The Influentials 2018

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

Hardly anything went down in Toronto this year that didn’t bear the new premier’s imprimatur. Recreational pot became legal, but not before Ford steamrolled the pre-existing plans and implemented a framework for private sales. In September, students and teachers returned to the classroom unsure of whether they were allowed to call it a penis or a pee-pee or anything at all. A little over a month before voters went to the polls, Ford chucked the municipal electoral process into a blender. He roadblocked Trudeau’s carbon tax scheme, cancelled the basic income pilot and went on and on about the all-curing virtues of one-dollar beer. So steady was the firehose feed of news flowing from Queen’s Park that you’d be forgiven for not paying attention to the other influential Torontonians who were busy changing the world in 2018. Chrystia Freeland emerged semi-­victorious from her NAFTA arm-wrestle with Trump; Drake conquered the music world, and then Shawn Mendes did, too; a quirky Jungian psychology professor became the guiding light of a new global men’s movement; our adopted frightmeister, Guillermo del Toro, snagged four golden statuettes on Hollywood’s biggest stage; Jessica Mulroney became Pippa 2.0; and one brave, level-headed police officer at Yonge and Finch decided to holster his gun, rather than fire it—demonstrating to a world grappling anew with racism, bigotry and violence what Toronto is truly about.

Markian Lozowchuk


1 At the beginning of 2018, the Ford family circus seemed like a distant hallucinogenic memory. By year’s end, its wiliest son was running the province with a Lannisterian will. Doug, a few notches smarter than Rob, got to work right away, recalling the legislature for a rare summer session. With unprecedented speed and ferocity, he torched several of Kathleen Wynne’s signature initiatives: the cap-and-trade carbon emissions program (as well as a related $100-million school repair fund), the sex-ed curriculum, the Ontario Basic Income Pilot. He froze salaries for public service managers and halted new measures on police oversight. And, of course, he chopped Toronto city council in half, which was, depending on your point of view, either a brilliant cost-cutting move or a puerile act of vengeance. “Promise made, promise kept,” Ford said, with hashtag regularity. In other words, burn it all down. Up next: Figuring out how to balance the provincial budget, while keeping his promise not to slash jobs or services.

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Markian Lozowchuk

Minister of Foreign Affairs

2 With America on sabbatical as global defender of human rights, Freeland has leapt into the void. In August, she called out MBS, the power-mad Saudi prince, for jailing a women’s rights activist. When he levied sanctions, kicked out Canada’s ambassador and ordered all Saudi students to leave Canada, Freeland doubled down, stating that Canada was “very comfortable with its position.” A month later, she appeared on a panel called “Taking on the Tyrant,” which featured a video montage of Trump alongside autocrats like Syria’s Bashar al-Assad and China’s Xi Jinping. The timing didn’t help her relationship with POTUS, who was growing frustrated with the stalled NAFTA talks. “We don’t like their representative very much,” he said of Freeland, who remained characteristically unfazed. For the umpteenth time in 2018, she visited Washington in pursuit of a favourable agreement for Canada. Finally, in October, she secured a deal that protects Canada’s vital industries and, rebrand aside, isn’t so different from its predecessor. Friends in high places: In April, Freeland hosted all the G7 foreign ministers for brunch at her Summerhill house.

Markian Lozowchuk


3 Call him bland or a ditherer, but he must have done something right to nab 63 per cent of the vote. Tory is a no-surprises maintenance man who worries, so we don’t have to, about all the unsexy stuff that keeps our metropolis running. To his credit, he has proved a smooth operator, pushing through overdue TTC improvements (express buses and reduced fares for people with disabilities, for two), forming committees (on important but dull stuff like construction road closures) that get things done, and avoiding major strikes and service disruptions. We also take for granted his steadiness when confronted with the previously unimaginable horrors of mass shootings and van attacks on our streets. Right now, with the sheer craziness to the south and the rule-by-spite at Queen’s Park, it’s nice to have Mister Reliable minding city hall. Up next: Funding for his SmartTrack transit plan finally won approval at council, but the entire thing could be a wash if he doesn’t get on the premier’s good side.

