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.”)

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.”