Singapore’s founding prime minister, Lee Kuan Yew, died early Monday, leaving the wealthy and orderly city-state in uncharted territory as a small but growing percentage of the country questions the one-party monolith that Lee helped forge.

Lee, who died at 91 after a bout with pneumonia, ruled Singapore for 31 years and transforming it from a British outpost into an independent trading and finance powerhouse. Lee stepped down as prime minister in 1990 and left government in 2011, but he remained a towering figure whose distaste for corruption and criticism set the tone for modern-day Singapore.

His death brings Singapore to a moment of both grief and national anxiety. Among the central questions is whether Singaporeans — particularly a more outspoken younger generation, influenced by democratization movements elsewhere and facing slowing economic growth and rising inequality — will continue to accept what for decades has been a national paradox: economic liberty but little freedom of expression.

Singapore has been governed since its founding by the People’s Action Party. The current prime minister, Lee Hsien Loong, is Lee Kuan Yew’s son. The system is nominally democratic, but the PAP has overwhelming influence over the media and judiciary and has gerrymandered districts to give it an electoral edge.In the 2011 election, the party faired poorly — by its standards of dominance — with a fragmented opposition grabbing 40 percent of the vote.

Lee Hsein Loong said in an interview with Singaporean journalists this year that there was “no certainty” the dominance of one party would continue. “You make one small change — the [political] sky can change,” he said.“And that is not a comfortable position to be in.”


[Read: Singapore tries to imagine a future without its founder, Lee Kuan Yew]

In a statement, President Obama said of the elder Lee, “A visionary who led his country from Singapore’s independence in 1965 to build one of the most prosperous countries in the world today, he was a devoted public servant and a remarkable leader.”

Early Monday, a stream of grieving messages grew on the official Facebook page of the prime minister’s office. Nearly all were admiring.

“You have done Singapore proud,” one post said. “A tiny red dot [on the map] becomes world famous because of you.”

But others have mixed feelings about Lee’s legacy. Commentator Carlton Tan, 28, wrote in a recent column that Singaporeans “simultaneously love and hate, respect and despise, cherish and abhor, the man.”

“We are thankful for our decades of economic progress, but we wonder whether it was really necessary to sacrifice our freedoms,” Tan continued. “We are grateful for the stability and security, but we wonder whether we can maintain it without a strong civil society.”

“We are thankful for our decades of economic progress, but we wonder whether it was really necessary to sacrifice our freedoms,” Tan continued. “We are grateful for the stability and security, but we wonder whether we can maintain it without a strong civil society.”

Phil Robertson, the deputy Asia director of Human Rights Watch, said that while the economic development Lee oversaw is “beyond doubt,” it came at a “significant cost,” with restrictions and self-censorship that “Singapore now needs to overcome.”

Now that Lee Kuan Yew has passed from the scene,” Robertson wrote, “perhaps that long overdue conversation [about political liberalization] can finally proceed.”

Singapore is only about three times the size of Washington D.C., and has maintained relative peace despite its mish-mash of ethnicities and proximity to traditional powers. The country maintains close trade and defense ties to the U.S., and Singapore has spoke favorably about the Obama Administration’s avowed pivot toward Asia.

Now that Lee Kuan Yew has passed from the scene,” Robertson wrote, “perhaps that long overdue conversation [about political liberalization] can finally proceed.”

Singapore is only about three times the size of Washington D.C., and has maintained relative peace despite its mish-mash of ethnicities and proximity to traditional powers. The country maintains close trade and defense ties to the U.S., and Singapore has spoke favorably about the Obama Administration’s avowed pivot toward Asia.