The Greatest Showman
The left has pinned its hopes on Jagmeet Singh, a charismatic leader with a taste for flashy suits and a following that should make Justin Trudeau nervous. The making of a political superstar
It was spring 2017, and Jagmeet Singh needed a catchphrase. He was about to announce his campaign for the leadership of the federal NDP, and his odds of victory seemed long. He was a novice with only six years at Queen’s Park behind him, better known for his fancy wardrobe than his political prowess. So he turned to the 21st century’s darkest art: creative branding. Singh called his friend Mo Dhaliwal, who runs Skyrocket, a digital marketing agency in Vancouver, and tasked him with creating a central identity marker for his campaign—something sticky and stirring that would convince both NDP veterans and new members alike that there was some substance inside those $2,000 bespoke suits. Dhaliwal and his team grilled Singh with questions about his political convictions (social justice, poverty reduction, anti-discrimination), his childhood (the racist slurs he endured growing up in Windsor), even his clothes (which he sees as a sort of social armour).
As Dhaliwal brainstormed with his deputies, he noticed two motifs that kept coming up in Singh’s speechifying: the idea that everyone is spiritually connected, and the imperative of facing adversity without fear. He swirled those concepts together and concocted a catchphrase: “Love and courage.” There was no swelling music, no triumphant eureka moment. Singh liked the phrase, but like any good socialist, he sought consensus, consulting his team, his family, friends, volunteers, basically anyone he’d ever met. The young utopians on his payroll loved the line. It was simple yet expansive, sentimental yet muscular, a rhetorical jewel that seemed plucked from a Tony Robbins life-coaching session. The old-school NDP establishment hated it. They feared that the phrase was too soft, that it highlighted his weaknesses and outsider status. In the end, Singh sided with his team. “It was never meant to be just a slogan. Love and courage is an indication of my ethos,” he told me.
Four months later, Singh was at a rec centre in Brampton, hosting one of his regular events, also known as JagMeet and Greets. He wore a three-piece black suit paired with a marigold-hued turban that matched his campaign posters. As Singh stood in front of the crowd, testing his microphone, a woman in jeans and a messy ponytail approached him. “We know you’re in bed with Sharia!” she barked. “We know you’re in bed with the Muslim Brotherhood! We know by your votes!” Her name was Jennifer Bush, and she had attended anti-Muslim protests. Singh is Sikh, not Muslim, but that didn’t stop Bush. Though he projected an Obamanian chill, inside he was panicking. “My immediate thought was, ‘There’s no way a tape of a Caucasian heckler and a turbaned bearded man is gonna look good,’ ” Singh told me recently. “It makes me look like the Other. It makes me look like there’s something wrong with me.” He ignored Bush and broke into a chant: “What do we believe in? Love and courage! Love and courage!” Soon the audience was cheering along with him, drowning out the heckler. A video of the incident soon went viral, racking up hundreds of thousands of views. Singh’s serene response—and seemingly spontaneous mantra—earned online support from BuzzFeed, CNN’s Jake Tapper and the actor Jessica Chastain. His slogan was inspiring thousands of idealists across the country.
Overnight, Singh became a political megastar. Within a week, he had overtaken his main opponent in the federal NDP race, the veteran Northern Ontario MP Charlie Angus, in the polls. By the time the leadership convention arrived in early October, his triumph seemed inevitable. He signed up some 47,000 of the NDP’s 83,000 new members, and he swept the first ballot, clinching the leadership with 54 per cent of the vote. When his victory was announced at the Westin Harbour Castle, the roar was so explosive that his 67-year-old mother, Harmeet Kaur, kept her ears plugged to muffle the din. As the crowd hollered his name, he thanked them for pronouncing it correctly (it’s Jug-meet as in Jughead, not Jag-meet as in Jaguar). Before the day was out, celebs like Seth Rogen and the director Ava DuVernay had all tweeted their accolades. “A big deal. Congratulations to @theJagmeetSingh on his decisive victory,” DuVernay wrote. “First person of color to lead a major political party in Canada.”
