“No substantial famine has ever occurred in any independent country with a democratic form of government and a relatively free press.”
​
— Amartya Sen, Development as Freedom (1999)
​
Sen—a Nobel Prize–winning economist from India—helped transform the way the world thinks about development. His insight was simple yet profound: political freedom is not just a moral good, it is an economic necessity. Without free debate and accountability, governments can ignore their people’s most basic needs. With political freedom, citizens gain the power to demand competence — and that’s what makes broad prosperity possible.
​
That idea has long shaped my own political philosophy. For decades, I’ve argued that people cannot flourish without liberty in both markets and governance — because over the long run, one without the other always collapses.
​
And yet, looming over Sen’s insight is a glittering contradiction: Singapore.
​
Here is a tiny island nation with some of the highest living standards on Earth—a global financial powerhouse—where gleaming skyscrapers rise from what was once swamp and jungle. It thrives without the freedoms we instinctively associate with prosperity. Speech is restricted. Press is muzzled. Political opposition is allowed only on a short leash: as when opposition leader Chee Soon Juan was repeatedly jailed and bankrupted for his peaceful opposition.
​
And yet, the economy hums with efficiency and order.
​
How can this be?

The Founding Father

Singapore’s paradox is this: prosperity has been built with economic freedom, but without democracy. What makes Singapore exceptional is its choice to embrace economic liberty—low taxes, free trade, openness to global markets—while crushing political dissent.
The story begins with one man: Lee Kuan Yew, Singapore’s brilliant founding father, who became prime minister in 1959 when Britain granted the island self-governance. At the time, Singapore was a poor, divided trading post with no natural resources to rely on. In 1963, Lee led the country into a merger with newly independent Malaysia, only to be expelled two years later after bitter political and ethnic clashes.
​
Suddenly, in 1965, Singapore found itself a tiny, vulnerable city-state, thrust into full independence almost by accident. In that moment of crisis, Lee’s determination and vision took center stage. Over the next three decades, he built institutions from scratch, enforced the rule of law, crushed corruption, and transformed a struggling backwater into a thriving global hub.
​
The People’s Action Party (PAP), which Lee led, became the sole force in politics — but unlike most one-party regimes, it remained astonishingly disciplined. Where other dictators nationalized and meddled, Singapore’s leaders let markets function. They kept their grip on politics iron-tight without strangling the economy. That rare self-restraint explains much of Singapore’s success.

Singapore's Astonishing Consistency

Since Lee, Singapore has had only two prime ministers — Goh Chok Tong (1990–2004) and Lee Hsien Loong (2004–present), Lee’s own son. Three leaders in 66 years, all from the same party, all chosen from the same succession line, all consistently practicing the same free-market principles. In truth, the elder Lee’s shadow never lifted; he served as “Senior Minister” and later “Minister Mentor,” shaping policy until his death in 2015.
​
That tiny sample of leaders matters. We do not know how Singapore’s system will endure without the lineage of leaders tied to Lee’s legacy. Without genuine competition, the danger is always there: that one day, the ruling party may put its own survival above economic efficiency. That’s the Hayekian trap — the danger that centralized political power will, sooner or later, politicize the economy and choke the very freedoms that create wealth.
​
For now, Singapore prospers. Its courts remain predictable. Its government is still among the least corrupt in the world. Its ports and financial markets continue to draw global capital.
​
But cracks are emerging.

Asia’s Fiercest Tiger Grows Old

Once Asia’s fiercest “tiger economy”, Singapore now grows at a modest 1–3%—a natural slowdown for a maturing nation, yet a stark contrast to its meteoric rise. The benefits of that prosperity are pooling at the top, as inequality widens and cost of living climbs. And beneath the polished surface of wealth, a new generation—raised in affluence—is hungry for the political freedoms their parents dared not demand.
​
And the younger Lee is now in his seventies, his long tenure nearing its close. His designated successor, Lawrence Wong, will inherit the immense weight of maintaining both prosperity and political stability—but without the near-mystical authority of the founding generation.
​
That combination is vanishingly rare. Russia chose nationalism and kleptocracy. Venezuela strangled its economy with socialism. China veers away from its decades-long experiment with liberalization, tightening political control at the expense of innovation.
​
Singapore’s success is not proof that authoritarian capitalism works; it’s proof that no one else can pull it off.
​
Yet even Singapore may not escape the laws of history forever. Without open debate, free ideas, and political competition, innovation can stagnate. Centralized power always carries the temptation of interference. One generation of brilliant technocrats can make an economy soar; the next can smother it.
​
Amartya Sen was right: political freedom is not just a moral principle, but the bedrock of lasting prosperity. Singapore has dazzled the world by defying that truth for two generations — improbable, disciplined, admired.
​
But the handover to Wong will be the ultimate test—of whether Singapore’s carefully managed system can outlast the charisma and legitimacy of the family that built it.
​
If it fails, Singapore will join the long historical record proving that prosperity cannot endure without freedom—economic and political alike.

Refer a Friend:

If you've enjoyed this episode of Dispatches from the Rebellion, please consider referring a friend. Forward this email and ask them to click on the "Subscribe" button below to sign up.

​