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4 In 1966, John Lennon said the Beatles were bigger than Jesus. In 2018, Billboard decreed Drake was bigger than the Beatles when he smashed a longstanding Fab Four record: seven of his songs appeared on the Top 10 simultaneously. Also this year, he opened the sports joint Pick 6ix, reunited the Degrassi crew for the “I’m Upset” music video, produced the police-violence film Monsters and Men, and delivered the song of the summer, “In My Feelings.” All of this matters because, outside of Canada, the first—and sometimes only—thing millions of people know about Toronto is that it’s Drake’s hometown. When he looks good, so do we. Charity circuit: He blew his “God’s Plan” video budget (roughly $1.23 million) on shopping sprees, university scholarships and other charitable causes for the people of Miami.

Daniel Ehrenworth


5 In the course of a year, Peterson went from eccentric prof to global phenomenon. His 12 Rules for Life, a self-help guide to enjoying a more enlightened existence, topped bestseller lists around the world. The New York Times columnist David Brooks called him “the most influential public intellectual in the Western world,” and by the fall, his book had sold more than two million copies. Up next: Pursuing defamation lawsuits he’s launched against two Laurier professors and a former staff member who compared him to Hitler.

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6 Atwood’s fictional worlds have never been more alive in popular culture. Alias Grace earned critical fawning and roughly four million viewers on CBC plus millions more on Netflix. Season two of The Handmaid’s Tale was as good as—if bleaker than—the first. Even if the Emmys semi-snubbed the show (20 nods but no major wins), viewers didn’t; the season two premiere attracted twice the audience of the original’s. Women in red robes and white wings popped up to protest the Kavanaugh confirmation in Washington, to rally for abortion rights in Argentina, to stage an operatic Handmaid’s Tale adaptation in Australia. Up next: Season three of The Handmaid’s Tale.

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Attorney General

7 The Harvard- and NYU-educated quadrilingual descendant of Canadian political royalty brings sophistication to an often pugnacious regime. When Ford wanted to deploy the notwithstanding clause to ram his council-slashing bill through the legislature, he tasked Mulroney with publicly defending it, then called on her again to spearhead the tricky cannabis file. Lately, she’s been touring the province and meeting with business owners who want to repeal the Liberal government’s efforts to raise the minimum wage to $15 an hour. Friends in high places: George W. Bush and Queen Noor of Jordan attended her 2000 wedding to Andrew Lapham.

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Governor of the Bank of Canada

8 Poloz decides when to lower the Bank’s overnight rate and when to raise it, an equation that affects the worth of the dollar and the interest rate Torontonians pay on our gargantuan mortgages. Over the past five years, his other decisions have lessened the blow of Alberta’s oil collapse, kept inflation on target and wrangled unemployment to a four-decade low. This year, when POTUS threw a trade temper tantrum, Poloz boldly raised the overnight rate from 1.25 to 1.5 per cent, betting Canada would thrive despite a volley of tariffs. The arrival of USMCA proved him right. Up next: Before his term ends in June 2020, he’ll have to decide what to do with the overnight rate a dozen more times.

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9 The horror-fantasy auteur’s masterpiece, The Shape of Water, earned a field-leading 13 Oscar nominations. When it won four trophies, including Best Picture and Best Director, del Toro used his acceptance speech to crusade for inclusion and immigration. His success is a boon to the Toronto film industry: del Toro has been shooting here since 1997’s Mimic, and every blockbuster he films in Ontario means more money, work and prestige for local crews and studios. Up next: In 2019, he’ll produce the Keri Russell horror flick, Antlers, direct Pinocchio for Netflix, and—the truest indicator of iconic status—make an animated cameo on The Simpsons.

Craig Boyko

Director, Art Gallery of Ontario

10 Stephan Jost kicked off 2018 with Guillermo del Toro’s Monsters exhibition, which drew 192,000 visitors. He followed it with Infinity Mirrors, a kaleidoscopic journey through a series of eye-popping rooms. That exhibit wasn’t just a success on Instagram; it was a financial boon (169,000 visitors) and confirmation that the AGO isn’t just for monocle-hoisters and art majors. It’s a cultural centre for all, an oasis of thought-provoking works, live concerts, evening yoga sessions and much more. Friends in high places: He’s on a first-name basis with the Obamas.