Jagmeet Singh is the most magnetic leader to ever preside over the NDP (sorry, Jack). And if that sounds like a low bar, we’ll raise it: his natural charisma makes even the dashing Justin Trudeau look stiff by comparison. His default mode is jolly and relentlessly energetic, and he seems to inspire adulation in everyone he meets. “He’s a happy warrior. He’s always got a smile on his face, but he’s ready to fight for people. He will never back down from that,” gushes his long-time friend and former campaign manager Amneet Singh.
Jagmeet has a taste for dandy luxuries that don’t comport with the monkish minimalism of his party. He wears bespoke suits in the slim British style—his favourite is a brown tweed with cobalt-blue stripes, designed by a tailor in New Delhi, which he often pairs with a millennial-pink turban. He owns two Rolex watches, an Oyster Perpetual Datejust and a Submariner (both were gifts); a crimson BMW coupe; and six designer bicycles. “I have just an absurd number of bikes,” he says. “More than one person should have.” His kirpan, the ceremonial Sikh dagger he wears under his jacket, is a steel design by a metalworker outside Boston. Since joining Queen’s Park in 2011, Singh has become one of the city’s most devoted partygoers, a regular at King West nightspots and gala fundraisers, at fashion shows and Raptors games.
He is not a punctilious technocrat like Tom Mulcair, nor a folksy policy wonk like Jack Layton. In his first five months as leader, he’s spoken mainly in generalities that hew to the party line, trumpeting pay equity, climate change awareness and Indigenous reconciliation. He relies on populist platitudes that appeal to the working class, racialized people and millennial voters who feel screwed over by boomers. And although he’s sincere, steadfast and radically empathetic, he rarely digs into the details of issues he discusses. The thing is, he doesn’t have to—at least not yet. The NDP doesn’t need a minutia guy. It needs a big-picture guy. Singh’s brief isn’t to reinvent the party. He has to keep it alive, to use his force of personality and media dexterity to recruit new members and get his MPs elected. In an era when the prime minister is photo-bombing weddings and launching an international craze for novelty socks, his competitors need to match his celebrity. They need to fuse spectacle with politics, to infiltrate pop culture, to sublimate their message into a flashy brand. They need to make themselves unforgettable.
Singh has mastered that art. Aside from his suits, his sartorial signature is his collection of Pantone-hued turbans. He’s been wearing a turban since he was a teenager, but he only started buying brightly coloured pieces after he entered politics. He owns at least 20 now, most of which he gets at shops in Mississauga and Brampton. “You see lots of people wearing a turban, but not many of them rock a pink one,” he brags. For Singh, they are as much a political statement as a stylistic choice: he believes that a turban in a playful, vibrant shade upends the racist association with menace and otherness, that it disarms people and causes them to re-examine their prejudices. And he’s right. It works. But there’s a fringe benefit, too. When he’s the only guy in the room wearing a turban as bright as a Crayola marker, everyone is looking at him.
The leader of Canada’s New Democratic Party currently lives with his parents and younger brother, Gurratan, in a home that Jagmeet bought in Meadowvale, a looping Mississauga subdivision. He’ll finally be out on his own later this spring, when he moves into his new house near Trinity Bellwoods Park, which his father bought in 2016 for $800,000. Jagmeet found the place and oversaw the renovations. “Everything we do is a joint thing,” Singh says.
Singh is a brawny five foot 10, and his turban adds at least three inches to his height. Gathered inside is a tumbling mass of wavy black hair that, let loose, tumbles halfway down his back like a shampoo commercial. He’s been growing it since he was eight years old, in accordance with the Sikh faith, which prohibits adherents from cutting their hair. The same goes for his chest-length beard, which is wiry and puffy and spangled with just enough white to make it look as if he recently ate a powdered doughnut. His features are aristocratic and solemn, his brow naturally furrowed, but in conversation his face relaxes into an elastic warmth. He’s as excitable as a teenager, gesticulating madly and leaning in close enough that you can smell the banana he had for breakfast. He flits between subjects at a quicksilver speed and, at 39, speaks fluent millennialese. He’s the kind of guy who says, “Totally, totally, hundred per cent!!!” when he’s excited about something. If Jagmeet Singh were a Harry Potter character, he’d be a Hufflepuff.
