The Influentials 2019

From sports barons to tech titans, culture czars to rap stars: 50 power wielders who are changing the world as we know it

If you weren’t paying close attention, you might think 2019 was a year of subtraction. Doug Ford continued his cuts to public service, hollowing out many of the things that set Toronto apart. But while Ford was doing his best Mike Harris impersonation, a crazy thing happened: the city rallied in spite of him. Take Aliénor Rougeot, the 20-year-old U of T student who was so incensed by Ford’s stance on the environment that she and some friends organized a protest that drew thousands to the streets. Other magical things occurred, too: an obscure racquet-wielding Thornhiller defeated Serena Williams, twice; Scarborough’s Lilly Singh went from YouTube to late-late night; Schitt’s Creek blew up (in a good way); Margaret Atwood somehow topped her 2018, which somehow topped her 2017; and Sidewalk Labs finally got the go-ahead, for the moment anyway, on its funky-futuristic lakeside neighbourhood, causing euphoria in some corners and migraines in others (it’s probably a good thing that pot is legal). Of course, most magically of all, the Raptors, led by Masai Ujiri, came along and stirred up emotions we almost forgot we had, taking every tot, teen, mom, dad and grandparent on a spellbinding journey to the heart of the playoffs and emerging with the most beautiful thing we’ve ever seen: the Larry O’B, as it shall forever be known. Ford tried to cut us down. Ujiri lifted us up. For that reason, he’s our person of the year.

Photo by Markian Lozowchuk

Toronto Raptors President

1 We knew it five years ago, when he stood up in front of a crowd of screaming fans at Maple Leaf Square and blurted out “Fuck Brooklyn” before a Raptors-Nets playoff game: Masai Ujiri was going to do something big here. First he rebranded his team, then he rebranded Toronto. He made us feel worthy of a championship and then went out and got us one. If his decision to replace head coach Dwane Casey with assistant coach Nick Nurse was risky, his decision to trade the team’s best player—DeMar DeRozan—for one year of an injured Kawhi Leonard seemed like borderline lunacy. It not only worked, it delivered some of the most thrilling, unforgettable moments in Toronto sports history. But the Raptors president did more than just secure an NBA trophy. This year, Ujiri, more than anyone else, engineered a new Toronto identity: city of winners. Friends in high places: Barack Obama, Rwandan President Paul Kagame and Kenyan President Uhuru Kenyatta.

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Photo by Markian Lozowchuk


2 In his second year at Queen’s Park, our wrecking ball of a premier continued his assault on Toronto’s perceived profligacy. As 2019 dawned, Ford—deep breath—reduced OSAP eligibility for university students, threatened to fold 14 local health care networks into six agencies, eliminated 3,400 full-time teaching positions, slashed legal aid for refugees, cut $1 billion from Toronto’s transit plan and another billion from public health, and rolled back funding for stem cell research, artificial intelligence studies and environmental programs. And that barely gets us through May. Depending on your point of view, Ford was either implementing much-needed austerity or seeking vengeance on the city that scorned him. How he sees it? Wynne’s extravagance landed us in this mess and he’s trying to get us out. It hasn’t all gone to plan—his cannabis rollout lost $42 million and his carbon tax court battle with the feds cost $30 million and counting—but no amount of bad press will sway the loyalty of Ford Nation: as always, thousands of admirers showed up at Ford Fest like kids lining up to meet Santa. Up next: Implementing the Ontario Line, his sprawling transit plan.

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3 He may have kicked off 2019 with a shiny new Grammy for “God’s Plan,” but the rest of the year was all about empire diversification. In March, he reached a deal to rebrand the Raptors’ training facility as the OVO Athletic Centre. He intensified his presence courtside during the playoffs, where his theatrics got more airtime than many of the players. He produced the megahit series Euphoria on HBO, documenting the sexual and pharmaceutical escapades of Gen Z, and the show was renewed before Season 1 was finished. In August, he somehow found time to drop Care Package, a collection of unreleased tracks from the past decade, and, of course, it immediately soared to number one. Up next: Moving into his Bridle Path mansion, which is almost complete.

Photo by Markian Lozowchuk

Deputy Prime Minister

4 The enduring image of Freeland from 2019 was of her walking through Pearson airport in cherry-red running shoes, one arm around Rahaf Mohammed al-Qunun. The Saudi teen became an instant celebrity when she holed up in a Thai hotel room and refused to return to her home country for fear of death. Freeland believes it is Canada’s role to protect democracy and a rules-based international order. Jailing women and threatening teenage girls gets her back up. With so much of the world consumed by chaos and uncertainty, saving al-Qunun was part of her strategy to cement Canada’s reputation as a welcoming place—a haven from despots, discrimination and war. Up next: Settling into her new role as minister of intergovernmental affairs. The Liberals took a grand total of zero seats in Alberta and Saskatchewan this time around, so Freeland, who was born in Peace River, Alberta, will be charged with brokering peace in the Prairies, where anger about pipeline inaction runs high. Doing so without abandoning Liberal commitments to the environment will be the challenge. It’s a massive and complex task, which is why Trudeau put his most trusted lieutenant on it.

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5 Tory is the city’s best defence against the hack-and-slash whims of Queen’s Park: he led a successful charge to reverse $150 million in cuts to ambulance services and health and child care funding, and he launched a Supreme Court challenge against the premier’s near-halving of city council. Thankfully, Tory has a better rapport with the PMO—he wrangled $1.3 billion in federal funding for community housing and lobbied Trudeau to open the door for a handgun ban—and with his councillors, whom he convinced to approve 3,700 new affordable rental units and a gun buyback program that took 2,700 weapons off city streets. On top of making the city safer for the people who live here, he made it more attractive to people who don’t, touting our tech sector at SXSW and courting Netflix and Amazon to establish massive operations in Toronto (translation: nearly 2,500 jobs). In 2019, when no politician seemed immune to scandal or bouts of stupidity, it was a luxury to have a competent, drama-free workhorse in our corner. Up next: Green initiatives, including building retrofits and buying electric buses.

