conspiracy was raised again. It was pointed out that he was arrested just three weeks before a court case against the former ministers was due to be heard in London. In the event, the case was thrown out. The former ministers had no involvement in Oyston's arrest and prosecution.
Used to being constantly on the move, pacing up and down, always on the phone, he will go mad in prison.
For one thing, he will be denied the commodity he loves best after money - women.
His womanising was extraordinarily prodigious and blatant. Women, normally strikingly beautiful, were always around him, especially on his trips to London.
He once boasted of having had sex with two Miss Worlds. As of now, those days are but a distant memory.Reuse content