Lee Kuan Yew brought prosperity to Singapore with an authoritarian system designed to outlast him, but that legacy may be ill-suited for the 21st-century challenges facing the tropical city-state.

One of the last of a generation of Southeast Asian strongmen, Lee died Monday at age 91 after being hospitalized in early February, suffering from severe pneumonia. The famously blunt-speaking autocrat stepped down as prime minister in 1990, but for decades after remained a commanding presence in Singapore politics and the region. His son is the current prime minister.

His death is an inflection point for Singapore. After gaining self-rule from Britain in 1959, the island at the tip of the Malay Peninsula was transformed under Lee's iron leadership into a wealthy finance and manufacturing powerhouse.

To give his government a free hand to fashion a new society, Lee systematically crushed dissent, muzzled the press and imprisoned political opponents. A social compact of authoritarian government in exchange for a guarantee of prosperity has endured for two generations.

Now, it is increasingly under strain.

Singaporeans prize the pluses such as low crime, harmony between the Chinese majority and Malay Muslim minority and almost zero corruption in a region where graft is rampant. But an increasing number fret that the ruling party has pushed their country of 5.4 million in the wrong direction in the past two decades. Income inequality has soared and large-scale immigration has increased competition for jobs and depressed wages. Destitute elderly Singaporeans pushing carts along the city's immaculate streets, collecting cardboard and plastic that they sell to recyclers, are vivid evidence of the gaping holes in its social safety net.

"There's dissatisfaction, you can feel it, and people are stirring for change," said Lynn Su-lin, a 56-year-old business owner. She is of a generation that hails Lee's achievements as "amazing" and worries younger Singaporeans don't fully appreciate their inheritance. Without Lee, "we're a bit frightened of what will happen."

The ruling party suffered a stinging setback in 2011 elections. By the standards of Western democracies it was an overwhelming victory, but the People's Action Party's share of the vote fell and the tiny opposition picked up seats. In response, the government has doled out more social welfare in recent budgets and slowed immigration, but the changes may not yet be bold or fast enough to placate an increasingly vocal electorate.

"The idea that people only vote for the opposition when they are desperate is no longer true, if it ever was true," said Garry Rodan, a Southeast Asia expert at Murdoch University in Perth, Australia. "Some of the last budget measures may not have come without opposition gains in elections."

Singapore, said Yeoh Lam Keong, a former chief economist of Singapore's sovereign wealth fund GIC, is being buffeted economically and politically by "huge transformative forces."

Like other developed countries, it is facing the pains of globalization. New technology is displacing middle- and working-class jobs and competition from the vast labor forces of China and India is holding down wages. At the same time, a well-educated and Internet-connected generation of young Singaporeans with high expectations has reached voting age. In Asia, that generation's aspirations were underlined by last year's student-led pro-democracy protests in Hong Kong that shut down parts of the city for weeks.

"I respect Lee Kuan Yew for his contributions to building our nation yet disagree with some of the things he has done," said 22-year-old university student Tan Guan Hong. "I hope we take a step back. I hope that the future opens up opportunities to revisit the problems."

The Singapore government has strong fiscal resources and with a moderate increase in its ultra-low tax rates can afford to markedly boost social spending in a sustainable way, Yeoh said. But compromising with Singaporeans who want less top-down rule and a greater say in their own lives will be its more profound challenge.

"Democratization is the trickier part because Lee Kuan Yew's legacy is also benevolent authoritarianism," he said. "They are standing against the tide in the long run, 10 to 20 years. They really need to lead that rather than get dragged along by it. I'm not sure if they have the inclination to do that."

Under the current prime minister, Lee's son Lee Hsien Loong, the government has maintained control over the media, tried to stifle online criticism and kept Speakers' Corner, a small park, as the only location in Singapore where protests can be held.

In his heyday, Lee Kuan Yew reinforced his hold on power with dire and widely believed predictions that all of Singapore's progress could be undone and the country hurled back into the developing world if voters opted for the opposition.

In reality, and unlike the "From Third World to First" title of Lee's memoirs, Singapore never knew grim poverty. Before independence, it was by the standards of the region a prosperous commercial hub of the British Empire.

Yet after its split in 1965 from a short-lived and acrimonious federation with Malaysia, Singapore's future was highly uncertain. It lacked natural resources, having to import even water, and was surrounded by hostile neighbors. In control of all policy levers, Lee and his government obliterated independent trade unions, reconfigured the education system to produce workers that met the needs of foreign investors and pushed through other changes to make the island competitive. Whenever the economic model faded, a new plan would be announced and implemented in sweeping fashion.

Today, its GDP is among the highest in the world at $54,000 per head, according to the World Bank, and it consistently ranks at the top of surveys of competiveness, while Malaysia and other Southeast Asian nations lag far behind.

But even that remarkable success has produced its discontents.

"My big grouse about Singaporeans is that they're so obsessed about money and getting ahead that they've lost their humanity," said Su-lin, the businesswoman. "They admire success so much that there's no room for people who don't want to chase all those dreams."

And nowadays, predictions of economic demise from a greater opposition role in politics are not as easily believed.

"The worst-case scenario for Singapore economically is being the No. 10 city instead of the No. 1 city or No. 2 in Asia," said Cherian George, a Singaporean academic and commentator who now lives in Hong Kong. "But it would still be prosperous."

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AP writer Jeanette Tan contributed to this report.

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