Lee Kuan Yew was a 73-year-old senior minister when 30-year-old Harpreet Singh Nehal publicly challenged him. The backdrop, to that 1996 televised forum on the Singapore Dream, was that political leaders had become increasingly concerned about the perceived lack of grit amongst the “post-independence generation”: those, like Harpreet, born after 1965. “You have benefited from the fortitude and vision of the founding generation,” lectured Goh Chok Tong, prime minister, in his 1996 National Day Rally speech. “Unlike us, you have not experienced the trials and tribulations of pre-independence and early nationhood…Many of you are absorbed by personal aspirations—promotions, houses, holidays.”

This was rather rich, coming from the ruling People’s Action Party (PAP), which had itself long fostered money-mindedness, consumerism, and individual responsibility (over communal). It had been two years since the party decided to raise ministers’ salaries to astronomical levels; and just months since Lee Kuan Yew (henceforth LKY) and Lee Hsien Loong, his son and then deputy prime minister, had become embroiled in a scandal over unsolicited discounts of over S$1m that they had received in four property purchases. (“Let’s grow up!” LKY had scolded Parliament in the post-mortem. “I am me…it’s not a level playing field.”)

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LKY was at the forum partly to soothe that season’s great affective divide: between, on the one side, an elite political class that could, with or without discounts, afford to buy multiple properties in a red-hot market; and on the other, young Singaporeans fretting about whether they could even get on the first rung of the property ladder. LKY dismissed the concerns of the first participant, a 19-year-old English literature major, by telling her that she should enter law to make money. “We have a lawyer in our midst,” the moderator smartly pivoted, looking at Harpreet. “Do you have any reactions to what the senior minister just said?”

After a brief exchange with LKY about lawyers’ salaries, Harpreet, in a blue shirt, red-and-white tie, and with a thick bob of centre-parted black hair, calmly asked, “Senior minister, if I could. There’s a genuine concern among many Singaporeans that, leaving aside condo prices, even HDB prices have gone sky high. And property prices over the last five years since, they’ve escalated sharply…I wonder, senior minister, if your view is that the government should have taken any steps earlier to check on speculation and if not then, what special facts, senior minister, existed in 1996 to justify these measures now but not any earlier.”

By supporting the housing concerns of the student and others in the audience, Harpreet, with a lawyer’s trademark deference and bullet-proofing, rattled LKY. Singapore’s “founding father” shifted uncomfortably in his chair, and eventually responded with a mix of questionable economics and avuncular tut-tutting. Last year, the clip of Harpreet and LKY’s exchange went viral on social media, with many noting the recurrence today of the same aspirations and concerns.

Soon after that stunning debut, Harpreet was profiled by The Straits Times (ST) in a piece titled, “Epitome of Singapore Dream is a watchman’s son going to Harvard”. ST, perhaps inevitably, asked about political ambition. “Politics is not something you go and do unless you sense within you a deep mission…as of now, I have not been gripped with a burning desire to serve in politics.” Even if the issues haven’t changed, almost 30 years later, Harpreet’s chosen form of engagement has. He appears certain to stand for the opposition Workers’ Party (WP) in Singapore’s next general election (GE), due by November 2025. Now a senior counsel (SC), he’d be arguably the most credentialed opposition candidate in decades, precisely the kind the PAP has been struggling of late to attract.

Harpreet carries with him an immense burden of expectation. His fans expect him to sashay into Parliament and become a dialectical bulwark to the senior counsels across the aisle, notably K Shanmugam, the powerful minister of law and home affairs. Yet if one considers the trajectories of other articulate, South Asian WP lawyer turned politicians who preceded him—such as JB Jeyaretnam and Pritam Singh—there’s every chance that Harpreet has picked up a poisoned chalice.