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6 Ask the MLSE execs who are now taking regular coin baths, Scrooge McDuck–style, and they’ll tell you extending Kyle Lowry for an extra year at $31 million (U.S.) was a bargain. Post–Larry O’B, ticket sales are booming (the wait list for season tickets is 10,000 seats long) and merch sales are too (the Raps were first in arena sales last season). Plus, given what Lowry has brought the city—a trophy, for one; a warm, lasting glow, for another—re-signing the beating heart of Raptor nation was a no-brainer. Charity circuit: Through their foundation, Lowry and his wife, Ayahna, provided Thanksgiving meals for 250 families at the John Innes Community Centre.

Photo by Markian Lozowchuk


7 By age 80, most of us will have settled into our easy chairs and yanked the recline lever. But the freshly octogenarian Atwood is at the height of her powers (Twitter followers: two million), her opinion sought on every vital matter, from #MeToo to climate change to the rise of totalitarianism. The Testaments, her eagerly awaited follow-up to The Handmaid’s Tale, was co-winner of the £50,000 Booker Prize in October and broke Canadian sales records immediately upon release. Like its predecessor, it will be a Hulu series from Emmy-winning showrunner Bruce Miller. Friends in high places: Twitter CEO Jack Dorsey and actor-comedian Rob Delaney.

Photo by Luis Mora

NDP Leader

8 Singh was the only leader whose reputation actually improved after the federal election. There were lots of reasons for the Singh Surge: his growing confidence, his unscripted nature, the deft manner with which he dealt with racists and his considerable appeal among young voters (Scheer definitely wasn’t making TikTok videos). While those qualities may not have translated into seats, the NDP holds the balance of power in a minority Parliament, and Singh can now push Trudeau on policy areas like pharmacare, affordable housing and climate action. Friends in high places: The pop star Rihanna is both an admirer of Singh and a follower on Instagram.

Photo courtesy of CBC


9 Becoming america’s buzziest “new” comedy involved a lot of legwork on this side of the border. The CBC show, which launched in 2015, got a major boost when it was picked up by Netflix two years later. The real secret sauce is the ensemble cast, starting with Eugene and Dan Levy, the father-son co-creators who play father and son onscreen. They came up with the concept of a Kardashian-esque clan who lose everything and must move to a town they once bought as a joke, and Eugene convinced his old SCTV pal Catherine O’Hara to play his wife. The Levys, plus O’Hara and co-star Annie Murphy, walked the red carpet en famille at the 2019 Emmys, where they were nominated four times, including a nod for O’Hara as best comedy actress. Levy Jr. earned a GLAAD media award for his show’s get-over-it approach to sexual diversity and signed a three-year deal with ABC/Disney to develop new TV projects. Up next: That sweet, sweet syndication money. Fox recently picked up the rights.

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Artistic Director, TIFF

10 He programs a movie festival that, in its 44th year, is the place to be screened and seen, with the most premieres, stars (Streep, Springsteen, Phoenix and Portman, among hundreds of others, in 2019 alone) and screaming fans. But Bailey’s true superpower is how he’s kept TIFF wonderfully progressive. Look beyond the Hollywood blockbusters and you’ll find obscure and delightful fare, including genre flicks about vengeful sea creatures, animated kids’ shorts and countless reels by that rarest of species, female film directors. Up next: Coordinating Share Her Journey, a women-in-film program with ambassadors including Jennifer Baichwal, Jill Soloway and Priyanka Chopra.

Photo by Erin Leydon

Chairman, Waterfront Toronto

11 He spent the past 11 years erecting buildings beloved by buyers and planners, like the Well at Front and Spadina. All three levels of government asked him to navigate Toronto’s trickiest real estate quagmire: Sidewalk Labs’ smart-city proposal. When Sidewalk released its 1,524-page cinderblock in June, Diamond praised the buzzy ideas but pointed out that Sidewalk was overstepping in its bid to develop the entire Port Lands instead of the 12-acre plot they’d originally pitched. In late October, Diamond and his colleagues reached a hard-won deal to scale back the scope. Side gigs: He sits on the board of directors of Sunnybrook Hospital.

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Tennis Player

12 She started the season ranked 152nd in the world, a virtually unknown Canadian teenager who said her dream was to crack the top 50. And then she just kept winning—taking down the game’s greatest players with a power serve and serious mental mojo (she meditates daily). By October, after beating Serena Williams twice, she was fourth. Andreescu is the first Canadian to win a singles Grand Slam and may just be the next G.O.A.T. Up next: She’s got her eye on the 2020 Olympics in Tokyo.

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Chairman, MLSE

13 There’s a reason Tanenbaum—not Kawhi or Kyle—was first in line to hoist the Larry O’Brien Championship Trophy. As chairman and quarter owner of the $2-billion MLSE empire, he’s the most powerful sports figure in Toronto and the architect of the city’s recent athletic domination: TFC and the Argos were champs in 2017, the Marlies a year later and the Raps after that. Thanks to Tanenbaum’s commitment to a long-term rebuild, the Leafs might be next. Side gig: Through his private equity firm, Kilmer Van Nostrand, he sold the terminal at Billy Bishop, as well as 23 Onroute highway service stops—reportedly netting several hundred million dollars.