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Chief of Police

11 Two catastrophes—the Yonge and Finch van attack and the Danforth shooting—and a string of violent incidents made the summer of 2018 memorable for all the wrong reasons. But when Constable Ken Lam stared down Alek Minassian at Yonge and Sheppard and chose to holster, rather than fire, his sidearm, the Toronto Police—and their leader, Saunders—became a symbol of everything that’s right about law enforcement, especially in the eyes of Americans fed up with police brutality. Up next: Modernizing the force by deploying officers where and when their presence is most needed, a reform that’s long been challenged by the union.

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Pop star

12 The kinder, gentler Justin Bieber is now eclipsing his forerunner. His self-titled 2018 album shot to the top of the Billboard 200 chart and earned him Billboard’s inaugural Artist of the Year award, the same honour he picked up at the MMVAs. He’s now a certified A-lister: he graced the cover of Variety’s Young Hollywood issue, attended his first Met Ball, scored an invite to Taylor Swift’s American Music Awards after-party (with a trophy in hand), made cameos on The Voice and Ellen, landed on Justin Trudeau’s summer playlist, rocked the Jingle Ball tour with Cardi B, received an adoring write-up in the Time 100 from his hero John Mayer and performed for the Queen. Dave Grohl called Mendes a “bad motherfucker”—a compliment in Foo speak. Oh, and did we mention he’s only 20 years old? Up next: Starring in an Ivan Reitman movie musical called Summer of Love.

Erin Leydon

Leader of the official opposition

13 For the 60 per cent of voters who didn’t support Doug Ford, Andrea Horwath, the Steeltown-raised, scrapyard-tough opposition leader, is their best hope. After spending her entire Queen’s Park career in third place, Horwath returned from the political wilderness to capture nearly 2 million votes, 40 seats and official opposition status. She has put her enhanced power and elevated profile to good use. In July, she condemned Ford’s ham-fisted attempt to repeal the sex-ed curriculum, and when Ford introduced the bill to gut the size of city council, Horwath orchestrated a protest so loud and disruptive that the sergeant-at-arms had to escort her from the legislature. Friends in high places: Blues rocker Tom Wilson from Blackie and the Rodeo Kings.

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General manager and president, Toronto Maple Leafs

14 What’s more stressful than leading the Leafs when they’re terrible? Doing it when they’re good. That privilege falls to Shanahan and Dubas, his 32-year-old rookie GM, who have given a few million hockey obsessives reason to live again. This summer, with the team looking like a Stanley Cup maybe, they signed John Tavares to a gigantic seven-year, $77-million (U.S.) contract, giving the team three all-star snipers. They’re changing the organization in other ways, too: Dubas hired Hayley Wickenheiser, former captain of Team Canada, as assistant director of player development, and after instituting a “name-blind” hiring policy, brought on Noelle Needham, a former player from Minnesota State, as a scout. Up next: Flair. Dubas’s predecessor, Lou Lamoriello, was known for his cultural straitjacket approach—no beards, no flash and no interviews beyond the daily beat reporter hits—but Dubas believes that a player performs best when he can express himself. Hence, a GQ spread featuring Auston Matthews in September, and Mitch Marner rocking a camouflage suit with leopard-print shoes during the pre-season.

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Style advisor

15 When she ascended the steps of Windsor Castle for the wedding of her bosom buddy, Meghan Markle, the world took to their keyboards asking the same thing: “Who is Jessica Mulroney?” Pippa 2.0 a.k.a. the Royal BFF a.k.a. style advisor to the stars became a thing on a global scale. Today, the combo of sizable reach (260,000 Insta-followers), charmed lifestyle and high-wattage connections are catnip for advertisers who’ll happily pony up for her Midas touch, and brands like Smythe and Sentaler have benefitted hugely from her endorsements. Friends in high places: Shania Twain and Olympic skater Tessa Virtue.