The temptation is to downplay his charm, because it’s frighteningly easy to get sucked into Harpreet’s orbit. He opened the door with one of his trademark polo t-shirts hugging his lean torso, his white hair blown back with a touch of measured indifference, and his boyish, tanned face shaved so razor clean that one wonders if he’s acting for Gillette versus goatees. He introduced himself, his right hand and penetrating eyes in sync with that characteristic, “I’m Harpreet.” He has a deep voice and a tone that’s direct but not harsh, given to honorifics like minister and macha (Tamil for brother-in-law, but used colloquially for any male buddy). Harpreet, living alone, helped put down bags and take drink requests. He tracked us across the wood-panelled floor, after we, the guests, disarmed by his aura of emotional and intellectual warmth, had initiated a house tour.

But where should we begin? The glorious, sea-facing balcony where potted plants dance to the winds blowing in from the direction of Batam, visible across the Singapore strait? Or the sparkling yet spartan kitchen—read: bare fridge—around which fake plants dangle listlessly? Should we dawdle over the gleaming, gold saxophone in the corner, an essential part of the assemblage of the Singaporean renaissance man? Or wait for Harpreet to stream his meditative morning Spotify playlist, later losing himself in Ennio Morricone’s soundtrack for “Cinema Paradiso”? 

There are books everywhere. Like in other homes of the well-read, one can’t help but wonder if the placement of each reflects function or optics. On the coffee table and sideboard are Barack Obama and Martin Luther King Jr., so crucial in his current political awakening. “Once I get sick of non-fiction and my spirit feels it needs some reviving I gotta find the appropriate piece of fiction.” Two have made a “huge, huge impression.” Silence by Shūsaku Endō is about a Jesuit missionary who is persecuted when he travels to 17th century Japan. Its deeper themes are around a silent God who accompanies followers through suffering. “Like any really good book does, you don’t realise that at the time, but by the time you’re finished, you’re a different person.” Mornings in Jenin by Susan Abulhawa, meanwhile, had him “bawling” throughout. “It traces the life of three generations of Palestinian women from pre-Nakba, pre-1948, to the modern day, and it weaves in UN reports so that at various points in time, it is difficult to tell what is fiction and what’s non-fiction, and the two are so beautifully merged.”

Perhaps there is a deeper cosmic resonance. It is to that same prewar period, to another territory on the verge of being torn asunder by British misadventure, that Harpreet traces his ancestry.

In the 1950s he returned to a partition-lacerated Punjab, where relatives had identified for him a possible bride in her early 20s, about a decade younger. Unlike his dad, Harpreet’s mum had received some basic education, in a village school up till the equivalent of early secondary. So while her husband earned a living as a jaga, she ran the house, and was “extremely strict”, Harpreet said. He believes he benefited from a father who was “extremely loving and encouraging and welcoming in every sense”, who offered “a very high degree of emotional support and security”, balanced by “a mom who was very clear about discipline”, albeit with great empathy, especially for the poor and the underdog. 

Harpreet, the youngest of three, was born in 1966, in a Teochew kampung in Upper Serangoon. It was home to only two non-Chinese families, theirs and a nearby Tamil one. His parents would speak to the kids in Punjabi, and his sister, even though she knew it, would respond in Teochew. “It was a language that you were just immersed in and it was wired into your brain by the time you were a kid.” Just beyond were the government quarters for (mostly Malay and Indian) daily-rated workers. “The poorest of the poor,” Harpreet said. “Even in our kampung, we did not have toilets in our house, we had these outhouses, jambans. So you would have these chaps who would come and clear the outhouses.” Through them the Malay language also flowed into the Teochew kampung. Later government resettlement deposited Harpreet’s family into a three-room flat nearby on Hougang Avenue 3. Put another way, Harpreet’s entire upbringing was in an area famed for its “Hougang Spirit”, which the WP would win for the first time in 1991.

Harpreet enrolled at a PAP kindergarten—speaking Teochew to teachers—before going to Parry Avenue Boys’ School and then St. Andrew’s Secondary School. Next was Hwa Chong Junior College, where he also got his private pilot’s licence. His life ambition then was to become a fighter pilot, but myopia and astigmatism later scuppered those plans. He got accepted to do computer science at the National University of Singapore (NUS) in 1987, but one fateful week in Malaysia, near the end of National Service and just months before the start of NUS’s term, changed the course of Harpreet’s life. He spent it with a relative who ran his own law firm in KL, whose real-world advice was coincidentally complemented by fiction—Harpreet watched two movies involving lawyers fighting for truth and justice. “It’s a mystery that I cannot rationally explain. At the end of that week, I knew in my bones that I had to do law.” Harpreet matriculated as a computer science student but NUS later processed his “last-minute transfer” to the law faculty.

