Obituary: The businessman will be remembered for being top of his game on the pitch and in the boardroom.
Said to be worth an estimated €2.8bn at one point, by 2010 he was €300m in debt with nine financial institutions chasing him for payments.
O’Reilly had it all. He was a famed sportsman, accomplished pianist and a brilliant mimic who loved company and had a charismatic personality.
Business was his life obsession and his astonishing successes included increasing the value of the US Heinz food giant from $908m when he took over in 1971 to $11bn in 1998.
At the peak of his career he owned an international newspaper empire, was the lead shareholder in Waterford Wedgewood crystal company and had investments in offshore oil-drilling, soft-drink bottling, fertilizer production and a vast private art collection.
He had bought a 28pc share in Independent News and Media (INM) in 1973.
The titles included the Irish Independent, Sunday Independent and the Evening Herald.
Over the next three decades he expanded his newspaper interests to include titles in South Africa, Australia, New Zealand and the UK.
Born on May 7, 1936, Tony O’Reilly was educated by the Jesuits at Belvedere College from the age of six.
It was these priests who disclosed to him at 15 the secret that his parents were not married.
They also told him how his father had abandoned a wife and four children in Wicklow before falling in love with his Dublin landlord’s daughter, 22-year-old Aileen O’Connor – O’Reilly’s mother.
At school O’Reilly was a good student but rugby was his passion.
In his final year at Belevedere he scored 42 tries in 21 matches, which was a school record.
When he went to University College Dublin to study law, he continued to play rugby and by the age of 19 he was picked by the Lions tour of South Africa.
He achieved further rugby honours on the Lions tours of 1955 and 1959 scoring 38 tries between the two tours – a record for the previous 100 years.
It was on the second Lions tour that the sportsman met his first wife, Susan Cameron, on a blind date in Sydney.
The couple married in 1962 and had six children in four years – Susan, Cameron, Justin and triplets Gavin, Tony and Caroline.
As O’Reilly’s career took off, the couple moved to the US to a Tudor style mansion overlooking a golf course in the affluent Pittsburgh suburb of Fox Chapel.
The house on 14 acres had a swimming pool and tennis courts.
The now millionaire businessman regularly commuted between the US and Ireland to look after his Irish business interests.
He expressed some regrets about his hectic business schedule.
“It’s the kids who pay for my peripatetic success and I’m really wondering if the price isn’t too high. Is anything worth being an absentee father?”
O’Reilly’s first job had been with UK management consulting firm and then with Suttons, an Irish company of general merchants.
Within five years he had been appointed chief executive of Bord Bainne, the Irish Dairy Board.
He was responsible for developing “Kerrygold”, Ireland’s first international dairy brand aimed at selling butter on the UK market.
Ahead of his time, O’Reilly used advertising techniques like radio jingles and TV slots to promote the product and sales soared.
Four years later he became head of the Irish Sugar Company and used the same techniques to boost the country’s sugar industry.
He was headhunted by the chief executive of the US Heinz corporation Burt Gookin to direct the company’s British subsidiary in 1969 and was quickly appointed senior vice president in charge of Heinz North American and Pacific operations.
By the age of 37 he had become company president and within less than two decades at the helm was the highest paid executive in the USA with a salary of €55m a year.
Around this time he met Chryss Goulandris, the daughter of a Greek shipping tycoon, in a New York hotel where he regularly stayed during business trips.
His first marriage had already broken down and he married Goulandris in 1994.
One of his gifts to his new wife was a €2.45m diamond ring which had originally been commissioned by Aristotle Onassis when he married former US first lady Jackie Kennedy.
The couple moved between their homes at Castlemartin in Co Kildare – a 26,000sq ft mansion on a 750-acred stud farm – a house in the Bahamas, another in Deauville in France and an Irish holiday home in Glandore in West Cork.
Through his business connections O’Reilly helped to raise over $100m through the Ireland Fund for worthwhile Irish charities and peace process projects.
He was knighted by Queen Elizabeth in 2001 for “long and distinguished service to Northern Ireland”.
Throughout his career he made firm friends with many world leaders. US President Ronald Reagan sent him a video message for his 50th birthday jokingly calling him a “mere child”, adding “in another couple of decades you will be old enough to think about running for public office”.
His friends included Zimbabwe President Robert Mugabe, United States Senator Ted Kennedy and US Secretary of State Henry Kissinger who dubbed him Ireland’s “renaissance man”.
Anti-apartheid revolutionary and South African President Nelson Mandela spent several holidays in O’Reilly’s home in the Bahamas and at Castlemartin.
In 1990 O’Reilly first invested in Waterford Wedgewood crystal. It was this company that helped to unravel his wealth.
When the company was teetering on the brink O’Reilly and his brother-in-law Peter Goulandris ploughed in excess of €400m to try and prop it up and lost millions when the company collapsed in 2009.
That year too, he lost control of his Independent News and Media titles in a takeover bid by Denis O’Brien. O’Reilly had so many borrowings he did not have the funds to fight back.
He now owed an estimated €300m to the banks and made efforts to pay some of this debt through the sale of his assets.
He sold Castlemartin for €26.5m, his townhouse in Fitzwilliam Square in Dublin for €3.2m and his house in Glandore for €1.5m.
He sold some minor paintings and sculpture from what is believed to be the most valuable private art collection ever assembled in Ireland but the location of much of the rest of the collection is unknown.
It included a painting by French Impressionist Claude Monet bought for $24.2m dollars and several major painting by Jack B Yeats.
Furniture from Castlemartin was also auctioned in September 2016.
O’Reilly was declared bankrupt in the Bahamas in November 2015. This did not affect his wife’s huge personal fortune as she was not a personal guarantor for her husband’s businesses.
He became a reclusive figure in recent years spending most of his time in the couple’s beachside villa, Lissadel, near Nassau, the capital of The Bahamas.
However, O’Reilly emerged from bankruptcy in recent months.
His creditors of Mr O’Reilly received a final dividend from his estate and the Supreme Court of the Bahamas closed the bankruptcy proceedings in December, on the basis that the whole of his property was realised for the benefit of his creditors.
His wife, Lady Chryss O’Reilly (73) died unexpectedly in August of last year.
The Irish Independent understands Mr O’Reilly’s children were all in Ireland in recent weeks.
He died in St Vincent’s Hospital on Saturday morning at the age of 88.
Of his business success he once said: “I’m often depicted as some super-confident guy. I’m not at all that certain. I envy others who are.
“I’m where I am now because of a lot of luck and a certain amount of hard work.”