The Charm Of­fen­sive of Jag­meet singh

Catchy slo­gans, be­spoke suits and the mak­ing of a po­lit­i­cal su­per­star

Toronto Life - - Front Page - BY Emily Lan­dau


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 old­school 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.


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 starstruck 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.”


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.


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. ∫

Singh signed up some 47,000 new mem­bers en route to win­ning the NDP lead­er­ship with 54 per cent of the vote

Singh’s mother, Harmeet, fos­tered his spir­i­tu­al­ity. At age eight, he stopped cut­ting his hair and dropped his Angli­cized name

In grade school, Jag­meet was known as Jimmy. His brother, Gur­ratan, went by Gary and his sis­ter, Man­jot, by Mona

Singh flanked by his friends, the pho­tog­ra­pher Har­man Du­lay, the rap­per Fateh Doe, the vis­ual artist Bab­bu­li­cious, and his brother, Gur­ratan, dur­ing Nuit Blanche 2016

Jag­meet’s fa­ther, Jag­taran, worked nights as a se­cu­rity guard while study­ing to be a psy­chi­a­trist

Singh pos­ing with Gur­ratan for the street style blog Toronto Verve in 2012

On the runway dur­ing Toronto Men’s Fash­ion Week, Au­gust 2017

In Italy, July 2015

In the On­tario leg­is­la­ture, Oc­to­ber 2014

On New Year’s Eve, De­cem­ber 2016

With Bryan Adams, Jan­uary 2014

With the poet

Rupi Kaur, Oc­to­ber 2017

On his Bromp­ton fold­ing bike in Dart­mouth, N.S., Au­gust 2017

With de­sign­ers Dean and Dan Caten, Septem­ber 2014

With Jas­meet Raina, a.k.a. Jus Reign, at Fash­ion Week 2015

With Paul Ma­son, the Fash­ion Santa model, March 2017

Hik­ing in New Zealand, De­cem­ber 2015

With the rap­per Post Malone, De­cem­ber 2017

With Gurki­ran Kaur at Veg­e­tar­ian Haven restau­rant, the site of their first date, on the night he pro­posed

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