He’s also an indefatigable extrovert. He’s a guy who loves meeting people, who doesn’t mind the calloused palms from perpetual hand-shaking, who throws hip-hop deuces in his Instagram photos, whether he’s posing with a gaggle of star-struck 20-something NDP volunteers or the rapper Post Malone backstage at the ACC (Singh listened to Malone’s track “Congratulations” to pump himself up every day on the campaign trail). He doesn’t touch alcohol—he’s seen the effects of alcoholism in some of his family members—but he loves going out on the town. When he and Gurratan used to visit Toronto from their hometown of Windsor, Singh would go into full explorer mode. “He was like, ‘We’re in Toronto! We’ve gotta walk around and see it all!’ ” recalls Gurratan. “True to his nerdy self, he’d buy up every Toronto guidebook. That’s how he’d find restaurants.” Jagmeet still possesses a tourist’s enthusiasm for the city. A few years ago, Mo Dhaliwal—the guy who came up with “Love and courage”—visited Toronto. “He took me on what I can only describe as a date,” Dhaliwal told me. They met at Queen’s Park, where Singh waited with his bike and a spare for Dhaliwal. They spent the next five hours cycling around town, stopping for snacks at restaurants in various trendy neighbourhoods.
You don’t often see federal politicians out partying, but Singh regularly shows up at Byblos (he’s a fan of Charles Khabouth), the Playa Cabana taquerias (the owner, Dave Sidhu, is a friend), and the Chase (he’s vegetarian, but he loves the schmoozy patio and the view). He’s usually accompanied by his posse of best friends—among them the visual artist Babbulicious, the YouTube star Jus Reign, the photographer Harman Dulay and the rapper Fateh Doe. They pose in formation like the Reservoir Dogs, a rainbow of pastel turbans and pocket squares.
The latest addition to Singh’s social circle is his partner, Gurkiran Kaur, a 27-year-old entrepreneur whose clothing company puts modern twists on Punjabi saris and salwars. They met in 2010, when Singh gave a seminar at York University, where Kaur was studying business. She immediately developed a crush on him. “It was superficial at first. He’s really charming, and his eyes are so pretty,” she gushes. They became friends and went on their first date in 2011. Singh remembers how, over dinner, Kaur told him he had dirty fingernails. “I’m normally a very confident person, but it made me self-conscious,” he says. He excused himself and washed his hands. When he returned, she asked him if he’d cleaned his nails. “I loved that gutsy boldness. She called me out and kept me in check,” Singh says.
They saw each other on and off for the next few years until February 2017, when they made their relationship official. They kept their commitment secret for almost a year to protect their privacy while the public thirstily speculated about his relationship status. “It was the funniest thing. If you did a Google search, the first things to come up were ‘Jagmeet Singh single, Jagmeet Singh married, Jagmeet Singh wife,’ ” he says, clearly chuffed at the attention. Despite their furtiveness, Kaur quietly watched her partner at every public event: she looked on in horror while Jennifer Bush heckled him in Brampton and sobbed joyfully as he made his victory speech after winning the leadership. They went public late last year. Over the holidays, they gallivanted around downtown most nights, shopping at the twinkly Distillery Christmas market, playing Ping-Pong at the gaming bar Spin, and bundling up to hear Kelly Clarkson and the Backstreet Boys at the I Heart Radio Jingle Ball. When Singh moves into his Trinity Bellwoods home later this year, Kaur will be joining him.