Daniel Ehrenworth

Reality TV star

16 The multifaceted Matheson has emerged as the most popular name in Toronto food. He’s more famous than our most decorated chefs, better-travelled than most diamond elite frequent flyers and more lovable than, well, anyone. His two shows on Vice, Dead Set on Life and It’s Suppertime!, do big business, and the former snagged him two Canadian Screen Award nominations in March. His newest endeavour—author—is solid gold, too. Since hitting shelves in October, Matty Matheson: A Cookbook, has been named an NYT bestseller, and he’s on a global promotional tour. His rave-worthy pizza joint, Maker, just opened a second location in North Toronto. Up next: His as-yet-unnamed new restaurant opens in mid-2019, and a clothing line is in the works.

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CEO, Indigo

17 Years ago, Heather Reisman proved herself a counter-revolutionary by declaring print undead. This fall, she doubled down on that bet by taking her cultural department store concept—books plus covetable products plus chill vibes—to the U.S., with a 30,000-square-foot store at the Mall at Short Hills in New Jersey. Her “Heather’s Picks” can make an author’s career. Up next: Deciding whether to buy Barnes & Noble, the struggling American book chain. It’s got baggage, but it’s also her main competition in the U.S.


Managing Partner, Georgian Partners

18 LaFayette’s firm had made big-time investments in success stories like the takeout app Ritual, accounting software FreshBooks, education platform Top Hat and retail behemoth Shopify. This past August, Georgian raised $714 million, the largest independent VC round in Canadian history—cash that banks and other investors have entrusted to Georgian to pour into auspicious start-ups and, in turn, further propel Toronto into tech superstardom. International VCs venerate Georgian’s approach to AI and data, which is good news for the city: they’ll take LaFayette’s word on which companies are worth investing in, driving more dollars into the country. Side gigs: He sits on the board of Canada Learning Code, an educational organization that recently received $8 million as part of the federal government’s CanCode initiative.

Thomas Van Der Zaag


19 Most years, Tagaq sells out concert halls. This year, she packed libraries and bookstores. In September, the Polaris-winning throat singer published her debut novel, Split Tooth, a semi-autobiographical coming-of-age story set in 1970s Nunavut. Every bit as entrancing and carnal as Tagaq’s music, it earned a spot on the Giller long list before it hit shelves and spawned a cross-country promo tour. She’s the North’s emissary to Toronto, shaping how the city thinks about Canada’s Indigenous people by shattering musical conventions, waging Twitter wars about colonialism and unapologetically sporting seal skin. Up next: Throat, a National Film Board documentary about Tagaq, will premiere in winter 2020.

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Chairman, the Woodbridge Company

20 Press shy, socially awkward and unfathomably loaded, the 3rd Baron Thomson of Fleet proved again in 2018 that billionaires needn’t be loud to be effective. Through the family’s Woodbridge Company and his personal enterprise, Osmington, Canada’s richest man controls financial information (Thomson Reuters), media (the Globe and Mail), sports (the Winnipeg Jets), real estate (proposed megamall sites in Brampton and Barrie) and art (the world’s largest collection of works by John Constable). Thomson is also dropping roughly $125 million on a 10-storey technology centre in the Entertainment District that will employ 1,500. Up next: When the long-running facelift of Union Station wraps up, it will become as much a tourist destination as a waypoint, with open, airy and modern architecture and swishy shops and restaurants.

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Member of Parliament

21 Toronto’s former top cop graduated from narc to stoner hero when he pulled off legalization without inciting a nationwide rash of blazed tomfoolery. But by October 17, Blair was on to bigger things. As Trudeau’s minister of border security and organized crime reduction, he has a sprawling portfolio with a massive to-do list. He’s already begun consultations on handgun and assault weapons bans and conversations with Homeland Security about improving the Safe Third Country agreement. Up next: Cracking down on gang activity and curbing cross-border opioid smuggling.

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Artistic director and co-head, Toronto International Film Festival

22 With the departure of Piers Handling, Bailey retains his artistic director title but also becomes co-head alongside newcomer Joana Vicente. It’s the best of both worlds: he remains the face of the festival without assuming the administrative baggage and can instead focus on his first love: film (he took 14 scouting trips across four continents this year). The 2018 fest attracted 600,000 attendees, added $190 million to the local economy and screened 147 world premieres—including The Hate U Give, If Beale Street Could Talk and Gloria Bell—plus directorial debuts from Bradley Cooper (A Star Is Born) and Jonah Hill (Mid90s). Friends in high places: Spike Lee, Guillermo del Toro and Paul Thomas Anderson.