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Talk Show Host

14 “We are going to have the best time ever or my name isn’t Bisexual Woman of Colour!” That’s how Singh, a proud Scarborough native, closed the opening monologue of her new late-night talk show—the payoff to a crack about how the coverage around her appointment had been so focused on what she is not (i.e., white, male, straight and—by the way—American). Since becoming one of YouTube’s top 10 earners, she has gone by many monikers, including Superwoman and Bawse (she wrote a book about how to be one). The only “Donald” you’ll hear about on her show, says Singh, is Glover, but that doesn’t mean she’s shying away from sharing her opinions on the issues she cares about, like paid parental leave, breastfeeding in the workplace and gender diversity, all topics mentioned in the first five minutes of her premiere. The fact that she expressed them in a rap tells you that she may now go by Lilly, but she’s still a bawse. Friends in high places: Mindy Kaling and the Rock are close friends.

Photo courtesy of Penguin Random House

CEO Penguin Random House

15 Early in the year, Cochrane published a gorgeous new hardcover graphic novel version of The Handmaid’s Tale, and that was merely a prelude to The Testaments, Atwood’s long-marinating sequel. In its first month, Testaments sold more than 100,000 copies—obliterating sales records—and was quickly optioned by Hulu. But Cochrane isn’t satisfied with riding the Gilead wave. She brought ex-FLOTUS Michelle Obama to Toronto twice in 2019 in support of Becoming, which has sold more than half a million copies in Canada alone, and will release Obama’s companion journal this winter. Cochrane launched an imprint, Strange Light, for experimental literature, and one of its first titles, Max Porter’s dark fairy tale Lanny, was longlisted for the Booker. Up next: A new novel from John Irving, his first since 2015.

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Head Coach, Toronto Raptors

16 On paper, it was a curious move: firing Dwane Casey and putting the fate of the Raptors in the hands of his assistant, who’d never coached an NBA game. But Nurse, who had led 15 teams in five countries over 30 years, quickly earned a reputation as a calm, imaginative strategist. When he employed an unorthodox defensive strategy to contain and frustrate Steph Curry in the finals, purists mocked Nurse for the move, but the guy with the ring gets the last laugh. Up next: Preparing Team Canada for the Olympics. As head coach, he has committed to help recruit some of Canada’s best—including Andrew Wiggins and Jamal Murray.

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Pop Star

17 Everyone knew it would take a monster song to supplant “Old Town Road” as the song of the summer. That megahit came courtesy of Shamila, a.k.a. Shawn Mendes and Camila Cabello, whose Latin-infused duet “Señorita” was the season’s steamiest makeout track. (They nabbed a trophy for best collaboration at the MTV Video Music Awards.) August was an all-around great month for Pickering’s favourite mop-top, who shed his boyishness—not to mention his clothing—in Calvin Klein’s latest ad campaign. Charity circuit: In August, he launched his foundation with $1 million (U.S.) for SickKids and Reverb, an environmental non-profit.

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Ontario Minister of Health

18 As deputy premier and health czar, Doug Ford’s chief rival has become his enforcer. When Ford wanted to reel in health care costs, he turned to Elliott to help shave half a billion in OHIP services by rolling back millions of dollars for cancer-screening programs, public health funding and stem cell research. Her most ambitious initiative is Bill 74, which would amalgamate several public health agencies into a super-agency called Ontario Health. Up next: Elliott is working to fulfill Ford’s promise to eliminate hallway medicine; the crisis hit a record high in Ontario in June.

Photo courtesy of 48North

CEO and Director, 48North

19 Gordon grows her own plants at home, and lights up three or four times a week, so she knows what cannabis users want from their weed. She markets cannabis as a wellness product, selling organically grown pot and handsomely packaged paraphernalia. In May, she received approval for a 100-acre outdoor cannabis farm near Hamilton, the largest licensed operation of its kind in Canada. This year alone, she raised $42 million in funding, acquired the popular vape company Quill and entered into lucrative wholesale agreements with Ontario, Alberta and Quebec. Side gig: Gordon co-founded the Helene Comay Nursery School at Wychwood Barns Park.

Photo by Daniel Ehrenworth

Self-Help Author

20 Where the clinical psychologist turned culture warrior goes, controversy follows. In the spring, the University of Cambridge revoked an invitation to be a research fellow; in the fall, Carlton Cinema dropped a screening of The Rise of Jordan Peterson. But none of it made a difference to his supporters, who hooted and cheered at his sold-out debate with philosopher Slavoj Žižek this April, then flocked to his YouTube channel—2.3 million subscribers—to watch the highlights. His pull-up-your-socks self-help manual, 12 Rules for Life, held fast on Amazon’s most-read non-fiction list all year long, with four million copies sold. Up next: A mysterious project that he’s working on with the National Post.

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Style Advisor

21 Jessica Mulroney has remained a key member of the Duchess’s inner circle, attending her super-glam NYC baby shower, co-hosted by Serena Williams and Amal Clooney, and defending her royal friend against racist bullies on Instagram. Mulroney was the subject of a feature profile in Harper’s Bazaar, appears regularly on Good Morning America as a style correspondent and has emerged as more than a mere royal accessory—a queen-maker in the fashion scene and maybe the world’s best bosom buddy. Up next: Hosting a Bell/Netflix wedding series called I Do, Redo, where couples who didn’t get it right the first time get a do-over.