Quick-fire career progressions followed: finishing near the top of his class; joining Drew & Napier in 1991; completing his Masters of Law at Harvard, funded by an interest-free loan from his firm; being invited to teach the summer negotiation programmes at Harvard in 1994-95, right before that famous encounter with LKY; and leaving Drew & Napier in 2011 after 20 years, having made equity partner, for Clifford Chance, one of the world’s biggest law firms. He describes several mentors and inspirations during that period, most of all Davinder Singh, his pupil master at Drew, and also a former PAP member of Parliament (MP) known for representing the Lees. “I have tremendous respect for his intellect; his formidable work ethic; his doggedness in going after every single point.” Harpreet said there is also a side to Davinder Singh that few see. “His care for the man in the street. For the poor. For the underprivileged.”

In mid 2019, Harpreet left Clifford Chance and founded Audent Chambers, a “boutique law firm specialising in high end, complex litigation and arbitration”. Harpreet said he chose the name because he believes its Latin root, audentia, captured this move from large firm to niche practice: audacious, bold, courageous.

Over this same period what was perhaps more time consuming, and undoubtedly more rewarding, was family life. On the wall in front of Harpreet’s home office desk—Audent is a remote-first organisation—are numerous photographs featuring his four children: Niam, 28, Sach, 27, Nitasha, 22, and Aman, 21. (Their mum and Harpreet are divorced.) Unlike the finer details of Harpreet’s professional career, which I heard for the first time only during these interviews, he’s told me many stories of his children over the years. Niam, the lawyer who also wants to sail the world; Sach, the data scientist who’s been to Burning Man twice with Niam and Harpreet; Nitasha, the zoologist who’s “extremely bold and adventurous” and likes diving with sharks; and Aman, the “baby” of the family, the only one still in college. “So he’s the one we call the Immaculate Conception. Like, how the hell did that happen?” he said near the end of that 12-minute Jom house tour, seven of which were spent in front of the children’s wall.

They’re currently pursuing their respective careers in the UK, and Harpreet tries to visit them every quarter. Our last interview took place just before he was due to surprise Aman in London on his 21st birthday—a scheme plotted with Aman’s siblings, which seemed to invigorate the strategist in Harpreet more than any case. Before each of these trips, there’s a great anticipation that imbues his spirit, as if he’s readying himself to simultaneously expend paternal instincts, indulge vicariously in a youth more privileged than his, and act as the spiritual bridge between an orphaned Sikh boy born in a remote corner of the Indian sub-continent—and four Singaporeans with far more choices and certainty in life. “[I]t occurred to me that the most valuable gift I can give him [Aman], far more precious than any material thing, is a collection of life lessons from father to son,” said Harpreet on Facebook last month. “So, I went out and bought a special journal and spent several hours over the weekend reflecting and writing these thoughts to him, gleaned from my own life experience.”

But surely his zipping between Singapore and London will be affected if he enters Parliament? He doesn’t think so, since at most there are “three or four days of sitting in one month…the question is how do you balance that with your commitments on the ground?” In that, he’s entering the political fray at a convenient time, with Singapore’s culture of manic overwork increasingly under scrutiny. Civil servants and politicians can no longer impress people by valorising their supposed lack of downtime. Work-life balance, mental health, and human connections are the buzzwords of the post “first-world” enlightenment. Rather than Harpreet’s kids retreating from his life, what could happen, as is common in the US but much less so in Singapore, is a relatively more public profile for them, whether accompanying him for WP dinners in Hougang, as some already have, or baby photos popping up on his social media feed. (Was that part of Aman’s 21st surprise?) 

