(Note: This blog post reflects my personal opinion at the time of writing and may evolve as I continue to learn.)
I’m planning to write a series on world politics as I see it, with each piece grounded in a specific geography: the Middle East, NATO and the EU, Eastern Europe and Russia, China, Southeast Asia, America, and so on. But I also want to spend a disproportionate amount of time zooming in on Singapore for two reasons.
First, I want outsiders to understand Singapore in a way that goes beyond the usual headlines and travel brochures. Second, I want Singapore to function as a kind of mirror. By commenting on Singapore’s stance toward certain issues, I can hint at my own stance without having to announce it outright. People who are paying attention will understand me more clearly, and those who are not will still get a useful portrait of a country that matters more than its size suggests.
This post is about Singapore, starting from a very niche angle. I have a lot of raw and unorganized thoughts, and I am going to try to arrange them into something coherent.
For those who don’t know, Lee Kuan Yew is broadly considered the “founding father” of Singapore. In 1965, Singapore separated from Malaysia and became independent, and Lee, as the then Prime Minister, undertook the task of turning a small and vulnerable island into a functioning nation with real leverage in the world. Today, Singapore is one of the most developed countries across many dimensions. Lee is widely credited as the chief architect of that transformation. He is also often described as iron-fisted, and because he was pragmatic to the point of ruthlessness when he believed it was necessary, there are criticisms that he ruled like a dictator even if he delivered outcomes many countries can only envy.
This is contextual knowledge. If you want to understand Lee more, watch his interviews. My personal impression is that he was highly educated, but more importantly, genuinely sharp in a way that is rare. He did not just build Singapore materially. He also tried to insert a certain idea into the global imagination: that small countries are not doomed to be irrelevant, that they can survive by thinking clearly, positioning intelligently, and acting decisively. And he was successful in making the world take that idea seriously.
I am not going to go further into Lee himself. What I want to talk about today is the contrast between two of his grandsons, Li Hongyi and Li Shengwu, and the very different eulogies they delivered when Lee Kuan Yew passed away. From that contrast, I want to extend into what I think I understand about Singapore.
I single these two out from the larger family not because the other descendants are unimportant, but because these two, to me, seem to have inherited some portion of Lee’s intellectual force. Hongyi was an International Physics Olympiad bronze medalist who went on to MIT. Shengwu was an award winner at the World Universities Debating Championships and went on to study PPE at Oxford and economics at Stanford. These are credentials that, to people who know those worlds, signal an uncommon level of ability. My assessment is superficial, but it is not random. In places like Singapore, credentials are not just decorations. They are signals that the system and the world can both recognize.
They are not siblings. Hongyi is the son of Lee Hsien Loong, Singapore’s former Prime Minister, who inherited the leadership baton through the dominant party’s internal political machinery and the country’s electoral reality. Shengwu is the son of Lee Hsien Yang, Loong’s brother, who has been a vocal critic of the government in recent years and aligned himself more openly with opposition politics. Shengwu himself became entangled in legal disputes after criticizing the government as “litigious” and describing the court system as “pliant” in a Facebook post. That entire saga adds a certain color to the story because it shows that even in Singapore’s highly managed public sphere, differences do not disappear. They simply take different shapes, and it can happen at a level most people never see.
Lee Kuan Yew died in 2015, and both Hongyi and Shengwu gave eulogies that were made public. I watched both. What struck me was how differently they presented, and how those differences felt like more than personality. They felt like two styles of being Singaporean at the elite level.
Hongyi’s speech was relatively short. He spoke about Ye Ye (grandfather in Mandarin) and remembered a simple message: never give up. There was sobbing that broke the delivery, and the overall impression was of sincerity, loyalty, and a kind of straightforward obedience. It made Hongyi feel like someone who inhabits the system naturally. Not in a sinister way, but in the way a well-trained, morally serious civil servant inhabits a structure: the system is not merely a constraint, it is also a home. He came across like the archetype of the top scholar-administrator: disciplined, earnest, engineered for continuity.
Shengwu’s speech was longer, smoother, and more rhetorically elaborate. That did not surprise me given his background in debate and the humanities. He was emotional too, but the emotion did not interrupt the flow. If I recall correctly, he also hinted, gently, at occasional disagreement with Ye Ye, while still emphasizing a fundamentally harmonious relationship and acknowledging deep respect for what Ye Ye achieved for Singapore. Compared to Hongyi, who felt like a meticulous architect building within the blueprint, Shengwu felt like a more adventurous intelligence: someone who wants the freedom to question the blueprint, test its limits, and sometimes maneuver around it. Yet he still identifies strongly with the system, which is important. It is one thing to criticize a structure as an outsider. It is another to criticize it as family, as inheritor, as someone whose identity is braided into the structure even when he resists it.