Spot Jagmeet at any party or event, and you’ll likely see his brother at his side. Gurratan is five years younger than Jagmeet and half an inch taller, with softer features, a slimmer build and the same fetish for elaborate custom suits. He used to run a criminal law practice in Peel Region but is gradually transitioning out of that world to serve as an adviser to Jagmeet. The Singh brothers spend more time together than most married couples: they go on vacations together (recent destinations include Costa Rica and Trinidad and Tobago, where Jagmeet took up surfing), train in Brazilian jiu-jitsu together (they hold pads for each other in the living room) and watch Netflix together (their favourite movies are Conan the Barbarian and the critically loathed Waterworld).
The brothers complement each other temperamentally, too. Where Jagmeet deals in utopian vision, Gurratan handles the administrative details. When Jagmeet gets swept up in a big idea, Gurratan offers a strategy. “He wants to see amazing, beautiful things, and I’ll be like, ‘Okay, but how do we do this?’ If he wants to do something now, sometimes I have to tell him it will take a couple of years,” Gurratan says. “He’s carefree, and I can be more pragmatic.” Gurratan does double duty as his brother’s conscience and his loudest cheerleader. “He’s Jagmeet’s rock. He supports him through anything,” says their friend Amneet Singh. “And Jagmeet is Gurratan’s hero.”
Jagmeet Singh has politics in his marrow. His ancestor Sewa Singh Thikriwala was a Punjabi martyr who fought for Indian independence in the early 20th century, and led uprisings against feudalism and colonialism in his home state, what is now known as Punjab. In prison, he went on a hunger strike and died of starvation, becoming a folk hero in the process. Jagtaran Singh—Jagmeet’s father—trained as a GP in Punjab and in 1977 moved to Scarborough, where he married a teacher named Harmeet Kaur. Jagmeet was born in 1979. His younger sister, Manjot, followed three years later (she’s now a stay-at-home mom in the U.K.), and Gurratan two years after that. The family moved around for a few years while Jagtaran studied to become a psychiatrist, working night shifts as a security guard. He heard that the city of Windsor needed psychiatrists, so in 1986 he packed up his family and settled in a comfortable suburban neighbourhood a 10-minute drive from the Gordie Howe International Bridge.
All of the Singh kids had received Anglicized names that their parents hoped would help them fit in at school—Jagmeet was known as Jimmy, Manjot was Mona and Gurratan was Gary. But when Jagmeet was eight, he declared that he wanted to go by his original name, to honour his heritage and his family. The decision was part of a larger embrace of his cultural roots. Jagtaran wasn’t an observant Sikh at the time—he ate meat and drank alcohol, kept his hair short and chose not to wear a turban. Harmeet, however, gently nudged her elder son toward spirituality, sharing stories about Sikh history and philosophy. “She’s the one who taught me most of the foundational stuff I believe in,” Singh says. “Like the fact that we’re all connected, that we all share something.”
When Singh decided to stop cutting his hair, his classmates responded savagely. They’d yank and twist it, calling him a girl. They’d sneer that his skin was brown because he was dirty and didn’t shower. The abuse got so bad that his parents pulled him from his class and enrolled him in Detroit Country Day School, a posh uniformed prep school whose alumni include Robin Williams and former Microsoft CEO Steve Ballmer. Every day, he drove 40 minutes across the border to attend school in Detroit, occasionally showing up late when there was a lineup on the bridge or a problem with his student visa.
As Singh’s mom fostered his spiritual growth, his father pushed him to succeed in Gatsby-esque activities like horseback riding, private tennis lessons and golf lessons. When he wasn’t practising his swing, he was devouring fantasy novels by Anne McCaffrey and Terry Brooks (he was a dragon expert before Game of Thrones) and watching Star Trek: The Next Generation. “I love that stuff. It helps you imagine another world, sometimes for better, and sometimes for worse,” he says. “How do you create unity without conformity and colonialism? How do you celebrate identities? How do you create a better society?”