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Inspector, Homicide Unit, Toronto Police

22 Idsinga started 2019 with a triumph: Bruce McArthur, the serial killer he apprehended, received a life sentence for eight counts of first-degree murder. It was a career-defining moment, and as a reward, the 30-year police veteran was named head of the homicide squad. He’s overseeing a new missing persons unit and a pilot video unit designed to extract footage from crime scenes, parse it and prep it for court, a tool that was used to solve the McArthur case and to reconstruct the 2018 Yonge Street van attack. Charity circuit: He participated in the inaugural Peloton Ride in September to support men’s mental health.

Photo by Daniel Ehrenworth

Chief Scientific Advisor, Vector Institute

23 Earlier this year, HSBC opened an AI lab in Toronto, joining companies like Uber, LG and Google. Credit Geoffrey Hinton, whose mere presence has transformed Toronto into a magnet for the AI techies who deify him. In March, along with two other AI pioneers, he was presented with the $1-million Turing Award (a.k.a. the Nobel Prize for computing). Inspired by Hinton’s research, Heather Reisman and Gerry Schwartz donated $100 million to U of T to create a new facility focused on AI research. Friends in high places: His former students include Yann LeCun, chief AI scientist at Facebook; Zoubin Ghahramani, chief scientist at Uber; and Ilya Sutskever, co-founder and chief scientist at OpenAI.

Photo Courtesy of WCH

CEO and President, Women’s College Hospital

24 In June, Women’s College became the first public hospital in Canada to offer a procedure that inverts a penis to create a vagina. The program is one of several initiatives under McPherson, the hospital’s newly minted head honcho, who is working to close the gaps that exclude marginalized Torontonians from health care. McPherson, who was previously the hospital’s VP of patient care, has also kick-started an Indigenous health program that provides safe spaces and culturally inclusive services to Indigenous patients, including cancer-screening programs that incorporate traditional healing activities. Charity circuit: She’s chair of the board of Planned Parenthood Toronto.

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City Councillor

25 Cressy sits on so many city committees you have to wonder if he ever sleeps. As the mayor’s designate for Waterfront Toronto, for example, he gets one of the deciding votes on Sidewalk Labs’ proposal. As a member of the Economic and Community Development Committee, he fought a city plan to cut funding for child care costs. Most critically, as chair of the Toronto Board of Health, he’s emerged as the city’s most vocal crusader against the province’s health care cuts. Up next: Securing council approval for climate change mitigation measures on the Toronto Islands and finalizing plans for the long-promised Rail Deck Park.

Photo by Craig Boyko

CEO, Art Gallery of Ontario

26 He’s the pied piper of Toronto, dreaming up scheme after scheme to entice the under-30 crowd to his 119-year-old museum. First, he raised $2.3 million to purchase one of Yayoi Kusama’s Infinity Rooms, securing a steady rush of selfie-starved visitors. Then he introduced a $35 annual pass and made admission free for anyone 25 and under. The move has already led to 100,000 new passholders, with a notable spike among Gen Z. He replaced the long-running First Thursdays party with a new festival called All Hours, featuring food, live music, installations and tipsy art crawls, running thrice yearly. To paraphrase Mean Girls: the AGO isn’t a regular museum, it’s a cool museum. Up next: In 2020, Jost mounts a show on Picasso’s Blue Period—the first of its kind in Canada.

Photo courtesy of Mattamy Homes

Founder and CEO, Mattamy Homes

27 In June, Gilgan donated $100 million to SickKids, the largest gift the foundation has ever received. The funds will help redevelop the 70-year-old campus, including the construction of a new family-care tower on University Avenue. Factor in Gilgan’s previous gifts—$40 million to SickKids in 2012 and $30 million to St. Mike’s in 2014—and he’s a literal lifesaver: no one has donated more to Canadian health care. Friends in high places: Outgoing TD exec Tim Hockey, venture capitalist John Ruffolo and ETF pioneer Som Seif all participated in Gilgan’s Tour de Bleu, an annual cycling event that raised $4.4 million for CAMH in 2019.

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28 If last year’s “ultimate glam wedding involving a Toronto person” went to the Duke and Duchess of Sussex, this year’s title goes to Canadian YouTube queen Gigi Gorgeous, who grew up in Mississauga, and socialite Nats Getty (yes, those Gettys). The beachside nuptials—a fairy-tale fantasy in Montecito—came just three months after the release of Gorgeous’s 2019 memoir, He Said, She Said, which chronicles her gender transition. It’s a journey fans (more than seven million across social media) started following a decade ago when she began uploading videos to YouTube. Today, Gorgeous is among the loudest and fiercest voices in LGBTQ activism, one of the most influential people on the Internet according to Time magazine, a Revlon beauty ambassador and most recently, the grand marshal of last summer’s Pride Parade. Friends in high places: Caitlyn Jenner, Lady Gaga.

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29 It’s not easy to steal a scene from Julia Roberts. But playing opposite America’s sweetheart, that’s exactly what James did, turning in a Golden Globe–nominated performance as a recovering military vet in Homecoming. He also starred in rom-dram If Beale Street Could Talk and recently landed the cover of Variety’s annual Young Hollywood issue. This month, he plays the bad guy in 21 Bridges, a crime thriller starring Chadwick Boseman, who had better hold on to his scenes for dear life. Up next: Season two of Homecoming, in which Janelle Monáe joins the cast.

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Chairman, Thomson Reuters

30 Thomson’s net worth of nearly $50 billion is three times higher than that of Canada’s next-richest person. His flagship, Thomson Reuters, shed a majority stake in its finance and risk business, Refinitiv, to private equity firm Blackstone Group for $21.8 billion, and posted its best revenue growth in over a decade. Now the news and finance-info behemoth is pushing its chips toward AI, launching Checkpoint Edge (a smart tax-guidance platform) and Westlaw Edge (an AI-fuelled legal and research tool). Up next: Thomson’s real estate firm, Osmington, promises—promises!—that the Union Station overhaul will wrap up next fall, a full decade after it began.

