The unexpected downfall of Tony O’Reilly was all over the papers. It was January 1963 and for the first and only time in his life, O’Reilly had been dropped from the Irish rugby team.

Despite having scored a try in the previous game against France, it was not enough. Ireland had lost the game badly and O’Reilly was out of the team against England. Time for new blood.

"Seldom can the slings and arrows of outrageous fortune have afflicted anyone in rugby as severely as O'Reilly," The Irish Times reported.

O’Reilly’s try had made him a “hero”, but now he had been “cast into the outer darkness”.

"For O'Reilly it came as a jolt to a self-confidence which had received remarkably few," Ivan Fallon concluded in O'Reilly's 1994 biography The Player.

O’Reilly made it back to the Irish team, and went on to play for another seven years. Now, over 50 years later, O’Reilly has found himself back in the papers for the wrong reasons after a stellar business career.

This time it was more than a game: it was money, but also pride.

Last May, AIB moved against O'Reilly seeking a summary judgement for €45 million against his investment companies in the High Court.

Three times O’Reilly, once Ireland’s richest man, was called “insolvent” by the bank’s legal counsel.

The following day the Irish Independent, a newspaper he had once controlled, pronounced him "broke."

O’Reilly had fought hard to prevent such an action behind the scenes, but AIB was determined to break ranks with his other banks to secure its position. The move forced him to publicly put his beloved Castlemartin estate in Co Kildare on the market for €30 million.

A distressed sale would have been unimaginable for O’Reilly less than a decade ago.

O'Reilly lost his fortune on two investments: Waterford Wedgewood and Independent News & Media. One fell rapidly after the other.

For five years from 2004 on, O’Reilly and his brother-in-law Peter Goulandris invested €400 million into the glass maker. They hoped to reinvent the business for the modern age and try to retain as many jobs as they could in the southeast.

It was not enough to turn around the luxury goods maker. In January, 2009 Waterford’s banks took the business over wiping out O’Reilly’s entire investment.

O'Reilly was left with substantial debts following the collapse of this business, including €40 million owed to Anglo Irish Bank.

The following month, O'Reilly announced he planned to step down as chief executive of INM on May 7th, his 73rd birthday.

INM had historically been a cash cow for O’Reilly, earning him €14 million annually in dividends on average during the boom, on top of a generous salary. But the dividends dried up as INM creaked with financial strain.

INM was in serious trouble. After a cash-sapping war with rival shareholder Denis O’Brien, its share price had collapsed under the weight of its debts built up during the boom as well as sharply declining revenues because of the economic recession and move of its print readers online.

O’Reilly’s shares in INM had been worth up to €1 billion during the boom, but now they worth a tiny fraction of that.

O’Reilly was in serious trouble. He had borrowed against the value of his INM shares. His lifestyle was expensive. It was time for action.

Behind closed doors, O'Reilly and his financial advisor Bernard Somers met his many bankers to outline the perilous situation. At his peak, he and his companies owed five banks over €250 million, which he set about trying to pay back.

O’Reilly agreed with his banks that they would not move against him. Instead he would steadily sell off his assets and do his best to repay them what he could.

He sold his remaining shares in Heinz, the food giant he had once led. Some artworks were quietly trickled onto the market. His gains from the sale of Landis + Gyr, a Swiss smart-metering firm, was handed over too. But it was not enough.

Hopes of selling Providence Resources, an exploration firm where he was a large shareholder, to the Chinese failed to happen. A company restructuring in INM reduced the value of his shares still further.

O’Reilly began to sell his homes. His private residence on Fitzwilliam Square was sold. He tried to find a buyer for his holiday home in Cork. But for AIB things were not moving fast enough, so it decided to seek a summary judgement in order to protect its interests.

After AIB moved on him, O’Reilly put Castlemartin, scene of so many lavish banquets with world and domestic leaders, on the market.

O’Reilly is believed to have been close to selling the estate just prior to AIB making its move, but this failed to happen. He has a home in the Bahamas too which may also now have to be sold.

It has been a very public tail-end to a glittering career.

Dr Michael Smurfit, the paper and packaging tycoon, has spoken out in his defence. "It's really, really sad to see one of the creators of modern Ireland in this sort of difficulty, and it's a sad reflection on the way society is that we take delight in seeing the 'big' brought down. There but for the grace of God go I. That's the way I look upon it," he said.

Financier Dermot Desmond called for AIB to show "sensitivity" to O'Reilly. "Money is replaceable, honour is not, and he has left great honour with what he has done," he said.

Even Denis O’Brien, the billionaire telecoms tycoon, has paid tribute to his former foe in the battle for INM. “I would have the utmost of sympathy for him and that is genuine,” O’Brien said last month. “People say how could you have sympathy for him after the boardroom battle? I totally do because I can relate to difficulties. Everyone has this false impression that everything in business is a staircase you know, always going up. It is never like that.”

A documentary crew from RTE is in thick of production to make a documentary on the O’Reilly story before Christmas.

A new biography by the broadcaster Matt Cooper, to be published by Gill & Macmillan, is also being worked on.

O’Reilly’s finances may have gone into the darkness, but his remarkable life remains a subject of fascination.