The doting father-family man narrative also involves his mother. Last November, one of the more notable reveals about Harpreet’s WP affiliation was a social media post in which he’s wearing the party polo t-shirt while hugging his mum, resplendent in purple. She was thrilled to see him in party colours, he later told me. “She said, ‘You know, Pritam [Singh] is fighting this thing alone. You go and help him.’ It’s a very Sikh way of looking at it. Somebody else is doing battle. Somebody is doing right. Don't leave them alone.” A separate post showed Dennis Tan, her WP MP in Hougang, visiting her this May. “Dadiji”, grandma, she replied, when Tan asked what he should call her. 

Without them and his life partner, Harpreet might never have joined a political party. They were with him in 2017 through what he described as the darkest season in his life, when he faced an allegation that risked “tearing down everything I had worked for”. Following observations by the High Court on witness preparation in the case of “Compañia De Navegación Palomar, SA v Ernest Ferdinand Perez De La Sala”, the Law Society of Singapore initiated a disciplinary proceeding against Harpreet. “The allegation was made that I had acted unethically, together with my colleagues.” 

Harpreet had by then been in the profession for almost three decades, and SC for a decade. He believes it was “probably one of the first few times where an allegation of this seriousness” had been levelled against an SC. Lawyers in Malaysia, Singapore, and the UK, he said, were discussing the case: “a huge public humiliation.” When he first heard it, he cooped himself up in his apartment for three full days. “Because where do you hide your face?” If found guilty, he could have been disbarred. The process took an entire year. “We were completely vindicated and [the tribunal] found really [that] the allegations had no merit.”

Two conversations remain within him. “The cave you fear to enter, holds the treasure you seek,” his brother had told him, quoting Joseph Campbell, an American writer. “Basically, just saying, this thing you're so afraid of, it’s got the power to transform you. And go and do battle with this demon. And you will find yourself in the course of the year, just transforming.” An unnamed friend, meanwhile, engaged Harpreet in casual life coaching, getting him to clarify priorities. The worst case scenario, said the friend: “you get disbarred, you’ll have all the money in the world, all the time in the world to spend it, you’ve got your health, your kids love you.” The real source of Harpreet’s grief, his friend identified, was his “need for public approval”, his “standing in public”. From that moment, Harpreet said, he became “more ready to at least be less concerned about what the world thinks of me.” That was his base fear all along, he realised, when it came to opposition politics. Not a knock on the door at night, or a bullet in the head, but his public image. Face.

The one-year journey broadened his political imagination, opening his mind to new possibilities. “He’s grown so much from that [disciplinary tribunal] experience that I think he’s ready to take on this [political] challenge,” Nitasha told me. She shared the advice Harpreet gives his children when they’re fearful: “You need to make sure that you’re doing the right thing. And if you believe in it, speak up for it no matter what other people might think or what the consequences might be.” Harpreet’s political evolution is all the more gripping because of his flirtation with the PAP ahead of the 2006 GE. A full cycle before Lawrence Wong, prime minister, entered politics, Harpreet was also keen to wear white, to sit on the same side of the chamber as Lee, Shanmugam, and all the other household names he may soon be up against.

He attended a few tea sessions, including one with the younger Lee. The subsequent, “more intense rounds”, included one-on-ones with Shanmugaratnam and S Jayakumar, then deputy prime minister. The final round was with the whole cabinet, including the senior Lee. Harpreet forgets exactly what was discussed, but maintains that his political views haven’t changed since then: “Singapore will be better with more political liberalisation, a more open media, a more open education system…I think we had a frank conversation about why I homeschooled my [two elder] kids, for example.”

Harpreet stepped out. The cabinet deliberated. When he walked back in, they told him something to the effect of, “There are different ways to contribute to this country. We just don’t feel that running as a candidate for the PAP would be the route for you.” He knows of no further explanation for why he didn’t make the cut. I asked if he was disappointed. “There is the allure of being in your 30s, a member of parliament with an established system. Of course, there would have been some measure of disappointment. But with the benefit of hindsight, I would say I’d be a different person.” (He also applied to be a nominated MP in 2007, after he became SC, but wasn’t selected.)