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Governor of the Bank of Canada

31 Some 68 per cent of Canadians own their own home, and a scary-big chunk, especially in Toronto, could be in trouble if Poloz ever leans on the big red interest rate button in his office. Thankfully, he’s a careful guy. Since taking on the gig in 2013, Big Gov has ever so gently upped the key rate, edging the market back to normalcy while keeping homeowners solvent. He’s done well, especially with half his tenure coming with a drunk driver behind the wheel of the world’s most powerful economy, a guy who sparks trade wars with major powers and subtweets his own Federal Reserve (43 times in six weeks), all of which complicates Poloz’s already complicated job. Up next: Headlining the OSC’s annual conference, Dialogue, this month.

Photo courtesy of Wattpad

Founders, Wattpad

32 There often comes a point in the lifespan of a successful start-up when it circles back to doing just the thing it disrupted in the first place. In the case of Lau and Yuen, who founded Wattpad as a hub for user-generated stories, that means publishing real, flippable, paper-bound books: their first six YA titles hit stores this fall. Sony recently inked a deal with the company for first dibs on any of their 500 million stories for TV development, and Entertainment One is bringing in Wattpad superfans as consultants for scripts they’re developing based on content that debuted on the site. Side gigs: Unintentional movie executives. A Wattpad-produced film based on One Direction fan fiction debuted in theatres this year, and brought in $70 million at the box office.

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33 Saying goodbye is never easy, but the Donaldson-Bautista-Encarnación-shaped hole in Jays fans’ hearts has been quickly filled by a trio who have the potential to be even better. They’re all the kids of former all-stars and have shown they’re comfortable in the spotlight. Having ascended through the minors together, they’ve become close friends, a bromance that spawned the nickname the Blue Genes. So far, Guerrero has endorsement deals with Under Armour, Louisville Slugger, Amex, BioSteel, TD Bank, Topps, Panini and Leaf. Charity circuit: They’re supporters of the Jays Care Foundation, which raised $10 million for kids in need in 2019.

Photo by Aaron Wynia

Chief Information Officer, BMO

34 In September, McGowan was tapped to interview Michelle Obama onstage at the Elevate Festival, a nod to her immense smarts, reputation as a clear communicator and sterling resumé. She launched the Black Arts and Innovation Expo in 2015, a job fair and scholarship program that helps black candidates get good jobs in STEAM. Two years later, she spearheaded BMO’s Women in Technology program, which supports female entrepreneurs and boosts the number of women on boards; at BMO, women fill 40 per cent of senior leadership roles. Up next: Heading up BMO’s new campus at Yonge and Dundas, which will house 3,500 employees as soon as 2021.

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Chief Marketing Officer, MLSE

35 There are only a few people who can snap their fingers and inspire millions to buy the same thing. Meghan Markle is one. The Kardashians are three. And a fifth is Shannon Hosford, the marketing guru responsible for rolling out We the North, the branding campaign that galvanized not just the Raptors but the city itself, reshaping our self-image as strapping, winter-hardy Starks. If Masai turned the Raptors into winners, Hosford made them cool. This year, she won her own championship: the ACA Gold Medal—the Oscar of Canadian marketing. Up next: For the team’s 25th anniversary, Hosford is debuting her next big campaign: a pair of hands, one holding up two fingers and the other holding up five. Get ready to see it everywhere.

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CEO, Paramount Fine Foods

36 Running the fastest-growing Middle Eastern restaurant chain in North America is how Fakih finances his greater passion: saving the city from the forces of evil. Last year, Fakih donated $25,000 to the Canadian Anti-Hate Network. Then, in the spring, he emerged victorious in a lawsuit against a racist YouTube ranter, who was ordered to pay $2.5 million in damages. More recently, he stepped in to help the owners of Soufi’s Syrian café after online bullying and death threats forced them to close. Fakih, who has hired refugees at his own restaurants since 2015, offered his own staff and security to ensure the restaurant’s survival. Friends in high places: Justin Trudeau and Raptors superfan Nav Bhatia.

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37 This year, nearly two decades after bailing on a hostile bid for Air Canada, Gerry Schwartz and his private equity firm, Onex, finally got in the airline game with the purchase of WestJet for $3.5 billion. At Indigo, Reisman lured Nathan Williams of the minimalist lifestyle magazine Kinfolk back from Denmark to oversee a new creative direction for her cultural department store. Charity circuit: In March, the couple announced a $100-million gift to U of T for research in AI, biomedicine and the intersection of tech and society.

Photo by Aaron Wynia


38 The guy who “puts the tattoo in ratatouille,” as Jimmy Kimmel put it, released his first cookbook, an eponymous blend of recipes and reflections that landed on the NYT bestseller list. In the summer, he brought his Matty’s Patty’s event on the road. (Turns out Matheson is big in Japan, too—they sold out of 500 burgers in the first few hours). In September, he launched MattyFest, a punk, rap and food festival featuring his favourite bands and fellow Toronto chefs. And his new YouTube cooking series, Just a Dash, makes his old show look low-key by comparison. Up next: A still-unnamed restaurant at Queen and Shaw, a clothing line and a podcast.

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Co-founders, HXOUSE

39 Improving the odds that more The Weeknds emerge in Toronto is the mission of HXOUSE—a new creative hub launched by Tesfaye and his friends Taylor and Ismail. The concept applies the tech-world incubator model to raw artistic talent. Last fall, more than a thousand would-be Weeknds applied for a handful of spots in HXOUSE’s inaugural scholarship program—a year-long placement that connects young people with world-class equipment and instruction from both a creative and entrepreneurial perspective. Recent grads have scored gigs with Xbox and Twitter. Up next: Expansion. HXOUSE will soon unveil its plans for international growth.

