The "Good Guy" Director !?
Transcript So, on one side of a narrow causeway in the mid-1960s, you had chaos: riots in the streets, racial violence, and a struggling former colony trying to figure out what it even was anymore.
On the other side of that causeway, something strange was happening. A mosquito-infested trading post was transforming into something that definitely shouldn’t have been possible. Housing blocks marched to the horizon, factories hummed with foreign investment, and streets became so clean you could practically eat off them — though you’d probably get fined for trying. And also, don’t be a weirdo.
At the center of it all stood a thin man in white with the voice of a drill sergeant: Lee Kuan Yew. He promised to drag his tiny island from “third world to first.” And he did it.
When Singapore became independent in 1965, GDP per capita sat around $500. By the time Lee died in 2015, it was over $55,000 — a hundredfold increase in 50 years.
But a few kilometers away from those spotless streets, behind the walls of detention centers, other Singaporeans sat on concrete floors. Some were held for years, even decades, without trial or formal charges — just a minister’s signature and the label “security threat.” Their names rarely appeared in the miracle narrative, and when they did, it was usually as villains.
So, did Lee Kuan Yew save Singapore because he ruled like a dictator? Or did Singapore succeed despite the price people paid? Let’s find out.
The phrase “benevolent dictator” gets thrown around a lot, usually as a thought experiment. What if you had a leader who was smart, incorruptible, genuinely wanted the best for his people, and also had absolute power to make it happen? No messy coalitions, no gridlock, no pandering to special interests — just a wise ruler making wise decisions without interference.
Sounds nice. Mostly fantasy, of course. “Absolute power corrupts absolutely” and all that. It’s the kind of debate people have in philosophy seminars or Reddit threads at 2 a.m. But when people argue that it might actually work in the real world, they almost always point to the same example: Singapore.
Lee never called himself a dictator. Technically, he was a prime minister in a parliamentary democracy, elected and reelected for over three decades. But the label stuck because he governed like one.
Lee ran Singapore the way a strict headmaster runs a boarding school: rules for everything, consequences for breaking them, and absolutely no doubt about who was in charge.
Western observers found this fascinating. Here was an Asian leader who spoke perfect English, quoted Shakespeare, debated economic policy with Milton Friedman, and delivered results that made many democracies look sluggish. Friedman praised Singapore as a triumph of free-market economics. Other economists held it up as proof that development could skip the messy parts if the right person was in charge.
When Lee died in March 2015, tributes poured in. Barack Obama called him “a true giant of history.” Tony Blair, Henry Kissinger, and leaders across the political spectrum praised his vision. The Economist ran a lengthy obituary calling him “the wise man of the East,” though it acknowledged — almost as an aside — that his methods wouldn’t pass in most Western democracies.
But while those glowing tributes were being written, human rights organizations were telling a different story. Freedom House rated Singapore only “partly free” for decades. Human Rights Watch documented restrictions on speech, assembly, and political opposition. Amnesty International criticized the country’s use of detention without trial since the 1970s.
So Singapore became this strange case study: hailed both as a model of good governance and as an example of systematic rights violations, depending on who you asked.
The question isn’t really whether both things are true. They clearly are. The real question is whether they’re connected — whether Singapore succeeded because of authoritarianism or despite it.
To understand why so many Singaporeans accepted Lee’s style of governance, you have to understand what came before it — and what came before it was not good.
Picture Singapore in the 1950s: a British colonial port crammed onto an island about half the size of London, with a million people packed into shophouses and makeshift kampongs built from wood and zinc sheets. Sanitation was poor. Tuberculosis was everywhere. In some neighborhoods, dozens of people shared a single water tap.
Then there were the secret societies — criminal gangs controlling large parts of the informal economy through protection rackets, gambling dens, and prostitution. Labor unrest was constant. Communist-influenced unions organized strikes that could shut down the entire port for days.
The British, who had ruled Singapore since 1819, were beginning to wonder whether the colony was more trouble than it was worth.
On top of all that came ethnic tensions. Singapore’s population was roughly three-quarters Chinese, with significant Malay and Indian minorities. The British had spent decades governing through divide-and-rule policies, keeping communities largely separate: different languages, schools, and neighborhoods.