Harpreet’s disillusionment with the PAP grew in the 2010s, as it did for many: the PAP’s vote share dwindled from 75.3 percent in the 2001 GE, the last before Lee took office, to 61.2 percent in 2020. “The fork in the road for the PAP was when they decided that Tharman would not succeed PM Lee. I think they made a conscious decision to take a different road.” From that moment, the system grew “more hostile” to independent, critical thinking, Harpreet said. He identifies signs of creeping authoritarianism over the past decade under Lee: the parlous state of the mainstream media; the closure of Yale-NUS college; the passing of “very broad laws” like POFMA; the decision by “some of our best” independent thinkers, such as (academics) Cherian George, Donald Low, and Kenneth Paul Tan, to stay outside Singapore; and the problematic circumstances under which Halimah Yacob assumed the presidency in 2017. 

Harpreet, having been groomed by Davinder Singh, former PAP MP, having worked alongside many establishment stalwarts, having been shortlisted by the PAP, has about as much of an insider’s view as anybody in the opposition. For a time he was the scholarly contrarian of choice in the ST’s opinion pages—including one piece on POFMA and another on the Foreign Interference (Countermeasures) Bill (Fica). Many people pine for change from within the system, he said, because “it involves no cost to any of us. All of us want the system to just evolve with people on the inside. [But] I just don’t see that system evolving…I just don’t see this thing self-correcting. It's moved so far down in a rightward direction that anyone hoping for change to come from within the PAP is going to be disappointed.”

Singapore defies comparison because of its geopolitical exceptionalism. As the world’s only global city cum sovereign state, the tensions we face are unique. In some ways it makes governance easy. Compared to every other democracy, Singapore as a polity is relatively compact and homogenous—no rural-urban tensions to manage, for instance. (Fear mongering about the few ethno-religious tensions obscures the fact that most Singaporeans are urban, middle-class, and with a multicultural outlook.) In other ways, governance is harder. National defence, for instance, necessitates gargantuan sacrifices of land and labour in a small city, as well as the cultivation of a national identity that is occasionally suspicious of foreigners, if not outright nativist—antithetical to the openness a global city needs.

Still, analysts do occasionally look to other Asian countries for clues about our likely evolution. South Korea and Taiwan, for instance, are both East Asian, export-led tiger economies that transitioned from autocratic rule to feisty multi-party democracy. Malaysia, with its shared history and similar culture, inevitably invites comparisons. In the past decade, as strongmen rulers have gained power around the world, some Singaporeans have started to look at another illiberal democracy whose inner workings might reflect our own: Putin’s Russia. When one considers electoral dynamics, the hobbled mainstream media, or the way the regime deals with critics, Putin’s Russia—or, more precisely, what it was prior to invading Ukraine—can seem like a more savage version of Singapore. Same same but different violence. It’s unsurprising that shortly before he died in 2015, Lee Kuan Yew called Putin “one of the best leaders worldwide.”

The parallels are especially startling when one considers the psychology and social conditioning of those in the system. In “History will judge the complicit”, Anne Applebaum seeks to explain why Republicans might have “abandoned their principles in support of an immoral and dangerous president [Trump]”. Applebaum, a staff writer at The Atlantic and analyst of former Eastern bloc countries and modern autocracies, notes similar patterns of behaviour amongst apparatchiks in places like East Germany, the Soviet Union, and Putin’s Russia. She identifies several virulent beliefs of collaborators, including “We can protect the country from the president”; “I, personally, will benefit”; “I must remain close to power”; “My side might be flawed, but the political opposition is much worse”; and “I am afraid to speak out”.

Some Singaporean political observers zeroed in on this passage: “In his recent book on Putinism, Between Two Fires, Joshua Yaffa describes the Russian version of this syndrome. The Russian language, he notes, has a word—prisposoblenets—that means ‘a person skilled in the act of compromise and adaptation, who intuitively understands what is expected of him and adjusts his beliefs and conduct accordingly.’ In Putin’s Russia, anyone who wants to stay in the game—to remain close to power, to retain influence, to inspire respect—knows the necessity of making constant small changes to one’s language and behaviour, of being careful about what one says and to whom one says it, of understanding what criticism is acceptable and what constitutes a violation of the unwritten rules. Those who violate these rules will not, for the most part, suffer prison—Putin’s Russia is not Stalin’s Russia—but they will experience a painful ejection from the inner circle.”