Photo courtesy of GFL

CEO, Green for Life

40 The “one man’s trash” jokes write themselves. But the trajectory of Dovigi’s waste-management company, Green For Life, is no laughing matter: in the eight years since he nabbed a huge chunk of the city’s garbage routes, he has dispatched his lime-green trucks into nine provinces and 23 U.S. states, pulling in $2.7 billion in revenue last year alone. Having acquired more than 100 waste companies, Dovigi shifted his sights this summer from black bin to blue, snapping up Canada Fibers, Ontario’s largest recycling operation. Any minute now, he’ll launch an IPO that’s expected to be worth around $2 billion. Charity circuit: In June, Dovigi, who was drafted in 1997 as a goalie by the Oilers, donated $5 million to the Sinai Health System for a sports-medicine clinic, helmed by the Jays’ and Leafs’ orthopaedic doctor.

Photo courtesy of CBC

CBC Radio Host

41 As host of Here and Now and then Metro Morning (not to mention numerous Olympics and Sounds of the Season broadcasts) Matt Galloway has long been CBC Toronto’s most intelligent radio voice. Depending on his mood, he could be soothing or stern; depending on his guest, he could be playful or prickly. Next year, that voice will be heard coast to coast as Galloway becomes the new host of The Current, the popular current affairs program helmed for the past two decades by Anna Maria Tremonti. More than just a bigger platform, the show will allow Galloway to work his interviewing magic on boldface guests and national and international topics. Side gigs: He sits on the board of the Canadian Journalism Foundation.

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CEO, Loblaws

42 With more than a third of the grocery market share, Loblaws has the power to determine what Canadians eat—and Galen Jr. wants us to eat green. His PC label released more than a dozen new vegan products this year, including dairy-free cheesecake, egg-free mayo, a pea protein–based Undeniable Burger and a cricket protein powder, too. In April, Loblaws received $12 million from the feds to overhaul the refrigeration in 370 stores to reduce greenhouse gas emissions. Going green evidently helps with the black: Loblaws revenues are up some $300 million this year. Up next: Eataly mania. The Westons are part owners of the food emporium in the Manulife Centre.

Photo courtesy of OFH

CEO of Options For Homes

43 Tremain oversees a non-profit organization that is part developer and part real estate fairy godmother—she provides solutions to the affordable housing crisis. Options kicks in as much as 15 per cent of the value of one of their condos (buyers pay the other five per cent), then reclaims the same percentage when the owners sell. These shared-equity loans caught the attention of the feds, who brought Tremain in to advise on their First-Time Home Buyer Incentive, a strikingly similar model that took effect in September. Up next: Construction on Options’ Weston Village development, where 60 per cent of the 232 units are family-sized.

Photo courtesy of Simon and Schuster


44 The week before his memoir was published this August, it had already landed on the Globe and Mail’s bestseller list. Little wonder: in From the Ashes, Thistle, a Métis-Cree writer, chronicles his remarkable journey from the foster system through addiction and homelessness to a thriving academic career at York. Thistle’s story also provides painful context for his academic work at the Canadian Observatory on Homelessness. Side gig: This year, he became the newest board member of the Canadian Alliance to End Homelessness.

Photo by Getty Images


45 For further proof that Toronto is the breeding ground of hip-hop gods, see the 2019 explosion of this Drake producer turned Weeknd protégé turned Billboard-topping rapper whose latest album, Bad Habits, debuted at number one this spring. Navraj Singh Goraya grew up in Rexdale to Punjabi parents (he has described himself as “the first brown boy to get it popping”) and scored his break after appearing on a Weeknd-collab diss track of Bieber. This summer, his concert had to be relocated from Rebel (capacity 3,750) to Echo Beach to accommodate demand. Friends in high places: Bey and Jay. Nav produced their 2018 track “Friends.”

Photo courtesy of Bell Media

President, Bell Media

46 Most TV execs spent 2019 hiding under a desk, praying that the next disruptive whatever would pass them by. Lennox has been too busy to fret. His secret isn’t exactly revolutionary: he pays up for big hits (Game of Thrones and Succession, for two), and it’s worked: Crave had more than 2.7 million subscribers this year. On the TV side, the Raps run and Andreescu’s star turn helped spur five straight quarters of ad revenue growth. Lennox was executive producer of TIFF’s opening-night documentary, Once Were Brothers, a David Foster doc, and Clive Owen’s The Song of Names. Side gigs: He chairs the board of the Banff World Media Festival. In June, he hosted ex-Disney bigwig Jeffrey Katzenberg for a talk about his mobile streaming service, Quibi.

Photo by Evaan Kheraj


47 Canada’s most relentless and recognizable defence lawyer—she of the Tim Burton hair and chemical-spill-blue nails—is not known for her subtlety. The woman who has represented Jian Ghomeshi, Michael Bryant and many others vindicated her latest high-profile client, Vice-Admiral Mark Norman, in May. In a recent interview, she said that her reputation as the Hannibal Lecter of the courtroom is wrong—she’s more controlled and deliberate. She might be more intimidating, too. On election night in October, she took a star turn as a guest analyst on a CBC politics panel. Charity circuit: Henein recently performed a stand-up comedy set as part of the Humour Me fundraiser, benefiting SickKids.