Singh studied biology at Western, with the aspiration of becoming a doctor like his dad. In the summer, he stocked shoes at Aldo. As he got older, he took on a parental role with Gurratan, making sure his brother had lunches for school, introducing him to martial arts, teaching him how to work out at the gym. He even taught some of Gurratan’s friends how to tie their turbans like he did. Amneet recalls the Singh house as a place where the door was never locked, where there were always people coming and going. “I lived with them for weeks at a time,” Amneet says. “I’d wake up in the morning and Jagmeet would be making breakfast, and his mom would be cracking jokes, and his dad would be doing a yoga headstand.”
Toward the end of Singh’s undergrad program, he took an elective on the philosophy of law. Something clicked. His professor told him he had a talent for the subject and encouraged him to pursue law as a career. In 2002, he enrolled at Osgoode. As he studied the law, he got involved in the world of social justice. He attended protests to fight tuition hikes, and joined anti-poverty and advocacy groups to help refugees and immigrants exercise their rights. And he began to fight back against the discrimination he routinely experienced as a young man of colour. People would yell “Osama” at him when he walked down the street. When he used to borrow his dad’s Mercedes, he’d blast his favourite hip-hop tracks by Common and Dead Prez. Police would stop and card him, demanding to see his ID without cause. Soon, the same thing would happen while he walked around downtown Toronto. At first, he figured it happened to everyone, but when he asked his white friends, they told him they’d never been stopped. After graduating from law school, he sat in on a trial where the defence was cross-examining a cop for stopping a young black man. “I thought, ‘Hey, that seems like a pretty powerful thing to do. To be able to check and balance the power of police to make sure they’re doing their job appropriately.’ ” That’s when he decided to enter criminal law, later taking a job with Pinkofskys, now Rusonik O’Connor, Canada’s largest criminal law practice.
When I asked him if he’d struggled with the fact that his job required him to help set criminals free, he shifted the conversation toward the people whose rights he’d helped protect. He told me about representing a man who’d dug himself into so much debt that he started fresh under a fictional identity. He described the black men assaulted by police, the kids subjected to arbitrary searches. “My goal was not to defend someone who’d done something bad. My goal was to defend the idea that our liberty is so precious that it should only be taken away when we show evidence,” he explains.
The Jagmeet Singh who graduated from university is barely recognizable as the Beau Brummell we know today. Back then, he dressed in oversized velour tracksuits, XXL sweatshirts, combat boots and baggy jeans. “I was thugged out,” he says. “I wanted to convey strength in my style, so I tapped into a hip-hop aesthetic.” When he transitioned into his career, he still wanted to project strength, but in a way that was more professional. “In a space where I felt a bit powerless, I wanted to convey power. I wanted to discourage people who might want to treat me unfairly. That’s when I said, ‘It’s suits!’ ” He spent months studying the different cuts and fabrics, the lapel options and pocket placements. Eventually, he found his preferred English aesthetic. Within weeks of debuting his new look, prospective clients started approaching him in court and asking him to fight their cases. They wanted a lawyer with swagger.
By 2012, Singh was a minor Toronto celebrity. Street style photographers stopped him and Gurratan, shooting the brothers like GQ models, their sleeves artfully rolled, their faces conveying practised insouciance as they leaned against their retro fixies. Jagmeet had opened his own practice, Dhaliwal Law, and had parlayed his student advocacy work into a side hustle offering legal support services and know-your-rights seminars for students. The way he tells it, he had no political ambitions.
One day, Gurratan sat Jagmeet down and suggested he run for a federal seat in Parliament. “A lot of people want you to do this,” he told his brother sternly. “We don’t have an advocate to take these issues into the political realm. We want it to be you.” Jagmeet demurred. He didn’t want to be a public figure, to open up his life to the scrutiny of millions. He worried what kind of effect a political career could have on a future partner. And, most of all, he liked being an advocate, the insurgent upstart who put pressure on the government. “I was like, ‘I’m gonna fight the man.’ I didn’t want to be the man. Politics didn’t seem authentic to me.” Over the next few months, Gurratan and Amneet launched a two-pronged attack. Amneet fluffed Jagmeet’s ego, praising his charisma, his gregarious personality, his mentorship and leadership skills. “We knew that the guy was principled, that he was unwavering, that he wasn’t going to bend to the pursuit of power,” Amneet says. Gurratan laid the kind of guilt trip that would make any mother proud. “You’re letting us down,” he repeated to Jagmeet, again and again.
