The bidding for a 40-carat diamond engagement ring, which shipping magnate Aristotle Onassis gave the former First Lady in 1968, continued to go up and up at the auction of Jacqueline Kennedy’s estate in New York in 1996. Finally the bidding for the Lesotho III ring closed at $2.5 million to gasps of astonishment from a packed auction room as Al Lippert, a board member of Heinz, placed the highest bid on the behalf of an unknown party. Shortly after, Conor O’Clery broke the news in The Irish Times that the successful bidder was Tony O’Reilly, then chairman of American food giant Heinz and the head of Irish publisher Independent Newspapers.

“The attraction of the Onassis ring to Dr O’Reilly was its symbolic significance, according to a source close to the Heinz chairman,” O’Clery reported. “Having been given first by a Greek shipping owner to the wife of an Irish American President, it now goes to Chryss O’Reilly, who also comes from a Greek ship owning family and is married to an Irishman.”

Acquiring the ring was a symbol of love, and also of great fortune. Chyrss and Tony O’Reilly were estimated at that time to have a combined fortune of more than a billion euro. 

The racing world mourns

Chryss O’Reilly was a remarkable woman who died suddenly at the age of 73 this week. She was born into the wealthy Goulandris Greek shipping family but carved out her own career in horse breeding and racing internationally. She owned, bred, trained, and raced horses primarily under her Petra Bloodstock Agency and Skymarc Farm businesses, where she has been estimated to have more than 100 horses in training and the same number of broodmares. Only last weekend, two horses she bred came in as winners at Newbury and at the Curragh. The Racing Post reported on August 22 that O’Reilly, who was also the owner of Haras de la Louviere in Normandy, sold a colt for a sale-topping €200,000, which was described by its new owner as “one of my favourite colts in the sale.” Thoroughbred Daily News described her passing with the headline: “Racing World mourns death of Lady O’Reilly.”

In 2013, she was inducted into the Irish National Thoroughbred Association Hall of Fame at its annual awards at the Heritage resort in Co Laois. “Among the stars she has bred are Equiano, Helissio, Highest Honor, Lawman and Silver Frost, while her black and white striped silks with blue cap have been carried with distinction by homebreds such as Chinese White,” The Racing Post noted. Among the Irish trainers she worked with were Dermot Weld, Eddie Lynam, and Kevin Prendergast; she also worked with leading trainers in France and Britain.

A Greek family fortune

Chryssanthie Goulandris was born in New York in 1950. Her family hailed from the Greek island of Andros and the family’s interest in shipping went back generations. The Gouldandris family moved to London in 1941 after Germany invaded Greece, before later that decade her father, John, moved to New York where he lived in the Savoy Plaza Hotel. He married Maria Lemos, another scion of a Greek shipping family whom he had known since childhood.

“The family took full advantage of the shipping boom that followed the war at one stage either owning or managing more than two hundred ships, many of them Liberty vessels, and they were among the first to move into the highly profitable oil tanker boom of the early 1950s,” Ivan Fallon noted in The Player, his 1994 biography of Tony O’Reilly.

Chryss Gouldandris’s father died at 42 when she was just three years old and her younger brother Peter was just a baby. After private schooling, she studied French civilisation in the Sorbonne, before joining the family business, which besides shipping had extended into property and trading in commodities. According to Fallon, she turned $5,000 into $1.5 million trading on commodities futures before she took a disastrous bet on the price of silver. “Chryss’s $1.5 million was turned into a large minus $400,000 in three weeks. She retired from the commodities market wiser, but poorer,” Fallon noted.

She found her feet, however, in her passion for racing and breeding. Two of her uncles: George Goulandris and Constantin Goulandris, owned and raced winning horses. Chryss Goulandris was soon breeding her own winners, and she became close to two great French trainers, Etienne Pollet and Francois Boutin. She was now in her early 40s, an heir to a great fortune but also a successful person in her own right. It was then she met an Irish man.

Falling in love with Tony O’Reilly

Tony O’Reilly was in New York trying to find potential investors to invest in and grow Waterford Wedgwood, an iconic glass and homewares maker. O’Reilly was considered Ireland’s richest man at the time and was in his mid-50s, and a charismatic business leader with the strong build of a former international rugby player. He was divorced a number of years from his first wife, the Australian Susan Cameron with whom he had six children: Susan, Cameron, Justine, Gavin, Caroline, and Tony Jr. “Chryss Gouldandris was a striking, attractive, sophisticated, and multilingual woman, a dozen years his junior, who instantly intrigued him,” Fallon wrote in The Player.

