Stanley Ho, the opportunistic casino tycoon who led the transformation of the tiny territory of Macau off the coast of China into the world’s most lucrative destination, died on Tuesday in Hong Kong, his family said. He was 98 years old.

In building his multibillion-dollar empire, Mr. Ho sometimes fought and more often negotiated and collaborated with the powers who threatened to defeat him, including the Japanese who occupied his homeland during World War II, the Chinese criminal gangs known as triads, the Communist government on mainland China and the United States entrepreneurs who sought to turn Macau into “Asia’s Las Vegas.”

Mr. Ho, who exploited China’s reputation for producing the world’s most passionate gamblers, amassed a family fortune that Bloomberg estimated at more than $12 billion in 2017. Operating or owning 20 casinos and related businesses, he employed a quarter of the labor force in Macau, a small city a short ferry ride from Hong Kong. For years, his enterprises accounted for over 70 percent of Macau’s tax revenue, and even financed a fleet of hydrofoils to carry gamblers to the former Portuguese colony.

Like many Chinese entrepreneurs, Mr. Ho, a father of 17, also personified the potential pitfalls faced by lucrative family-controlled businesses toward the end of their founders’ lives. His final years were marked by bitter, public bickering among his 14 surviving children from four wives, many of whom tried to push him aside and claim stakes in his empire.

In early 2011, while Mr. Ho was recovering from brain surgery, the families of his second and third wives fought for control of his business. His lawyer asserted that the ailing patriarch’s relatives had duped him into signing over his remaining shares. When Mr. Ho regained his strength, his relatives backed off and made public amends.

Throughout his life, Mr. Ho proved resilient.

“He’s the kind of guy who won’t accept defeat,” Ricardo Pinto, the publisher of Macau Closer magazine, told The New York Times in a 2007 interview. In a rare interview, with The Closer in 2007, Mr. Ho asserted: “I love challenges and never accept the answer ‘no’ easily.”

Stanley Ho Hung Sun was born on Nov. 25, 1921, into a prominent Hong Kong family whose fortune collapsed during the global depression. His grandfather was a comprador, or business intermediary, for Jardine Matheson, the British trading house, in its dealings between China and colonial Hong Kong.

His father, a comprador for Sassoon, another powerful British trading house, went broke during the 1930s and moved to Southeast Asia, leaving his family behind in poverty. Then, in 1941, the Japanese occupied Hong Kong, forcing young Stanley to drop out of college and flee with other refugees to Macau.

In Macau, Mr. Ho was hired as a clerk by a Japanese-owned import-export firm. His employers were so impressed by his business instincts that they made him a partner in 1943 at age 22.

According to “Asian Godfathers: Money and Power in Hong Kong and Southeast Asia,” a 2007 book by Joe Studwell, Mr. Ho made his first fortune smuggling luxury goods into the Chinese mainland during World War II while collaborating with the Japanese. Mr. Ho would later claim that the Japanese partly paid him in foodstuffs, which he distributed to Macau’s starving inhabitants.

But he used much of the proceeds from his wartime smuggling to start a construction company, which reaped a fortune in the war’s aftermath when Hong Kong experienced a building boom.

Mr. Ho began to make his mark as a industry giant in the early 1960s. He formed part of an investor group that won the exclusive right to run casinos in Macau by promising the Portuguese colonial authorities that it would promote tourism and improve its infrastructure. In 1961, the monopoly was named Sociedade de Turismo e Diversões de Macau, and its flagship, the Lisboa Casino Hotel, soon gained international renown.

STDM’s fortunes rocketed in the 1980s when a new capitalist class emerged in mainland China, eager to spend its wealth in Mr. Ho’s growing casinos. He devised a profitable strategy that involved subcontracting V.I.P. rooms; Mr. Ho and the subcontractors, who lured Asian high rollers to Macau, shared the revenues.

But his hotels and casinos also gained a reputation for sleaze, attracting members of notorious triads, or gangs, along with prostitutes. Law enforcement officials and analysts around the world alleged that Mr. Ho’s casinos, especially the V.I.P. rooms, were used by triads to launder their earnings from illegal enterprises.

In a written statement to The New York Times in 2007, Mr. Ho did not deny those allegations, and he pointed out that during the 1980s and 1990s “anyone involved in gaming was vulnerable to such accusations.”

But as Portugal’s 442-year colonial rule over Macau neared an end in 1999, there was a surge of triad gunfights and stabbings over control of the island’s casinos, threatening Mr. Ho’s empire and Macau’s ability to continue drawing gamblers and tourists. The violence ended with the arrival of mainland Chinese government security forces.

Mr. Ho’s monopoly came to a close in 2002, as the Beijing authorities ordered an opening of Macau to competition from foreign casino companies. Powerful operators from the United States like Steve Wynn and Sheldon G. Adelson opened billion-dollar palaces with cabarets, restaurants and five-star hotels.

Only the infirmities of advancing age slowed Mr. Ho down and made him vulnerable to his most dangerous rivals — his own family factions. After a fall at his home in 2009, he was hospitalized for seven months.

In June 2018, at age 96, Mr. Ho retired as chairman of SJM Holdings, the flagship arm of STDM, passing the reins to his daughter Daisy Ho.

His son, Lawrence Ho, became chief executive officer of Melco Crown Entertainment, a Macau casino joint venture deal that his father negotiated, also in 2007, with Crown Limited, one of Australia’s biggest and entertainment companies.

Elaine Yu contributed reporting from Hong Kong.

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