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President, Toronto Raptors

23 Heading into the summer, the Raps were in crisis. Absent major changes, the team was headed for another great season followed by an early playoff exit. Ujiri took action, swapping hometown star DeMar DeRozan to San Antonio for the mercurial, uber-talented Kawhi Leonard and the underrated guard Danny Green. Many fans were outraged. Drake wrote a lament for his departed Rap; Kyle Lowry avoided the press. But nothing heals wounds like winning, and the team, newly constructed, is better than ever. If the decision pans out, he deserves to be knighted. Friends in high places: Barack Obama visited his basketball camp in Kenya this past summer.

Dave Gillespie

Chef and owner, Alo

24 Some of our most famous chefs seem to spend more time sweating on Iron Chef, posting Instagram selfies and hosting European food tours than they do in their own restaurants. Kriss isn’t like that. He’s always in the kitchen at Alo, obsessing over his exquisite, seasonal set menus and the choreography of his kitchen team. He’s revered by chefs as much for the brilliance of his plates as for his ability to keep such lofty standards, three years running. His two new, more relaxed spin-offs, Aloette and Alobar, rank among our best restaurants. Friends in high places: Daniel Boulud, his mentor and former boss, often visits Kriss when he’s in town, sometimes co-hosting special collaborative lunches.



25 The funniest foursome in Canadian comedy is following the same path to global stardom blazed by Kids in the Hall, SCTV and, more recently, Nathan For You. The hit CBC show plays on IFC in the U.S., where it’s just as appreciated as another cultural export (“Baroness Von Sketch Show Is The Best Thing To Come Out Of Canada Since Ryan Gosling,” exclaimed Vogue). Their niche is richly produced, tightly edited, wickedly funny send-ups of urban living—book clubs where no one has read the book, inspirational tattoos, short-lived marriages—with a serious Toronto bent (think white squirrel cameos). In the era of #MeToo, some of their best sketches are savage takes on male power. Friends in high places: Samantha Bee is an admirer.

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Entertainment moguls

26 Civic boosterism has traditionally been Drake’s thing, but this spring, the Weeknd got in on the act. Along with his artistic director and long-time friend, La Mar Taylor (they met on the first day of high school), and marketing guru Ahmed Ismail, the Weeknd launched HXOUSE, an incubator for creative young people based out of the Artscape Daniels Launchpad on the waterfront, doing for artists what already exists for tech. Musically, the Weeknd’s hitmaking ways continued, with “My Dear Melancholy” reaching number one on the U.S. Billboard top 200. Up next: Touring the HXOUSE model to cities around the world.

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27 Atwood isn’t the only Toronto author enjoying a renaissance. In July, Ondaatje’s 1992 masterpiece, The English Patient, won the Golden Man Booker Prize, a one-off award for the best book to win the prestigious honour over the past 50 years. He was a contender for the 2018 Man Booker, too, with the long-listed Warlight, a shadowy novel about two teenagers in post-war London. The book received glowing reviews and earned a spot on Barack Obama’s summer reading list. Up next: Slumdog Millionaire writer Simon Beaufoy is adapting Ondaatje’s In the Skin of a Lion into a film.

Evaan Kheraj

Defence lawyer

28 The biggest name in Canadian law has taken on another high-profile case: Mark Norman, the former vice-admiral implicated in a thorny supply ship procurement deal that might spell trouble for Trudeau. In September, Henein, who has a predilection for smoky eyeshadow, big hair and couture everything, appeared on The Social with a forceful message about fashion and the workplace: “If you make the mistake of conflating what I look like with my capability, you’re in for a sorry lesson.” Side gigs: She found time in 2018 to go on a mini speaking tour.

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Editor-in-chief, the Toronto Star

29 When Gentle was announced as the new editor of the Star in June, the newsroom erupted in cheers. The first female editor-in-chief in the paper’s 126-year history oversees a large staff (23 report directly to her) and bears the responsibility of managing the most widely read newspaper in Ontario. Under her leadership, the paper is pushing for more hard news than ever, with a renewed focus on local. Up next: Gauging the results of the Star’s new-old paywall, an initiative that flopped the first time around.

