The paper, which was co-written by Curtis Milhaupt of Stanford Law School, spells out why benevolent authoritarians have an easier time plugging their countries into the global economy. Elites tend to resist big changes that would cut into their own bottom lines, even if those changes are good for the country. Autocrats have more tools to get them on board. An autocrat’s word can convince job-creating investors that their businesses will be protected, filling the void of a shaky court system. In a benevolent autocracy, legitimacy often comes not from elections but from the ability to show material improvements in people’s lives. In a democracy, leaders are often too busy fending off political challenges to make grand economic plans. They are frequently voted out of office before they can see those plans through. To win elections, politicians make short-term promises — like cutting taxes while increasing benefits — that don’t always make economic sense in the long run.

But benevolent autocracies have fatal flaws, too. Benevolent dictators are hard to find. There’s no guarantee that they will stay benevolent or that their successors will be as competent. After a country successfully transitions its economy, the advantages of this system seem to fade. But by then, a system of nearly unchecked power at the top has become entrenched.

Singapore is a case in point. Lee Kuan Yew contended that people don’t pine for democracy. First and foremost, he said, “they want homes, medicine, jobs, schools,” according to the 1998 book “Lee Kuan Yew: The Man and His Ideas.” He provided those things by pairing business-friendly policies from the West (predictable courts, low taxes, zero tolerance for corruption and an embrace of meritocracy) with socialist-leaning policies from autocracies (heavy government involvement in economic planning and little tolerance for dissent). He created a vast system of public housing, where about 80 percent of Singaporeans currently live. People buy and resell long-term leases to government-built apartments with money the government essentially forced them to save. Singapore holds elections, but the ruling party, which controls much of the media and a host of lucrative jobs, has remained in power since independence.

Anyone who has visited the city-state of nearly six million people has seen how much cleaner and safer and more orderly it feels than the United States. Its airport doubles as a high-end mall. Public gardens bloom free of the litter, pickpockets or homeless encampments that have become familiar sights in U.S. cities. Robberies are so rare — and surveillance so pervasive — that some high-end bars don’t even lock their doors at night. Ferraris and Lamborghinis are everywhere, as if the slogan “a chicken in every pot” has turned into “a sports car in every parking space.”

But now, eight years after the death of Lee Kuan Yew, Singapore is at a crossroads. It’s being run by his eldest son, Prime Minister Lee Hsien Loong, who leans heavily on his father’s legacy. Elections for the largely ceremonial post of president are expected in September and parliamentary elections are due by 2025. The prime minister’s potential successor has already been picked. But the ruling People’s Action Party has never looked so vulnerable.

In the summer of 2017, while he was visiting his parents in Singapore, he wrote comments in a private Facebook post that criticized the government for using the courts to silence its critics. The government is “very litigious and has a pliant court system,” he wrote. Soon after, he got a tip that he was about to be prosecuted for it. He hurried back to the United States. Even during the Trump administration, which was known for its harsh treatment of immigrants, he felt relieved to land on American soil because he knew there were independent judges, he told me. He was convicted in absentia in Singapore for scandalizing the judiciary and fined $15,000, which bars him from running for Parliament for five years.

Last month, officials in Singapore announced an ongoing police investigation of Shengwu Li’s parents, who are accused of manipulating the then-90-year-old Lee Kuan Yew into changing his will and lying about it afterward. The accusation stems from a simmering disagreement over the fate of the family home, which Lee Kuan Yew said publicly at times that he wanted demolished after his death.

Lee Hsien Yang, Lee Kuan Yew’s youngest son, says he has been fighting to honor his father’s wish not to have a cult of personality built around the house. But he says his elder brother, the prime minister, wants to preserve the house as a national monument to bolster his own political legitimacy. Lee Hsien Yang spoke out publicly against his brother, only to get hit with an investigation. Eventually, he fled the country, like his son. It seems to be an example of what Kenneth Paul Tan, a Singaporean professor of cultural studies, calls the “politics of evermore sophisticated bullying.” At its core, the fight isn’t about a house or a will. It’s about the future of Singapore.

“The institutions in Singapore, whether it is the judiciary, the civil service, the army, the institutions of higher learning, have all gradually come under direct control in a way that stifles independent thinking and challenge,” Lee Hsien Yang told me. Lee Kuan Yew would solicit different views and occasionally change his mind, he said. “Today, the Singapore authorities no longer have people who would challenge the system to say, ‘Here’s my view. I don’t think you are doing the right thing.’ They are too well-paid.”

(Ho Moon Shin, a government spokesperson, denied that Lee Hsien Yang and Shengwu Li are in exile, saying they are traveling on Singaporean passports and are free to return home. She also said Prime Minister Lee Hsien Loong recused himself from the cases involving the family house.)