Any attempt to blindly equate Putin’s underlings with Singaporean establishment folk is bound to collapse in absurdity, such are the differences. Still, interactions with officialdom here, and the countless testimonies from disenchanted academics and former civil servants, certainly suggest the existence of platoons of PAP prisposoblenets throughout the country. “[The article] has helped me understand the possible motives of some who continue to flirt with and enable the status quo,” Harpreet told me in early 2021. That same year, he became even more involved in efforts to address socio-economic issues, notably giving a “sizeable donation” to the Saw Swee Hock School of Public Health at NUS, for its research project on long-term healthcare options for an ageing population. Also that year, he started volunteering with Leon Perera, former WP MP, at his meet-the-people sessions.

For while the PAP kept disappointing him, the WP impressed. Influences include Low Thia Khiang, who first won election in 1991 and famously handed over the leadership reins to Pritam Singh (even as the PAP rejected Tharman as leader, alluding to his race). “Over time, he [Low] has significantly improved the brand of the party, including the people he brought around.” The entry of lawyer Chen Show Mao into politics in 2011 also had an impact on Harpreet, as did the relentless “plugging away” by Sylvia Lim, whom he’s known for many years. Pritam Singh’s ability to stay “true to the course”, and remain “calm and collected” in the face of lawsuits over a long period were important. “You form a sense of the people, their characters, you know how they deal with crises.” It’s a similar feeling about Jamus Lim: “cool, calm, unfazed.” From Low Thia Khiang to Jamus Lim one can also perceive the WP’s shift in its supporters’ socio-economic milieu: from its Hokkien-Teochew “heartland” to a more privileged, progressive segment of Singaporeans. It’s a divide that Harpreet, from Teochew kampung and Hougang HDB to the peak of the legal profession, can presumably help bridge. 

Perera, who often goes on long walks with him at the beach, is perhaps the person most attuned to this politician-in-the-making. Harpreet is so much more than just his profile and calibre, he told me, describing him as a “conviction politician”, somebody who has the motivation to make things better for the next generation, who is prepared to devote energy and time, and to take certain risks in life, to give back to the country in that way. “Singaporeans to some degree have been starved of conviction politicians. We have TikTok politicians.” Perera believes there are parallels between the renaissance man Harpreet and, oddly, one of the toughest hatchet men ever. “People didn’t always agree with LKY and everything, especially some of his zany ideas, polygamy and graduate mothers. I mean, people rejected those ideas, but they respected him because they knew that he was coming from a place of conviction. So Harpreet definitely has that. And that gives him iron and fire in his belly.”

His WP walkabouts, where he’s felt the warmth of Singaporeans—unafraid to engage, and encouraging of the opposition—are also starting to shape his view. Over 50 years since independence, he’s been surprised by “the number of [mostly Chinese] households where English is not spoken as a working language…they're not plugged into the best opportunities.” He has ideas for more concerted neighbourhood reading programmes, possibly resourced by a “local Peace Corps kind of thing” involving parents more privileged with time. A “much more broad-based education system” is what he’s always championed and embodied, from the time he and his ex-partner home-schooled their older two kids in the early 2000s. He cites two long-standing WP suggestions: smaller class sizes, and a through train from primary one to secondary four, which would do away with the much-maligned Primary School Leaving Examination.

Harpreet’s pro-bono work, meanwhile, points to an indefatigable drive to defend underdogs: a Malay man he’d grown up with in Hougang, seemingly unfairly accused of hurting somebody in a void deck tiff (“turned out to be a landmark decision on Constitutional law,” Harpreet wrote); an Indonesian helper possibly facing the death penalty for murdering her employer, who ultimately was sentenced to life imprisonment (and whom Harpreet still visits every year); and a number of cases related to gay rights, the last of which, in 2022, almost certainly propelled Parliament to repeal S377A, the law that criminalises sex between men, later that year. Their legal team included, perhaps surprisingly for many Singaporeans, a few religious people, including Audent’s Jordan Tan and Harpreet. “A Christian Advocate’s Role in the Constitutional Challenge against Section 377A”, Tan wrote in 2019. 