In March 2011, Singh finally relented and ran as the NDP candidate for the federal riding of Bramalea-Gore-Malton. He lost by some 500 votes. According to Gurratan, Jagmeet’s supporters felt a profound sense of guilt when they found out how close the race had been. When Singh launched another campaign later that year, this time for the provincial riding of the same name, his support base came out to the polls in greater numbers. He defeated his opponent—an eight-year incumbent—by more than 2,000 votes. “You reach a point when you have a generational shift, where you say, ‘The candidate we needed in the ’90s is not the candidate we need now,’ ” Gurratan explains.
Singh’s six-year tenure at Queen’s Park was steady, if unremarkable. His performance in the legislature didn’t quite match his flashy physical presence. Over the years, he tabled a few private member’s bills, among them a proposal to exempt turban-wearing motorcycle riders from the province’s helmet laws and a bill to reduce extortionate car insurance rates, both of which were quashed. In a prescient move, he was among the first MPPs to criticize Tarion, the government-created home warranty provider, for its apparent coziness with builders, and tabled a bill that would empower the provincial government to investigate the corporation. Soon after, provincial NDP Leader Andrea Horwath appointed him her deputy. His most explosive moment came in mid-2015, during the height of the carding crisis in Toronto. Singh took a vocal stand against the practice, all but accusing police of racism and condemning the SIU for its general opacity. He took the opportunity to open up about his own experiences with carding and discrimination, revealing the kind of unvarnished vulnerability that you rarely see from Canadian politicians. When he introduced a motion to eradicate carding across Ontario, it passed unanimously.
If Singh didn’t have a huge presence at Queen’s Park, he was getting attention everywhere else. In 2014, he smouldered in a black velvet blazer and gold Rolex for a fashion campaign for Yorkdale mall. He sashayed down the runway as a model at GotStyle’s fashion show in a floral jacket by Sand Copenhagen and shimmering black jeans. He perfected his social media strategy—for every obligatory Instagram photo of a constituent meeting or community event, there were two of Singh staring broodily into the middle distance in Cuba or Madagascar, dressed in slouchy leather jackets or Miami Vice whites. Last year, he and his suits got a feature in GQ, while BuzzFeed touted him as “the most stylish politician in Canada by like a million kilometres.” Singh was tickled.
When the NDP repudiated Tom Mulcair in 2016, several people on Singh’s team began whispering in his ear about the possibility of running for the party’s top job. Just as he had in 2011, Singh told them he was happy where he was. But over the following year, the idea grew on him. Justin Trudeau heralded a sunny, liberal, post-Harper future, but Singh didn’t buy it. “There’s something very likable about him. I even kinda like him,” he says. “But when it comes to making this society better, he’s not doing that.” He was particularly galled when Trudeau backpedalled on his promise of electoral reform. “If you come from privilege and you have power, it’s not a big deal. But without proportional representation, many disenfranchised people feel like their votes don’t matter.”
Finally, last spring, he committed to running for the leadership. Rather than appealing to the party’s existing base, his strategy was to expand it. He focused on two of the fastest-growing voting groups in Canada, and the people most affected by the widening income gap and discrimination: millennials and racialized Canadians. At Singh’s campaign office in Mississauga, volunteers and their families would take shifts cooking, preparing giant batches of vegetarian curries and rice for the team. Soon, hundreds of people were stopping by regularly. Kids would go home to their parents and tell them they had to take down their Liberal lawn signs and put up NDP ones instead. “Traditionally, in politics, the big two parties would reach out to the men, who made voting decisions in the family,” explains Amneet. “We were engaging mothers and young people. Instead of speaking to one person in the family, we were speaking to the other four.”