Tony O’Reilly met Chryss Goulandris for the first time along with her brother Peter in the five-star Pierre Hotel in New York. They were interested in O’Reilly’s business pitch, but there was no spark yet on Chryss Goulandris’ side. A year later, the siblings bumped into Tony O’Reilly again at a race meeting in the Phoenix Park sponsored by Heinz.

Chryss Gouldandris now hit it off with O’Reilly, and a romance began. Later Tony O’Reilly took his children to visit the Goulandris family in Lyford Cay in the Bahamas, and then the couple met again in O’Reilly’s home and stud farm called Castlemartin in Co Kildare.

In September 1991, Tony O’Reilly married Chryss Gouldandris in Lyford Cay. Chryss O’Reilly now found herself in the public eye in Ireland where her husband was a famous business leader and former sportsman. She continued with her passion for horses but also took on her husband’s interests.

She became a director of the Ireland Funds, a philanthropic organisation that O’Reilly helped set up that has raised $600 million for good causes. Her family invested in Waterford Wedgwood and she was active on its board trying to save the company. When this company failed, she and her brother lost hundreds of millions, but they bore the losses. She also became chair of Barretstown Castle, a children’s charity championed by her friend the actor Paul Newman.

She was a quick-witted and gracious host at the glittering banquets in Castlemartin and elsewhere hosting everyone from Nelson Mandela to Sean Connery that were part of how her husband did business. She was also chair of the Irish National Stud for more than a decade. There were a few controversies during this period, but there was success too and she also entertained both Queen Elizabeth of England and on another occasion her daughter Princess Anne. 

Standing by her man

When the Irish financial crash came, Tony O’Reilly saw his fortune, once estimated at more than €1 billion, decimated. With his brother-in-law Peter Goulandris, he had invested too much in Waterford Wedgwood, which despite its best efforts was losing out to cheaper manufacturers in China and Eastern Europe. This left him with fewer resources available to take on a costly takeover of his newspaper business, Independent News & Media, by the tycoon Denis O’Brien, which was followed immediately by a crash in advertising revenues due to the broader economic crash. At the same time, hopes of an oil find off the coast of county Cork via his stake in Providence Resources were also dashed. This left O’Reilly with substantial debts and assets that had been wiped out in value.

O’Reilly owed the former Anglo Irish Bank (later renamed IBRC), which had been nationalised, €60 million. He paid off part of this with money he made from selling shares in Landis+Gyr, a smart metering firm once led by his son Cameron O’Reilly.

This left a debt of about €35 million owed by O’Reilly-related entities, and he also had substantial debts with another almost state-owned bank called AIB as well as other banks. O’Reilly’s banks all tried to put Chyrss O’Reilly, whose assets were entirely her own, under pressure to pay off her husband’s debts. A deal was nearly done with IBRC as Chryss O’Reilly agreed to pay off much of her husband’s borrowings. But in the politically fraught times, a deal kept being delayed. Then the state liquidated IBRC overnight, and his loans were sold off instead as part of a bundle to Lonestar, a Dallas-based fund led by John Grayken.

Tony O’Reilly tried to behave honourably by selling off assets including Castlemartin, where his parents were buried, and which Chyrss O’Reilly helped transform as a stud. But it was not enough for his banks, and AIB pushed hard against him in 2014, seeking a summary personal judgment of €22 million in the courts.

In 2016, O’Reilly went bankrupt in the Bahamas. The numbers involved to repay his debts were simply too great, and his banks, perhaps due to his high profile or other reasons, were not prepared to cut the same deals they did for other businessmen.

Chryss O’Reilly stood by her husband all the way. Matt Cooper, in his biography of Tony O’Reilly, called The Maximalist, describes how she cared for her husband when he hurt his eye in 2009 and had to rest motionless for a month in a darkened room to save his sight. Her love did not waver for a man who, with Tony Ryan and Michael Smurfit, put Irish business on the world map. 

A lot of joy

On Thursday night, the President of France Galop, a former equestrian showjumper, and scion of a famous European banking family Édouard de Rothschild, told Paris Turf he had been moved by the passing of his friend Chryss O’Reilly. “She died on Wednesday afternoon while I had lunch with her at Haras de Meautry the day before. No one could have expected this very sad news. We had been partners since the end of the ’80s, for me she represented elegance and discretion. We have had a lot of joy at the races together, including recently.”

Chryss O’Reilly was only 73. She spent her final days near horses. She was adored by Tony O’Reilly and loved by her and his family.