Anthony J.F. O’Reilly, a charming, high-flying, Irish-born former chairman of the H.J. Heinz Company, who also owned newspapers, luxury brands and trophy homes in France and the Bahamas, only to lose nearly everything in his eighth decade, died on May 18 in Dublin. He was 88.

The Irish Times and other Irish newspapers, citing a family spokesman, reported that he died in a hospital. No cause was given.

From his earliest days, Mr. O’Reilly, who was known as Tony, displayed an embarrassment of gifts. He was an elite-level rugby player while still in his teens — the “redheaded pinup boy of Irish rugby,” as The Guardian put it. His talent for business was equally precocious.

At 26, as the marketing head of the Irish Dairy Board, he created the brand Kerrygold to sell Irish butter to English grocery shoppers, and it is still one of the country’s best known global exports.

Mr. O’Reilly was recruited by Heinz to run its businesses in Britain in 1969, then moved to the company’s Pittsburgh headquarters, where he rose to chief executive and became the first chairman from outside the Heinz family. Under his leadership, Heinz’s value increased twelvefold. Business Week called him “one of the world’s most charismatic businessmen.”

“He has a million stories and tells all of them well,” a Heinz director, Richard M. Cyert, told Business Week in 1997. “When you sit down to lunch with him, it’s like going to a movie theater for entertainment.”

Mr. O’Reilly played tennis at the White House with President George H.W. Bush, who reportedly considered him for commerce secretary. He helped create the Ireland Funds, whose promotion of peace projects in Northern Ireland undermined fund-raising by the Irish Republican Army among Irish Americans. Queen Elizabeth II knighted Mr. O’Reilly for his service to Northern Ireland in 2001.

He had a highly unusual arrangement at Heinz that allowed him also to build his own business empire. He would fly to Dublin in the company Gulfstream jet after work on Friday, fitting in meetings and sometimes a rugby match. Then he’d jet back to Pittsburgh to be in his office by 8 a.m. Monday

Perhaps more successfully than any other entrepreneur, he rode the Irish economic boom of the 1990s and 2000s known as the Celtic Tiger, becoming the country’s richest man and reportedly its first billionaire.

He established his newspaper group, Independent News & Media, with the purchase of The Irish Independent, the country’s leading newspaper, in 1973. It grew to include more than 100 properties, including The Independent of London and papers in Australia, New Zealand and South Africa, bringing Mr. O’Reilly access and influence with political leaders.

In 1990, he bought Waterford Wedgwood, the Anglo-Irish crystal and china company, with the ambition to build it into a global luxury group along the lines of Gucci and LVMH.

Mr. O’Reilly acquired the lifestyle and famous friends to match his prestige businesses. His Irish base was Castlemartin, a 750-acre estate, where President Bill Clinton and Nelson Mandela were guests.

He also had a Georgian mansion in Dublin, a beachfront home on Lyford Cay in the Bahamas and a chateau in Deauville, France. His art collection included a $24.2 million Monet and works by Picasso and Matisse.

Although Mr. O’Reilly built his fortune with his ample compensation from Heinz, the company’s humdrum brands did not reflect his aspirational tastes. He once said of Heinz’s ubiquitous ketchup, according to The Irish Times, “We have been producing it, like chunk, chunk, chunk, every day in 100 factories around the world.” Owning newspapers, on the other hand, offered “more than you can get out of baked beans,” he said.

It didn’t stop him from lavishly spending Heinz’s money in an effort to impart glamour to the company. He flew hundreds of guests to Ireland for an annual gala ball and a thoroughbred race, the Heinz 57 Stakes.

In 1996, Forbes named him the fourth highest-paid chief executive in the United States, even as the company’s business results had disappointed for several years. “Tony O’Reilly’s ego and paycheck are bigger than his accomplishments,” the magazine wrote.

He stepped down as Heinz’s chief executive the next year, though he remained its chairman until 2000. In his early 60s, he turned his full-time attention to his own businesses, which, in addition to newspapers and luxury wares, included oil exploration and a company that converted castles into hotels.

Like many business empires, Mr. O’Reilly’s was built on debt. When the global financial crisis blew in like a Category 5 hurricane in 2008, Mr. O’Reilly’s ventures buckled. He lost control of his media properties to a longtime rival Irish tycoon, Denis O’Brien.

In 2009, Waterford Wedgewood, into which Mr. O’Reilly had poured large personal sums, failed and went into receivership.

Pursued by creditors, he sold many of his artworks and his beloved Castlemartin, which the American telecom billionaire John Malone bought for 7.4 million euros, or about $10.2 million, in 2015.

Lawyers for Mr. O’Reilly said he owed eight banks €195 million, or about $268.9 million, at the time. In 2015, when he was 79, he declared bankruptcy in the Bahamas.

Anthony John Francis O’Reilly was born on May 7, 1936, in Dublin, the only child of John and Aileen O’Conner. His father was a civil servant.

According to a 2015 biography of Mr. O’Reilly, “The Maximalist,” by Matt Cooper, Tony, as he was known, learned when he was 15 that his parents were not married. His father had left a wife, with whom he had four children, for Tony’s mother. The couple formally wed in the mid-1970s.

Tony O’Reilly’s elite rugby career began in 1955 at age 19, when he toured internationally with the Lions, a team composed of the best players in Britain and Ireland. He was the youngest player on the Lions and still holds its record for the most tries — the equivalent of a football touchdown — scored in test matches (games against other national or regional teams).

On a rugby tour of Australia, Mr. O’Reilly met Susan Cameron, whom he married in 1962. They had six children, including triplets, before divorcing in 1990. His second wife, Chryss Goulandris, a Greek shipping heiress whom he married in 1991, died last year.

Mr. O’Reilly is survived by his sons Anthony Cameron, Gavin and St. John Anthony; his daughters Susan Wildman, Justine O’Reilly and Caroline Dempsey; and 23 grandchildren.

In 2018, Mr. O’Reilly addressed friends and former teammates who had gathered in his honor at the Old Belvedere Rugby Club in Dublin.

“You win and you lose,” he said, “and if you don’t know how to lose, you don’t know how to live.”