Harpreet was “born and raised in a conservative Sikh family”, and said that, “in my spiritual journey over the years, I have been enriched by my exposure to various spiritual traditions.” In his home office, across from his children, is an oil painting of Jesus Christ being brought before Pontius Pilate, with the Roman governor’s face knotted in conflict in the foreground. “Pilate is pulled in different directions. He knows the man is innocent, but doesn’t want to pay the political price for letting him go,” Harpreet said. “I’ve found my appreciation for my Sikh faith deepened by these multiple spiritual influences, each strain deepened by the others.”

Liberals, perhaps buoyed by Harpreet’s S377A work, may be disappointed if they think he’ll be their standard-bearer. For instance, while he doesn’t agree with a mandatory death penalty, he’s not in favour of abolishing it altogether, as many (including Jom) are. He’s not ready to accept that there is no circumstance whatsoever that might warrant it. “For example, somebody deliberately plants a bomb that kills a very large number of people, including women and children and the elderly…rather than making it mandatory, leaving no discretion at all to our judges, I would say, leave it to our judges.” Harpreet, who believes Singapore has one of the best judiciaries in the world, had two other criminal justice suggestions: videotaping all interrogations of accused persons so as to avoid arguments about whether statements are voluntary; and removing the glass separation between prisoners and visiting family members. “I’m not sure that the right thing to do is to deprive people of human contact with their loved ones.”

On the issue of the freedom of assembly and speech, Harpreet similarly adopts a position perhaps too conservative for some on the left. “We need to stop talking about these things behind closed doors,” he said, of contentious issues such as race and religion. “You stifle discussions within the broader society, and you limit society’s ability to deal with these differences and assimilate them.” Though broadly in favour of more openness—subject to the usual restrictions on hate speech and incitement to violence—Harpreet does, however, express caution over the Israel-Palestine issue. “You allow for it, but how do you then police what is said at these events?…that is where I have significant difficulty with the whole Gaza issue, because of its propensity to just spiral out of control.”

Perhaps Harpreet is, indeed, tailor-made for the WP, sometimes referred to as PAP-lite. Its approach to electoral politics and its actual policy proposals have always been more incremental than radical, in keeping, arguably, with what most Singaporeans want. Harpreet may think the system has stopped evolving, but many PAP fans believe it’s adapting at just the right rate, thank you very much, particularly under new leader Wong. The outcomes of the PAP versus WP contests at the next GE may partly reveal what kind of evolution voters today want.

Harpreet is, for sure, constantly grasping for his own truth on issues, repeatedly prodding Jean and me on areas in which he feels he can learn something, whether Sinophone households and language policy or political dynamics. “My starting point is, I have my biases. On any one issue, I may be too pro or anti or whatever. I may feel too strongly about a particular issue. Or I may just have a natural blind spot.” One of the many surprising tomes on his coffee table is Never Give an Inch by Mike Pompeo, secretary of state under Donald Trump. “I felt I wanted to read that just to get a window into people on the extreme right in terms of how they view the world.”

Harpreet stress tests his beliefs and positions with an inner core of friends and family, among whom there are some “extreme liberals and extreme conservatives”. On occasion, the conservatives might feel he’s “overcorrected” and then prod him to “take a more aggressive stance” in his writings. “The ultimate position I take is one that I feel is consistent with my own conscience. I am not one that seeks to please everybody, because on some of these issues, you cannot please everyone. You cannot be all things to all men.”

Does Harpreet have the stomach for a fight? “He’s not naturally given to fights, and he’s very conciliatory. He doesn’t like conflict generally,” a lawyer who’s worked with him told me. “But I think that he’s going to steel himself for it and do it because he’s a very principled person…it would be very unpleasant, he wouldn’t like it, but he’d be able to do it.” According to Perera, “the nail that sticks out gets hammered down in Singapore politics.” He claims the PAP has historically hammered these nails that stick out both before the election and, if they win, after. (It’s a metaphorical inversion of the WP’s own symbol, the hammer.) He’s convinced that Harpreet is one such protruding nail, and thus will have to defend himself against “that kind of attention”. 