In his first few months as leader, Singh has made his way across the country, kissing thousands of babies. After resigning from Queen’s Park, he chose not to run in any of the six recent by-elections; he said that’s because he wants to run in the GTA or Windsor in 2019, but it’s more likely that losing a by-election would be more damaging than not running at all. Frank Graves, a pollster with Ekos Research, believes Singh’s failure to run is a major misstep. “Some people think this is clever politics, but it doesn’t make any sense at all,” he told me. “If you’re running for prime minister, you want to show your skills in the House. You want to be an MP.” Singh has also made a few minor blunders in his early days. He said he’d support Quebec separatism if the province voted for it—a strangely sovereigntist notion for a guy hoping to run the country. And when CBC interviewer Terry Milewski asked him to condemn the followers of Talwinder Singh Parmar, the Punjabi man widely believed to have been the architect of the 1985 Air India bombing, Singh claimed he had no idea who was responsible for the attack. Milewski’s question was troubling—he would have never posed it to Singh’s white opponents—but Singh’s fumbling response earned widespread criticism. Despite these rookie mistakes, Singh is generating an infectious frisson among young, change-seeking voters who want to upgrade to the middle class. He’s focusing on the buzzy issues of the day: identity politics, climate change and inequality. “So far, most populist politics in Canada have been steeped in resentment, isolationism and right-wing sentiment. We haven’t seen a potent progressive populist force,” Graves says. “Singh is presenting options like free pharmacare, free eye care, deeper taxation on the wealthy. That could catch people’s attention.”
Where Singh stands out is in his expansive reach. Today, he has 148,000 Instagram followers. His top competitor from the leadership race, Charlie Angus, has 571. Manitoba MP Niki Ashton, the campaign’s youngest candidate, has around 3,000. Singh’s social media feeds are a masterfully calibrated cocktail of fun and fashion, intermixed with political messages about carbon reductions and pay equity. His Twitter feed (125,000 followers) reads like a Chicken Soup for the Soul book, spouting inspirational truisms about equality and opportunities and, yes, love and courage. In a BuzzFeed video, he said he identified with the Game of Thrones character Jon Snow, taking the opportunity to draw comparisons between the King in the North’s fighting and leadership skills and his own. In a quirky CBC YouTube video, he showed audiences how he ties his turban every morning. Singh pitches himself as strong yet sensitive, principled yet goofy, charismatic yet humble. Just like Trudeau, he’s winning over voters with an utterly modern, deliberately relatable twist on the career politician.
In January, the NDP’s press secretary invited me to attend a dinner party, where Jagmeet would propose to Gurkiran. The event took place at Vegetarian Haven in Baldwin Village, the site of their first date. The place was tricked out with candles and pale-pink roses, an alcove at the front of the room draped in white curtains and sprinkled with rose petals. About 30 of the couple’s friends—along with a few members of the media—poured into the narrow space, eagerly awaiting Singh and Kaur’s arrival as a string quartet warbled out Ed Sheeran’s “Thinking Out Loud.”
When Singh and Kaur finally showed up, he got down on one knee, grinned, and quietly proposed, handing her a ring set with a honking sapphire and a band of diamonds. “Everybody, I’m engaged!” Kaur hollered. Within minutes, the news was on the Canadian wires. The next day, the NDP asked supporters to send congratulations through their website, presumably to gain potential voters’ contact info.
In just a few years, the young lawyer who feared the public’s scrutiny has become a slick politician who invites the media to his marriage proposal. Not only has he accepted his life in the public eye—he luxuriates in it, feeding off the accolades, the intrigue, the peacockery. But there’s more to his ubiquity than ego. He fosters intimacy with his voters, using social media to provide a peek into his daily life. For many Canadians, Singh’s glossy lifestyle is as much about representation and aspiration as about vanity. Because if a second-generation Sikh guy from Windsor can make it this far in Canada, so can they.
This story originally appeared in Toronto Life magazine. To subscribe, for just $29.95 a year, click here.