Photo by Getty Images


48 Between 2005 and 2009, women in a tiny Mennonite colony in Bolivia would wake up bloody and sore, with no memory of what had happened to them. They discovered that men in the community had been drugging and raping them. This horrific legacy forms the germ of Toews’s Women Talking—a blistering nightmare and rallying cry against systemic sexual assault and religious fundamentalism. The book spent 23 months on the bestseller list, received gushy profiles in the New Yorker and New York Times, and became the first blockbuster #MeToo novel. Up next: Brad Pitt optioned the film rights. Frances McDormand will star.

Photo by Steven Lee


49 Salm’s 10 restaurants aren’t Toronto’s absolute fanciest or most cutting edge, but they’re exactly where you want to go for a big night out. His newest are Planta Queen, which serves delicious dim sum that’s 100 per cent vegan, and Arthur’s Restaurant, a cavernous and glittery series of rooms that make midtown glam. What ultimately sets his empire apart is that no matter how big it grows, each spot is deeply personal—especially Arthur’s, named after his father and inspired by his tastes, right down to the martini list. Charity circuit: Salm is a SickKids Innovator, part of a group that has so far raised nearly $1 million for the hospital’s pain and therapeutic programs.

Photo by Getty Images

Internet Sensations

50 The tans are fake but the struggle—raising seven kids between them—is real for Catherine Belknap and Natalie Telfer, who soared from low-profile mommy bloggers to global sensations overnight. What began as YouTube confessionals on topics like sex-after-baby spawned regular appearances on the Today show, sold-out appearances in Toronto then a tour—Minneapolis, Tampa, Houston—with the electric energy of a Taylor Swift show. Their 2019 book, Mom Truths, hit the bestseller list this spring, prompting a second set of tour dates. Up next: Mum’s Night Out—they’re taking their show to the U.K. in early 2020.

31 other Torontonians who are making amazing things happen




Climate warriors, powerful protesters and good Samaritans

Naomi Klein

In On Fire, Klein backs Alexandria Ocasio-Cortez’s demand for a Green New Deal in the U.S. (an idea Klein kinda-sorta invented with the Leap Manifesto in 2015). The book is a radical polemic for sweeping and probably unpopular policy changes—our only chance to change our habits, attitudes and futures. It quickly became a New York Times bestseller.

Aliénor Rougeot
Activist and Student

Toronto’s answer to Greta Thunberg is a 20-year-old economics and public policy student at U of T. Rougeot runs the Toronto branch of Thunberg’s Fridays for Future movement, and she helped organize, publicize and lead September’s explosive, city-stopping climate strike, where tens of thousands of protesters flooded the streets.

Geoff Cape
Evergreen Brick Works

At the Brick Works, Cape just opened the kiln building, a carbon-neutral event space using reclaimed rooftop rainwater for the toilets and irrigation, and geothermal pipes for heating. Appropriately, the site hosted the Future Cities Conference for urban and environmental leaders to pitch their plans for a greener tomorrow.

Nick Saul
CEO, Community Food Centres Canada

Rising temperatures are one of the driving causes of global hunger: farmland is degrading, water is drying up and crops are failing. Saul, who was appointed to the Order of Canada this year, recently opened three new food centres, and is planning to open three more in the coming months: one in Toronto, one in Saskatchewan and one in Iqaluit.

Catherine McKenna
Minister of Infrastructure and Communities

As minister of environment, she rolled out one of the world’s most dramatic carbon-pricing programs, projected to cut Canada’s emissions by up to 60 million tonnes by 2022. She also announced a single-use-plastic ban, committed to a national flood insurance program and funnelled $420 million to Ontario businesses to help fund energy-efficiency programs.



Silver-screen movers and shakers

Guillermo del Toro

The guy who helped resuscitate the city’s film industry is still showing love to his adopted hometown: he wrote and produced the Toronto-shot horror flick Scary Stories to Tell in The Dark, curated a Mexican film festival at the Lightbox and, this winter, will film a remake of the ’40s classic Nightmare Alley, starring Bradley Cooper.

Dahvi Waller

The TV veteran, who was a producer and writer on Mad Men and Halt and Catch Fire, spent the year creating your favourite new show of 2020: Mrs. America, which filmed this summer in Toronto and stars Cate Blanchett as Phyllis Schlafly, the bouffanted social conservative who lobbied to block the Equal Rights Amendment in the 1970s.

J. Miles Dale

Dale, who’s been financing films in Toronto since the early 2000s, is Del Toro’s most trusted local collaborator—they first teamed up on Mama in 2013 and shared Best Picture honours for The Shape of Water. Dale is handling producing duties on the horror film Antlers, which was shot this year and stars Keri Russell and Jesse Plemons.

Mike Bruce, Robbie David & Jeff Anders
Partners, Aeon Studio Group

The studio boom has crept west to Hamilton. Aeon will construct two million square feet of live-work-play space for creative industries, including 500,000 square feet of sound stages and facilities for post-production, animation and visual effects. The first few stages are expected to be open by summer 2020.


Exciting faces to watch

Simu Liu, 30

Liu, who plays Jung on Kim’s Convenience, has long been beloved for his charm, wit and six-pack abs. All three (or eight) of these things helped Liu land the titular role in the upcoming Shang-Chi and the Legend of the Ten Rings, Marvel’s first superhero movie with an Asian lead.

Ashley Audrain, 37

Write what you know, they say. And this publicist turned author wrote her first novel, The Push, a psychological drama about the complexities of motherhood, while she was on maternity leave. The book sold in 23 countries in just two weeks, setting an industry record.

Maitreyi Ramakrishnan, 17

The Mississauga teen beat out 15,000 other aspirants from around the world to be cast as the lead in Mindy Kaling’s new Netflix comedy series, Never Have I Ever. The show was inspired by Kaling’s own experience, but the bubbly and broadly talented Ramakrishnan will surely make the role her own.