Harpreet is certainly aware of all this. Part of the reason the interviews were tricky is that Harpreet, having spoken without a filter to me as a friend for years, and having to now size me up as a journalist, had trouble navigating the line between candour and caution. “I will be as frank and open as I can, and more than happy to just be more open rather than guarded. So just shoot, and I’ll share,” he told Jean and me on that first day in February.

A month later, having had time to process how his words might land on a presumed average voter, he’d changed his mind. Some things would be off the record. Though we’d offered Harpreet the right to retract lines, as we do all our profiles, I pushed back. This little editorial tug of war between us persisted till a few weeks ago. One of the unforeseen treats of this profile was an opportunity to observe up close this professional moulting. The shedding of a skin so admired may expose an uncommon rawness. “One day I feel myself one way. One day I feel myself another way,” he said, when I asked him, late one night, how he’s doing.

We spoke about his honest relationship with Pritam Singh, and the risk that external provocateurs might try to present the illusion of infighting to stir up trouble. (Does Harpreet want the top job?) We looked around to see if anybody might be watching him, either for surveillance or fandom, both of which I suspect I’ve seen. Harpreet pulled on and off his reading glasses, as new bottles of Carlsberg and buckets of ice appeared (he drinks a heavily diluted beer). We later crossed the road, and I ate at the famous Hokkien mee stall. A new migrant from Punjab was helming the drink stall. They spoke in Punjabi, and I wondered if Harpreet’s father, some 80 years ago, might have also met a second-generation Punjabi that welcomed him here. It is a unique corner of our little red dot that seems to compress culture and time. Harpreet Singh looked at once so at ease and also a bit of a curiosity. 

I tug at the strands of his life: jaga’s son to Harvard grad; LKY challenger to PAP tea sipper to WP (maybe, someday, possibly) candidate; English to Punjabi to Teochew to Malay to the Queen’s Singlish; and, of course, wannabe fighter pilot to wannabe pilot fighter. And I wonder: what exactly will Harpreet the politician be like? Many questions remain. He believes he’s no longer so bothered about “face”, about what the world thinks of him. But if I think about the way he hosts, and he presents himself and his space, and the way he obsesses over his own progressive parenting and his relationships with his kids, he obviously still cares, like all of us do. What if he faces a reckoning far worse than the disciplinary tribunal?

In terms of political character, is Harpreet really akin to LKY, or is he some avant-garde version of conviction politician, less strong-armed leader than persuasive people person, iron and fire in the belly but not in his words? Which kind of conviction politician do Singaporeans today want? In terms of relatability, can the kampung boy and senior counsel keep effortlessly code-switching across the income divide, connecting with, and attending to the concerns of an increasingly diverse electorate? There is, in that space of contemplation, also the realisation that a person is as much what they make of themselves, as what we make of them.

Electorally, will Harpreet become a permanent pillar of the opposition, assiduously keeping the PAP in check, or might he actually propel the WP to one day win a GE and form the government? Perhaps that is the wrong framing, a false binary, for either outcome would be potentially beneficial for Singapore. Among other possibilities is that he never actually wins an election; and the most worrying for him, that the Leviathan, desperate on its imagined deathbed, somehow lures Harpreet into making a mistake, which is then seized upon to destroy his reputation. It may not even be a single catastrophic incident, but a series of small, niggling perturbations to the force, which render Harpreet less potent in the political realm. 

That we countenance such a scenario reflects the depressing politics of our past. That we hope it may not come to bear speaks to the optimism we have about our future.

Sudhir Vadaketh is Jom’s editor-in-chief. Additional contributions by Jean Hew. Sudhir is also indebted to Tim Chee, Kathy Anne Lim, Loh Peiying, Sivanathan Jheevanesh, and Corrie Tan.

Letters in response to this piece can be sent to sudhir@jom.media. All will be considered for publication on our “Letters to the editor” page.

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