When tensions flared, things escalated fast.
In 1950, riots broke out after a custody dispute involving a Dutch Muslim girl named Maria Hertogh. Eighteen people died and 170 were injured. More riots, strikes, and communal violence followed throughout the decade.
By 1959, Britain granted Singapore internal self-government. The island gained its own elected prime minister and responsibility for domestic affairs, though defense and foreign policy remained under British control.
The plan was eventually to merge with the Federation of Malaya. Singapore would gain access to a larger market, natural resources, and a security umbrella. In 1963, it happened. Singapore joined Malaysia.
It lasted barely two years.
Tensions between Singapore’s Chinese majority and the Malay-dominated federal government in Kuala Lumpur escalated rapidly. Race riots in 1964 left dozens dead. Eventually, Malaysia’s leadership concluded Singapore was more liability than asset.
On August 9, 1965, Singapore was expelled from Malaysia and suddenly became independent whether it wanted to be or not.
Lee Kuan Yew, who had championed the merger and genuinely believed Singapore could not survive alone, wept on national television.
Singapore had no army, no natural resources, and not even enough fresh water. It was a tiny island suddenly expected to survive as a sovereign state.
This was the backdrop for Lee’s argument in favor of strong centralized government. Soft, consultative leadership might work in stable, prosperous democracies. Singapore in 1965 was none of those things.
One economic collapse, one outbreak of communal violence, one major mistake, and the whole experiment could fail.
Whether that justified everything that came afterward is another matter entirely. But it explains why so many people were willing to give Lee the benefit of the doubt.
Lee Kuan Yew was born on September 16, 1923, into a prosperous Straits Chinese family. His grandfather made money in shipping. His father worked for Shell. Young “Harry,” as his English-educated family called him, grew up speaking English at home and attended Raffles Institution, the island’s most prestigious school.
Then came World War II.
When Japanese forces captured Singapore in February 1942, Lee was 18 years old. The occupation lasted three and a half years and left a permanent mark on him. He witnessed arbitrary violence, worked for a Japanese news agency to survive, and learned how absolute power operated.
Later, Lee would repeatedly point to this experience. The British had promised to defend Singapore — and surrendered in a week. You couldn’t rely on anyone else.
After the war, Lee studied law at Cambridge, graduating with a rare starred first. There he met Kwa Geok Choo, another Singaporean law student who became his wife and lifelong confidante.
Returning to Singapore in 1950, Lee began representing trade unions. Many unions were dominated by Chinese-educated workers with leftist sympathies. This was politically smart. The English-speaking elite were tiny. The real political energy came from Chinese-speaking workers drawn toward socialism and communism.
Lee himself didn’t initially speak Mandarin or Hokkien fluently, but he learned quickly and became useful to union leaders who needed someone capable of arguing their cases in English courts.
In 1954, Lee and several allies founded the People’s Action Party (PAP), a broad anti-colonial coalition uniting English-educated moderates and Chinese-educated radicals.
The moderates provided legitimacy. The radicals provided grassroots support.
Both sides distrusted each other.
Interestingly, during this period Lee strongly opposed the colonial government’s practice of detaining suspected subversives without trial. He denounced it as unjust colonial oppression and defended detainees in court.
That detail becomes important later.
The PAP swept the 1959 elections, and Lee became prime minister at just 35 years old. But tensions inside the party were already becoming unmanageable.
Lee wanted to neutralize the left wing before it could neutralize him. The merger with Malaysia offered the perfect opportunity. Within a larger, more conservative federation, Singapore’s communists and leftists would be politically weakened.
The radicals opposed the merger for exactly that reason.
What followed shaped Singapore’s political future for decades.
In the early morning hours of February 2, 1963, police and security officers swept across Singapore arresting 113 people: union leaders, journalists, student activists, opposition politicians, and former allies of Lee who had drifted too far left.
This became known as Operation Coldstore.
The government claimed the detainees were communist operatives attempting to sabotage the merger with Malaysia. Officials described it as a preemptive strike to defend democracy.
And context mattered. It was the height of the Cold War. Communist insurgencies existed throughout Southeast Asia. Many people accepted the government’s justification.
But many detainees were not communists. Some were trade unionists, social democrats, and left-leaning nationalists who simply opposed Lee politically.