Brittni Donaldson, 26
Assistant Coach, Toronto Raptors

Sure, we lost Kawhi, but behind the bench, the Raptors have only gotten better. Already a secret weapon in the front office, former data analyst Brittni Donaldson was promoted to assistant coach this season, becoming just the 10th woman to hold such a position in the NBA.

Satish Kanwar, 33
GM and VP of Product, Shopify

Kanwar sold his design firm, Jet Cooper, to Shopify back in 2013, then stayed on and set about establishing a presence in the GTA. You might say he’s delivered: HQ has dropped $500 million to double its staff to 1,500, open a 180,000-square-foot office space on King West and create a Front and Spadina space that’ll be even bigger.


Ascendant designers who are shaking up the industry

Noura Sakkijha

Selling low-key, cool-kid basics direct to consumers (including Oprah and Timothée Chalamet) has turned Sakkijha’s label, Mejuri, into a major industry player. She scored $31 million in a second round of funding last spring. In October, she won the DesignThinkers 2019 award for excellence in design.

Bojana Sentaler

Yes, there was an official launch for Sentaler’s 10-year anniversary collection, but the more significant PR moment came when long-time fan Meghan Markle wore the label’s poppy-red wrap coat as part of her fashion-forward maternity wardrobe. She wore that same coat in camel to her first Christmas at Sandringham.

Lesley Hampton
Lesley Hampton

When Hampton cast an amputee in one of her shows, Kim Kardashian called it “inspirational.” The most memorable moment of Fashion Week 2019 came when First Nations beauty queen Ashley Callingbull closed Hampton’s show in a gown adorned with red dots to represent missing and murdered Indigenous women.

Aurora James
Brother Vellies

The Toronto-raised, Brooklyn-based designer of funky, sustainably produced accessories won the prize for best International Canadian Designer at this year’s CAFAs. That same month, she dressed Nicki Minaj’s feet (strappy sandals) for the Met Gala and attended the year’s biggest fashion party herself.

Dani Reiss
Canada Goose

The guy behind Canada’s most ubiquitous fashion statement has gone global, launching Canada Goose in Asia last year then opening stores in Milan and Paris. Reiss, who recently made the Forbes billionaires list, launched Project Atigi (Inuktitut for parka), which commissions coats from Inuit seamstresses.

Kirk Pickersgill & Stephen Wong
Greta Constantine

Catherine O’Hara and Amy Poehler presented at the Emmys dressed by Pickersgill and Wong, the Canadian design duo known for making statements with solids. A long-time favourite with local fashion plates, the brand now counts Mindy Kaling and Lucy Liu among its “Greta Girls.”


Silicon Valley North’s biggest names

Dan Doctoroff and Alyssa Harvey Dawson
CEO and General Counsel, Sidewalk Labs

Sidewalk’s execs never said getting a high-tech community built would be easy, but they probably didn’t think it would be this hard. The controversy hasn’t deterred them, however. They’ve recently reached an agreement with Waterfront to continue the exploratory process.

Paddy Cosgrave
CEO, Web Summit

He’s the brains behind three of the world’s premier tech conferences: Web Summit in Europe, RISE in Asia and Collision in North America. When Collision outgrew its New Orleans digs last year, he chose Toronto. The 2019 conference drew 25,000 attendees and keynote speakers Justin Trudeau and Timbaland, and cemented the city’s rep as a global tech hub.

Denis Nagasaki
Principal Officer (interim), Silicon Valley Bank of Canada

Back in March, California-based SVB—the world’s dominant player in innovation financing—received a licence to operate in Canada. Nagasaki, a 30-year-old Ivey graduate, will lead the charge here, helping promising start-ups raise venture capital and grow their businesses.

Tamir Bar-Haim
Director of International Expansion, Amazon Advertising

Bar-Haim established himself at Amazon’s Seattle HQ, developing platforms to sell everything from clothes to jewellery to fine art online. Now, from his home base in Toronto, he’s in charge of Amazon’s global advertising expansion efforts in Canada, Australia, Latin American and beyond.

Kevin Peesker
President, Microsoft Canada

A Saskatoon native with a global resumé, Peesker has embraced the Toronto lifestyle: coaching hockey and cottaging in Muskoka. He’s about to embark on a hiring spree for Microsoft Canada, adding 500 staff over three years, investing in AI and spending half a billion to upgrade the company’s properties across Canada.


Three skyline-altering developments on the horizon

King Toronto
Mediterranean living on King Street West

The union of Allied, Westbank (led by Ian Gillespie) and starchitect Bjarke Ingels will result in four rugged peaks, evoking a Mediterranean mountain town and paying homage to Moshe Safdie’s Habitat 67. It will feature 440 units across 650,000 square feet and incorporate heritage façades at street level.

CIBC Square
The big news on Bay Street

A co-production between Hines and Nathalie Palladitcheff’s Ivanhoé Cambridge, CIBC Square will transform the financial district. Two towers, one 49 storeys, the other 50, will cover three million square feet, connect to Union and Scotiabank Arena and feature a one-acre park bridge between buildings. Tower one opens late 2020.

The One
Towering ambition at Yonge and Bloor

Sam Mizrahi is officially putting First Canadian Place on notice. Thanks to funding from a Korean real estate investment company, his The One will become the country’s tallest skyscraper, at 309 metres and 85 storeys. Floors four through 16 will become an Andaz Hotel; the ground floor will be commercial.

This story originally appeared in the December 2019 issue of Toronto Life magazine. To subscribe, for just $29.95 a year, click here.