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President, Bell Media

30 While much of traditional broadcast media retrenches, Lennox, the shot-caller at Canada’s media giant, has gone on a spending spree. He snapped up a stake in Pinewood Studios and Just for Laughs, partnered with Lionsgate to bring the premium pay TV service Starz to Canada and, when Rogers dumped Vice, scooped up the Viceland library. He also launched the BNN Bloomberg channel and welcomed Michael Bloomberg to Toronto for the festivities. Lennox was one of the primary forces behind the Martin Scorsese–directed SCTV retrospective, which will air in 2019. Friends in high places: Bono, Sting, Shawn Mendes and Kiefer Sutherland.


CEO, Penguin Random House

31 In June, when Brad Martin ceded the role of CEO to Cochrane, she became the uncontested top name in Canadian publishing. With the publication of Jordan Peterson’s 12 Rules for Life—two million copies sold and counting—she can take credit for the most commercially successful title in recent history, and award-winners Brother by David Chariandy and Bellevue Square by Michael Redhill cement her artistic cred. Up next: Publishing Michelle Obama’s memoir, Becoming.

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32 The former Temple University staffer went public with her accusations of sexual assault against Bill Cosby long before the #MeToo movement even existed. Her courage prompted 60 others to come forward, a deluge no court could ignore. Finally, this fall, 14 years after the assault, Cosby was found guilty and sentenced to up to 10 years in prison. Today, Constand works as a massage therapist and lives quietly in Toronto. Her bravery resonates. Up next: Pursuing a defamation case against former prosecutor Bruce Castor, Jr., who depicted her as a liar in a statement to the press after electing not to prosecute Cosby.

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CEO, Mattamy Homes

33 This year, Gilgan bought up an 1,100-hectare slice of Florida to build 7,800 homes, making his company, Mattamy Homes, the largest privately owned home builder in North America. In 2018, the company made $3.4 billion in revenue, and he used a tiny portion of his $3.5-billion personal fortune to buy the Four Seasons penthouse, the most expensive condo in Canada, for $31 million. Charity circuit: Gilgan raised $3.75 million for CAMH through 2018’s Tour de Bleu, an annual philanthropic bike ride from Muskoka with pals Victor Dodig and John Ruffolo.

Steven Lee

Co-founders, Chase Hospitality Group

34 Over the course of five years, the dream team of Kimel and Salm has created five superlative restaurants in the Chase, the Chase Fish and Oyster, Colette Grand Cafe, Planta and Kasa Moto. They’ve kept the streak alive with Palm Lane salad bar in Yorkville, another Planta (in Miami Beach) and Arthur’s, an American-inspired restaurant at Yonge and St. Clair. They also became the hospitality partner of Holt Renfrew. Up next: Rolling out an official franchise of the insanely popular first-person video game league, Overwatch. Kimel is the principal owner of Toronto’s franchise, which cost roughly $46 million.

Daniel Ehrenworth

Chief scientific adviser, Vector Institute

35 Toronto is to AI what the Klondike was to the gold rush. Every company that wants in on the machine-learning revolution is setting up an artificial intelligence lab here—including, this year alone, Samsung, Adobe, LG and Nvidia. Hinton is the guy to thank for that. The so-called godfather of artificial intelligence—he trained the AI aces who now work at Google, Facebook and Apple—is the raison d’être for the Vector Institute, a downtown research hub that requires its international investors to open AI labs in Canada. Side gigs: He’s professor emeritus at U of T and scientific advisor at Google Brain.


Director, Royal Ontario Museum

36 Basseches threw open the original doors to the ROM when he took over in 2016, with the refurbished eastern entrance, and free admission to the First Peoples exhibition. His hospitality has paid off. Membership has gone up 31 per cent in the past three years to 120,000. Now, he’s creating an outdoor space and performance terrace on Bloor Street, as a way of making the ROM a part of everyday public life. Up next: Launching ZUUL: Life of an Armoured Dinosaur, starring a 76-million-year-old ankylosaur that’s one of the best-preserved specimens in existence.