The most prominent was Lim Chin Siong, once one of Lee’s closest allies and arguably more popular among Chinese-speaking voters than Lee himself.
The detainees were held under emergency security laws: no trial, no formal charges, no requirement for evidence to be publicly presented. Some remained imprisoned for years.
The irony was striking. When the British used these powers, Lee condemned them as unjust. Once he controlled them, he defended them.
Historians still debate Operation Coldstore. The Singaporean government maintains it targeted genuine threats. Critics and revisionist scholars argue it primarily eliminated political opposition before elections.
What is undisputed is the outcome. After Coldstore, the PAP faced no meaningful opposition from the left. Opposition networks were shattered. Leaders were imprisoned or exiled.
In Singapore’s first post-independence election in 1968, the PAP won every seat.
And the legal framework that enabled Coldstore didn’t disappear. It evolved into the Internal Security Act (ISA), which granted the government broad powers to detain individuals indefinitely without trial.
Critics would later call this the foundation of Singapore’s security state.
Yet this is where Singapore becomes genuinely unusual among authoritarian systems: the government actually delivered results.
Many dictators promise prosperity. Most enrich themselves instead.
Lee Kuan Yew approached economic development with relentless pragmatism. Singapore lacked natural resources, agricultural land, and even a meaningful domestic market. So Lee turned those weaknesses into selling points.
Foreign corporations were promised political stability, low taxes, educated workers, efficient bureaucracy, and reliable courts.
And the strategy worked.
By the late 1960s, foreign investment was pouring into Singapore. Unemployment fell rapidly.
Crucially, Lee also prioritized anti-corruption efforts. Civil servants were paid extremely well to reduce incentives for bribery. The Corrupt Practices Investigation Bureau gained sweeping investigative powers, including authority to investigate ministers and their families.
When officials took bribes, they went to prison.
The result was a state bureaucracy that actually functioned.
Singapore consistently ranks among the least corrupt countries in the world. Policies were implemented efficiently rather than weakened by corruption and patronage.
Lee described himself as ideology-free. If something worked, he used it. State-owned companies existed but competed internationally. Healthcare combined subsidies, forced savings, and market mechanisms. Education prioritized English and technical skills.
If a policy failed, it was changed.
For millions of Singaporeans, the transformation was extraordinary. Families moved from kampongs into modern apartments. Poverty declined dramatically. Entire generations experienced upward mobility within a single lifetime.
That explains why so many Singaporeans still speak about Lee with genuine admiration.
One of the government’s largest achievements was public housing.
In 1960, the Housing and Development Board (HDB) was created to address Singapore’s housing crisis. The colonial government had built around 23,000 public housing units in three decades. The HDB built more than that in its first three years.
By the late 1980s, over 80% of Singaporeans lived in HDB apartments, most owning their homes through subsidized purchase schemes.
Public housing in Singapore became the norm rather than a last resort.
The government also introduced the Ethnic Integration Policy in 1989. Housing blocks were assigned racial quotas for Chinese, Malay, and Indian residents to prevent ethnic enclaves.
Supporters argue the policy helped preserve social harmony. Critics note it can disadvantage minorities financially by limiting who can buy their apartments.
Housing policy was only one part of a much broader effort to shape public behavior.
The government launched campaigns against littering, spitting, chewing gum, and even “Singlish.” Men with long hair were discouraged. Family planning policies shifted from “Stop at Two” in the 1970s to encouraging educated women to have more children in the 1980s.
Some policies produced obvious benefits. Singapore became one of the cleanest cities in the world.
Others became international punchlines, especially the chewing gum ban.
But beneath all of it was a deeper governing philosophy: the state should actively shape society.
The Internal Security Act remained central to that philosophy.
Although originally justified as protection against communist threats, the ISA survived long after those threats faded. In the 1980s, when courts briefly attempted to increase oversight of ISA detentions, the government amended the constitution to restrict judicial review.
The law remained extraordinarily powerful not simply because of how often it was used, but because everyone knew it could be used.
That atmosphere mattered.
In 1987, another major security crackdown occurred: Operation Spectrum.
