Singapore’s Riches Grew Under Its Leader. So Did Discontent.

Singapore was once known as an affluent and strait-laced city-state. Today, it’s a glitzy international destination. It has hosted Taylor Swift concerts and Formula One night races. And it is substantially richer, per capita, than the United States.

That transformation happened under Lee Hsien Loong, the Southeast Asian country’s third prime minister. He made Singapore even more prosperous by largely following the semi-authoritarian and free-market model pioneered by his father, Lee Kuan Yew, the country’s first leader.

On Wednesday, Singapore gets a new leader for the first time in nearly 20 years. Mr. Lee, 72, is handing the office to his deputy, Lawrence Wong, 51. Their People’s Action Party has governed Singapore continuously for over six decades, and has had astounding successes. But there are concerns that the vaunted “Singapore model” is failing more and more people.

Singapore is one of the most expensive cities in the world, but it does not have a minimum wage. Housing prices have surged, and many Singaporeans say social mobility has dropped considerably. Others complain that freedom of expression is still tightly controlled, if less so than before. The strains are exacerbated by the need for overseas workers; about 40 percent of Singapore’s nearly six million people are not citizens.

Compared to his famously strict father, Mr. Lee showed flexibility and responsiveness to the public’s demands, but the P.A.P.’s popularity took a significant hit during his tenure. Nonetheless it remains, for now, firmly ensconced in power.

Mr. Wong has tried to project an everyman image: He was raised in public housing, did not attend the same elite schools as his predecessors, and loves playing the guitar. Mr. Lee will stay on as “senior minister,” as his father did after stepping down in 1990. Mr. Lee has said that his children are not interested in entering politics.

Earlier this month, Mr. Lee gave his last major address to the nation at an icon of the new Singapore, the Marina Bay Sands casino resort.

“When I was sworn in as P.M., I promised to build a more inclusive Singapore: one where it is not every man for himself, but everyone working together to make things better for all of us,” he said.

A few hours later, a scene unfolded nearby that would have been unimaginable a few decades earlier. Hundreds had gathered for a rally at Speakers’ Corner, the one place in the city-state where Singaporeans can protest without a permit. Among them were delivery workers, bus drivers and health care workers, and many wore fluorescent yellow safety vests, evoking a French anti-government movement.

Addressing the crowd, Kokila Annamalai, an activist, said the P.A.P.-led government had built systems that “have always protected the wealthy, not the working class.” Singapore, she added, is “a playground for the rich while the poor are squeezed into tiny rental flats.”

The P.A.P. is one of the world’s most dominant political parties. Its ministers are paid high salaries, which the party says prevents corruption. It transformed Singapore from a backwater swamp into a first-world nation and a key cog in global maritime trade. Gross domestic product is about $83,000 per capita, compared with roughly $76,000 in the United States. The city-state, a major financial hub, deftly managed the coronavirus pandemic and rising tensions between the United States and China.

But discontent has been growing. In the 2020 election, the P.A.P.’s share of the popular vote reached a new low of 61 percent, and the opposition won a record 10 seats in Parliament, out of 93 that were up for grabs.

Choo Yi Hung, 30, has never voted for Mr. Lee’s party. Two years after graduating from college with a degree in English language and linguistics, he delivers food and tutors students, making about $2,400 per month. He still lives with his parents; he would like his own apartment, but that is out of reach. He can’t buy a public housing flat from the government until he gets married or turns 35. Not that he can afford one.

Mr. Choo contrasts his predicament with that of his grandmother, who raised five children in the 1960s as an uneducated widow. Her descendants now have lifestyles that he described as “comfortably middle class,” with some owning condominiums and cars.

“I guess a lot of people will say: ‘Yeah, you grew up in a more developed country, a wealthier country,’” Mr. Choo said. “But I would argue that the opportunities for social mobility are far, far less.”

Mr. Lee once said that a two-party political system was “not workable” in Singapore. But in 2020, he formally established the position of opposition leader in Parliament and made concessions that allowed the opposition bloc to control 12 seats, more than the 10 it had won.

“He knew that if he wanted to maintain P.A.P.’s dominance — which I think he has largely done — he had to manage the pace of change,” said Eugene Tan, an associate professor of law at Singapore Management University.

On the social front, perhaps the most sweeping change that Mr. Lee made was repealing a colonial-era law that banned consensual sex between men.

“At least there’s a sense of ‘We can do this now,’ and that ultimately we are not criminals anymore,” said Leow Yangfa, the executive director of Oogachaga, an L.G.B.T.Q. rights group.

But Mr. Lee also moved to cement the definition of marriage as a heterosexual concept. Public discussion of race and religion remains tightly controlled, and rights groups say the government is still combative with its critics. In 2021, Singapore’s High Court ordered a blogger to pay Mr. Lee about $100,000 for defamation. (The New York Times Company apologized and paid fines in 2010 and in the mid-1990s to settle libel claims brought by Singaporean officials over opinion articles.)

Critics say the government has weaponized a law it says was designed to combat fake news.

“You never know when or what you’re going to say is going to run afoul of the authorities,” said Joel Tan, a playwright and podcaster.

In a statement, the Singapore government said it had increased engagement with the public. It also laid out its philosophy on free speech.

“Freedom of expression is an important part of Singapore’s constitution, but it does not confer on Singaporeans an unqualified right,” the statement said. “In situations where it affects the safety and security of people in Singapore, and the peace and harmony that Singapore enjoys, the government does and will intervene.”

For some, Mr. Wong’s appointment is encouraging.

“We don’t have a Lee anymore, but we also have a nontraditional type of leader,” said Sudhir Thomas Vadaketh, the editor in chief of Jom, an independent online magazine about Singapore. “I do like that.”

In recent years, Mr. Lee had to contend with a public feud with his siblings and a series of scandals within the P.A.P. that sullied the squeaky-clean image the party projects. But he leaves office as a popular leader.

Zoe Tan recalled seeing Mr. Lee mingling with residents in Teck Ghee, a district in northern Singapore. “He’ll walk the market and is very humble,” Ms. Tan said. “He will take pictures with us.”

On two separate occasions, Ms. Tan said, she emailed the prime minister to ask for a grace period for housing payments. Both times, his office made quick arrangements to help her.

“I feel very sad Lee Hsien Loong is going to retire, I thought he was going to continue forever,” said Ms. Tan, who now works for Singapore’s Community Development Council.

In his speech at Marina Bay Sands, Mr. Lee suggested that political change could threaten Singapore’s prosperity.

“The system does not have to fail outright for Singapore to get into trouble,” he said. “If our politics becomes like other countries, we will end up worse than other countries.”