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37 The coolest thing out of Scarborough since the Weeknd, James made his mark in 2016 as famed sprinter Jesse Owens in Race (earning him a Canadian Screen Award for Best Actor). He followed it up with a dazzling turn in If Beale Street Could Talk and is now wowing audiences with the twisty psychological thriller Homecoming alongside Julia Roberts, who gushed about the professionalism of her young co-star on the red carpet in September. Up next: Starring alongside Chadwick Boseman in 17 Bridges, a taut drama about the hunt for a cop killer.

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38 While the debate rages on about whether King West or Yorkville is the city’s true glamour mecca, a certain nightlife swami prefers to hedge his bets. Last year, Khabouth cut the ribbon on Bisha, his lavish hotel around the corner from TIFF Bell Lightbox, the rooftop where Vanity Fair hosted their 2018 TIFF bash. This summer it was Sofia, a high-end Italian restaurant in the same building as the new Christian Louboutin flagship. The restaurant is earning raves, but for Khabouth, it’s already in the rearview. Up next: Like everyone else who wants to make their deep pockets deeper, Khabouth is getting into cannabis with his W-INK brand.

Erin Leydon

Defence lawyer

39 When cannabis was legalized this fall, half a million Canadians with simple possession charges became eligible for a legal pardon. It’s a step in the right direction, according to Enenajor, director of the Cannabis Amnesty campaign. The defence attorney, who became a named partner at Clayton Ruby’s firm at age 34, says cannabis convictions disproportionately affect racialized and Indigenous populations and can get in the way of job and rent applications, cross-border travel and custody hearings. She aims to do something about it. Friends in high places: Aurora Cannabis CEO Terry Booth donated $50,000 to the amnesty campaign.

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40 They say you can’t plan an internet outbreak, but when Drake wants his music videos to be seen millions of times over, he goes to Karena Evans. Together, in 2018, they pulled off a creative hat trick with “God’s Plan,” the insta-classic Degrassi reunion video for “I’m Upset,” and “Nice For What,” starring Rashida Jones, Issa Rae and Tracee Ellis Ross. Evans was the first woman ever to win the Prism Prize’s prestigious Lipsett Award honouring unique approaches to the craft. Friends in high places: Her mentor is Director X.

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Minister of the Environment

41 Doug Ford stormed into Queen’s Park waging war against the federal climate change plan, and Phillips, his environment minister, is his first line of offence. Phillips has held top positions at Postmedia, CivicAction and the OLG. In his new role, he’s responsible for scrapping Ontario’s cap-and-trade system, and will spend up to $30 million fighting the feds over it. If the carbon tax is a high-profile issue in the 2019 federal election, it’ll be due in part to Phillips, who’s appeared on CTV and Metro Morning to preach the anti-carbon tax gospel. Friends in high places: Postmedia CEO Paul Godfrey, TIFF’s Cameron Bailey, TD exec Tim Hockey, former mayor Mel Lastman.

Daniel Malarasi

Artistic director, Soulpepper

42 Soulpepper’s new leaf starts with artistic director Weyni Mengesha, who is moving home from L.A. to take the gig, and adding some diversity atop the Toronto theatre scene. She has directed many iconic productions (Kim’s Convenience, ’da Kink in My Hair) and won the best production Dora for last year’s Father Comes Home From the Wars (Parts 1, 2 and 3). Friends in high places: Measha Brueggergosman, d’bi.young anitafrika, Trey Anthony, Charles Officer and Ngozi Paul.

Nathan Cyprys

CEO, Decentral

43 Diiorio is Toronto’s boldest crypto tycoon. Six years ago, he went all in on Bitcoin when it cost just $9.73 apiece (today it’s at $8,379), and made off with millions. He used his earnings to help Vitalik Buterin found Bitcoin’s biggest rival, Ethereum (current market cap: $27.4 billion) and create his own company, Decentral, an incubator for blockchain projects. His latest project is Jaxx, which, with more than 1.2 million downloads, is one of the world’s most popular cryptocurrency wallets. Up next: Settling into his new home, the three-storey penthouse in the former Trump Tower, which he just bought for $28 million.