This contrast matters to me because it maps onto a pattern I have seen in Singapore. Singapore contains countless types of people, but these two styles represent, in my mind, two apex types. They are the kinds of people who, when they exist in sufficient numbers and occupy the right positions, quietly determine where the country bends over the next thirty years.
The prerequisites are brutal. You have to be unusually smart. You usually need serious resources, whether inherited or self-built, but in Singapore the inherited form is especially visible: the dinner-table exposure, the access to powerful conversations, the early calibration of what “the world” actually looks like. Both grandsons mentioned being able to discuss global affairs with Ye Ye as children. That kind of early exposure is not just information. It shapes instinct. It teaches you what matters, what is possible, what is dangerous, and what is merely noise. Add to that macro and micro situational awareness, ambition, and a certain courage to do things that are larger than a personal career. In a country of about 3.6 million citizens, the number of people who meet those criteria is tiny. That is why, at the top, individual choices can actually tilt national outcomes. Singapore is small enough that one life, if it sits at the right junction, can become history.
My daily observations make this feel less theoretical. I know government scholars who studied at top institutions around the world, then returned to serve the state under bond. These scholars are often fast-tracked. Many ministers and senior leaders in Singapore’s government have scholarship backgrounds. Whatever one thinks of the system, it is hard to deny that these people have real influence over the direction of the country. They are not merely “employees.” They are the state’s long-term strategic investment in leadership.
Then there is the other path: people who intentionally do not take the scholarship route because they want freer career optionality. Some of them end up in positions in the private sector that are equally influential, sometimes more so, because private power is often less visibly constrained than public office. An example is Shou Zi Chew, the CEO of TikTok, who became globally recognizable after U.S. congressional hearings, including the moment where he said, “Senator, I am Singaporean.” I have my own questions about some strategic choices he made, but regardless, people like him shape how the world perceives Singapore and how Singapore navigates power between larger forces.
Chew’s case illustrates a unique advantage that Singaporeans can have. Singapore survives by positioning itself between major powers without fully collapsing into any one camp. It cannot afford the luxury of permanent moral theatre, but it also cannot afford the cynicism of having no principles at all. In fact, Singapore’s demographic reality gives it leverage here. A Chinese-majority population can be culturally legible to China in a way that many other societies cannot replicate, while Singapore’s institutional English, legal-administrative DNA, and global educational pathways make it legible to the West. This does not mean Singapore is “half China and half the West.” It means Singapore has the ability, in the best cases, to translate across worlds.
In that sense, Singapore’s internal diversity is essential to its external strategy. We have Muslim Singaporeans who feel deeply about Palestinian suffering, and we also have citizens who align more instinctively with Israel’s security logic and its civilizational story. On an official level, ministers visit mosques and the country celebrates holidays such as Ramadan, and at the same time Singapore has had meaningful defense and economic ties with Israel. Even the SAR-21 rifle that many Singaporean males used during National Service was developed with Israeli involvement. These are not superficial contradictions. They are expressions of Singapore’s core reality that it is a country that must hold multiple truths without tearing itself apart. If that balance is lost, Singapore becomes fragile, and in geopolitics fragility is an invitation.
From there, I arrive at a picture of what an “elite Singaporean” could look like in the fullest sense, not merely as a high-achiever but as a geopolitical instrument. This person would be deeply literate in world politics, able to understand big forces down to their granular mechanisms. They would also be socially and psychologically agile, able to conceal, soften, or reframe their true stance when circumstances demand it, not out of cowardice but out of strategic discipline. They would ideally hold power that is not fully trapped by domestic political restraint, which is why private-sector influence often matters more than official titles. They would have global reach, operate across spheres, and still possess the sharpness and courage to act, including taking risks when most people retreat into safety.
And here is the irony. I am not convinced Singapore’s local education system and its comfort-oriented, risk-averse environment naturally cultivate this kind of person from the ground up. Singapore produces excellence, but it often produces excellence that is optimized for stability, for predictability, for being rewarded by the system. The apex version I am describing requires a comfort with uncertainty, with friction, with losing face, with making bets that might fail. It requires a kind of worldly hardness that comfortable environments do not reliably produce.
So, in that sense, the best possible version of a Singaporean might have to be shaped partly outside Singapore. Not because Singapore is insufficient, but because Singapore is so well-designed to reduce chaos. Yet the people who move history often have to learn how to walk inside chaos without becoming chaotic themselves. The small-state genius is not just to build a safe island. It is to produce individuals who can leave the island, enter the storm, and still return with something useful.
RJWANG19 
Leave a comment