The government announced it had uncovered a Marxist conspiracy to overthrow the state. Twenty-two people were arrested under the ISA, including social workers, Catholic activists, theater practitioners, and professionals involved in civil society organizations.
State television aired confessions from detainees.
Later, several detainees claimed their confessions were coerced through psychological pressure and sleep deprivation. When some publicly retracted their confessions, several were rearrested immediately.
Human rights groups and international legal organizations challenged the government’s narrative, arguing there was little evidence of an actual conspiracy.
The government never backed down from its position.
Regardless of the truth, the political effect was clear. Civil society organizations became dramatically more cautious. Lawyers, academics, activists, and religious organizations all pulled back.
Lee understood something many authoritarian rulers miss: you don’t need to arrest thousands of people to reshape a society. You only need to arrest enough prominent people to send a message.
Singapore still held elections, and they were technically competitive. Opposition parties existed. Voting was genuine.
But the PAP dominated every election after 1959.
Part of that dominance came from genuine public support. Many Singaporeans voted PAP because they believed the government had improved their lives.
But structural advantages also mattered.
Group Representation Constituencies (GRCs), introduced in 1988, required opposition parties to field entire teams of candidates rather than individuals, significantly increasing campaign costs and barriers to entry.
Electoral boundaries were frequently redrawn by the government.
Media outlets were closely tied to the state or state-linked companies.
And defamation lawsuits became a powerful political weapon.
Opposition politicians who accused ministers of wrongdoing often found themselves sued for enormous sums. Some were bankrupted and barred from running for office.
Critics argued this created a chilling effect throughout society.
Supporters countered that Singapore simply maintained stricter standards against false accusations.
The result was a democracy that functioned procedurally, but with an overwhelmingly dominant ruling party.
Beyond politics, Lee also shaped Singapore culturally.
English became the primary language of instruction, while ethnic “mother tongues” were taught separately. Mandarin replaced many Chinese dialects, weakening older community networks but unifying communication.
Lee also championed the concept of “Asian values,” arguing that Asian societies prioritized social harmony and collective responsibility over Western-style individualism.
Critics saw this as an ideological justification for authoritarian rule.
Singapore’s media and arts industries operated under careful regulation. Sensitive political topics often faced restrictions. The effect wasn’t necessarily overt censorship so much as widespread self-censorship.
People learned where the boundaries were.
Over time, however, new pressures emerged.
Singapore remained wealthy, safe, and efficient. But inequality increased. Competition within the education system intensified. Younger generations who never experienced the instability of the 1950s and 1960s began questioning the trade-offs their parents had accepted.
Why should economic success require strict political constraints?
Why should criticism of government officials carry such severe consequences?
These debates increasingly appeared online and in election results where opposition parties gradually gained support, even while the PAP remained dominant.
Lee stepped down as prime minister in 1990 but remained deeply influential as Senior Minister and later Minister Mentor.
In 2004, his eldest son, Lee Hsien Loong, became prime minister.
Supporters argued he earned the role through merit and experience. Critics saw dynastic politics emerging inside a system that claimed to be meritocratic.
After Lee Kuan Yew’s death in 2015, a public feud erupted within his family over his home at 38 Oxley Road. Lee reportedly wanted the house demolished to avoid turning it into a political shrine.
His children publicly accused one another of abusing political influence.
The dispute damaged the carefully cultivated image of a unified, selfless ruling elite.
And that leaves the central question.
Lee Kuan Yew undeniably transformed Singapore. He built one of the safest, least corrupt, and most prosperous societies in the world from extraordinarily fragile beginnings.
But the costs were real too: detention without trial, limited political competition, constrained press freedom, and a culture shaped heavily by state control.
The Singapore model worked under unusually specific conditions: a small population, competent institutions, and a leader more focused on national development than personal enrichment.
Most authoritarian leaders who invoke Lee imitate the repression without reproducing the competence.
And perhaps the deeper issue is that authoritarian systems depend heavily on who holds power. Singapore was fortunate in many ways.
But fortune is not a political system.
The miracle Singaporeans could see clearly: clean streets, economic growth, safety, prosperity.
What they couldn’t easily see were the alternatives that never fully emerged — because many of the people who might have offered different visions were imprisoned, exiled, bankrupted, or too afraid to speak.
Thank you for watching.