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Co-founder, Partisans

44 Josephson, the sprightly co-founder of design studio Partisans, is trying to change Toronto’s rep for architectural beigeness. His firm is behind the sublime Hearn revitalization and the delightful Hobbit hole that is Grant van Gameren’s Bar Raval. This year, Partisans co-authored the Amazon HQ2 proposal that landed Toronto a spot on Jeff Bezos’s 20-city short list, designed another stunning van Gameren restaurant called Quetzal, revitalized Ontario Place and won an American Architecture Prize for a wishbone-inspired ferry terminal proposal in Seoul. Up next: A handful of dazzling private residential commissions scattered across southern Ontario.


President, Ontario Medical Association

45 As the co-head of the grassroots organization Concerned Ontario Doctors, Alam was so effective in challenging Eric Hoskins’s attempts to rein in the health budget that leader of the Ontario Medical Association was a logical next step. She’s now the essential conduit between nearly 40,000 physicians and the health ministry, led by Christine Elliott. Up next: Trying to secure a contract for Ontario doctors. They’ve been without one for five years.

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Canada Soccer board member

46 When the biggest show on earth—the World Cup—comes to town in 2026, Torontonians can thank Bob Richardson, a board member of Canada Soccer and a major part of the team that worked on the joint bid (the U.S. and Mexico will co-host). As the person in charge of lining up government support, he got Trudeau, Wynne and Tory on the same page, and then arranged a crucial, 30-minute meeting between the PM and Gianni Infantino, the head of FIFA, at Davos. Friends in high places: Jim Watson, John Baird, Sheldon Levy and Warren Kinsella.

Daniel Ehrenworth

Founders, Wattpad

47 The brain trust behind the amateur fiction start-up had a smashing 2018, gratifying investors who’ve poured $147 million into the platform so far. The Kissing Booth, a schlocky Wattpad original, was turned into a Netflix special and peaked as the fourth most-searched title on IMDB in June. In October, Yuen and Lau, evincing a do-gooder streak, partnered with National Geographic and asked writers to submit entries on the global plastic crisis. Up next: Development of Under Glass, a novel by a Wattpad contributor named Sam Marsden. The TV and film rights were just snapped up.

Daniel Neuhaus


48 The UN climate report that’s got everyone not named Donald Trump or Doug Ford depressed—the one that says we have 20 years, give or take, before the world ends—came at the perfect time for Edward Burtynsky. Anthropocene, his exhibit at the AGO and the National Gallery, co-produced with Nicholas de Pencier and Jennifer Baichwal, is a terrifying survey of the earth’s plundered landscapes. It’s a reminder that our most skilled photographer is also a powerful political force who makes the seemingly abstract idea of environmental collapse feel urgent and all-too close to home. Up next: A European tour starting in Bologna in spring 2019.


Washington bureau chief, the Toronto Star

49 Donald Trump has always been a liar, but it didn’t much matter until he became president. Thankfully, Dale, through his indispensible Twitter feed, tirelessly fact-checks every one of Trump’s half-cocked speeches, tweets and outbursts. Dale’s 437,000 Twitter followers don’t compare to POTUS’s 55 million, but they include influential members of Congress, plus Samantha Power, Susan Rice, Chelsea Clinton and Omarosa, among many others. Journalism professor Jay Rosen, ESPN’s Keith Olbermann and NPR’s Melissa Block consider him an invaluable resource. Side gigs: In 2018, he appeared on MSNBC, CNN and PBS.


Head, Silicon Valley Bank in Canada

50 Silicon Valley Bank in Canada is a tech debt-financing firm that originated in the Valley and has lent to roughly 30,000 start-ups. It expanded to Toronto this year, and Dirks, former senior VP of network and advisor strategy at RBC, is heading it up. The firm will be a huge player in the Toronto tech scene and ensure there is enough money around for start-ups to scale and not sell before they’re ready. Side gigs: Dirks sits on the board of governors of the Royal Military College of Canada.

This story originally appeared in the December 2018 issue of Toronto Life magazine. To subscribe, for just $29.95 a year, click here.