Toronto’s 50 Most Influential: the people who changed the city in 2014

Toronto's 50 Most Influential

It’s been a big year in the corridors of power, with an infusion of ambitious new leaders in the city’s most influential institutions. Here, our annual ranking of political rainmakers, Bay Street moguls, real estate gurus, major league sports stars, celebrity chefs, culture czars, and everyone else who matters now. In a nutshell: the people whose smarts, connections and clout are changing Toronto as we know it.

Most Influential 2014: 50
Ivan Reitman, 68

Reitman got tired of not having his favourite chef near his Festival Tower condo, so he built him a restaurant. Despite its weird shrine-like quality (photos of Reitman chumming around with his famous Hollywood pals cover the walls), Montecito is a hit. That’s mostly because he let NYC chef Jonathan Waxman handle the food, which is delicious, and because of the military precision of the staff. During TIFF, the place hosted official after-parties for Robert Downey Jr.’s The Judge, and Adam Sandler and Jason Reitman’s Men, Women and Children, and welcomed many more, including Bill Murray, Robert Pattinson and Sigourney Weaver. With a Ghostbusters 3 in the making, 2015 will be another year of Reitman-related headlines. Friends in high places: Dan Aykroyd, David Cronenberg, Paul Schafer, Danny DeVito, Jennifer Garner, Kevin Costner.

Brendan Shanahan, 45
Maple Leafs

With Tim Leiweke on the way out, ­Shanahan is now the de facto ranking officer in Leafland. He was installed as team president in April and his impact was felt immediately, especially in his efforts to modernize the team from sluggish and thuggish to quick and skilled. He also introduced a Moneyball ethos to the front office by hiring a 28-year-old named Kyle Dubas as assistant general manager. Dubas relies on number-­crunching to find efficiencies, and old-school scouting. Shanahan, who was previously the NHL’s director of player discipline, has put Leafs coaching staff on a short leash. If the Leafs win, the glory will be all Shanahan’s. Up next: Integrating his new hires into the organization. His latest acquisition is Mark Hunter, an OHL general manager who’ll oversee player scouting.

Toronto's 50 Most Influential: Markus Anderson
Markus Anderson, 37
Party consultant

All paths to membership at Toronto’s Soho House, the pre-eminent meeting place for upwardly mobile hobnobbers, lead to Anderson, the long-time right hand of CEO Nick Jones. Anderson has a bloodhound’s nose for tastemakers: he crafts the guest lists for the club’s biggest international parties (including its annual Oscar bash), creates pop-up clubs during Art Basel Miami and the Berlin film festival, and has amassed a contact list that would make a paparazzo swoon. Those connections come in especially handy during TIFF: this year, Soho threw official parties for 10 films. Lately, ­Anderson has been busy starting up a new Chicago outpost, and helping open locations in L.A., Mumbai, Barcelona and Istanbul. Up next: Don’t be surprised if there’s a second Toronto Soho House in the offing.

Toronto's 50 Most Influential: Elaine Lui
Elaine Lui, 41
The Social

She’s the quirkiest, funniest and most watchable member of The Social, CTV’s answer to The View, and the active ingredient in its success. The show, now in its second season, reaches 2.4 million viewers weekly (up 300,000 from Season One) and has reeled in such high-watt guests as Katy Perry, Jessica Alba, Jane Lynch and Daniel Radcliffe. Her website, LaineyGossip, attracts 1.5 million celeb-snooping visits a month, and her general ubiquity and funky fashion sense make her a party-pages staple. Lui’s quasi-memoir, Listen to the Squawking Chicken, released in April, is mainly about her complicated relationship with her Chinese mother, whose shrill, tough-luck parenting style she credits with pushing her to succeed. It spent six weeks on the bestseller list in Canada and debuted at number one on the Globe and Mail bestseller list upon publication. Side gigs: Lainey continues to do regular hosting stints for the celebrity-gawking TV program eTalk, and in June, she was interviewed as a leading Hollywood expert for a one-hour CNN special on society’s undying fascination with celebrity news in the digital era.

Toronto's 50 Most Influential: Maureen Jensen
Maureen Jensen, 58

As executive director and CAO of the Ontario Securities Commission, she introduced rules aimed at increasing women’s representation on boards and in executive roles at publicly traded companies. The new “comply or explain” legislation requires TSX-listed firms to disclose how many women they have working in their most senior ranks, and what sorts of policies they have in place to address an imbalance. If the answers to the above are “few” or “none,” then the firm is required to explain why. The new rules came after a four-month consultation process, during which 1,000 companies were asked to complete surveys and encouraged to send written submissions. Of the 448 that responded, 57 per cent had no female directors, and 53 per cent admitted that less than 10 per cent of their senior officers were women. It’s an old (and sorry) story, but one Jensen and her colleagues at the OSC are in the process of rewriting. Up next: In response to declining revenues at boutique Bay Street firms, Jensen is trying to change the OSC’s outdated regulatory fees model, making it more responsive to a company’s economic health.

Toronto's 50 Most Influential: Jeff Melanson
Jeff Melanson, 41

Known as a turnaround king and a fierce defender of the arts, Melanson announced earlier this year that he was leaving the Banff Centre to take the reins at the Toronto Symphony Orchestra. At Banff, he was only two years into a five-year contract and had recently announced an ambitious $900-million renewal plan. There was reason to think he would pull it off: in Toronto, as head of the Royal Conservatory of Music’s Community School, he increased revenue by expanding programming and curriculum beyond the institution’s traditional roots. And later, as executive director of the National Ballet School, he doubled annual revenues to $22 million. At the TSO, he inherits a $12-million deficit and a cultural institution struggling to stay relevant. Friends in high places: Arts philanthropists Robert and Julia Foster, Alberta premier Jim Prentice, Margaret Atwood, and the McCain family (Melanson is engaged to singer Eleanor McCain).

Toronto's 50 Most Influential: Peter Gilgan
Peter Gilgan, 63
Mattamy Homes

His name is popping up across the GTA like so many new suburban homes. Gilgan recently donated $40 million to SickKids for a research centre, $30 million to St. Mike’s for a critical care tower, and $2 million to Women’s College for its ambulatory care and research wing. That’s on top of the $15 million he gave to Ryerson for its athletic centre, $10 million to build a new Oakville Hospital, $1.25 million to Sheridan College and $9 million for the Pan Am Games velodrome in Milton. In short, Gilgan, who has built more than 60,000 homes across North America, has a lot of money (his net worth is estimated at $1.7 billion), and he’s not afraid to throw it around, particularly for his pet causes: health, education and athletics. Up next: In May, Gilgan bought 3,900 hectares of land near Sarasota, Florida, for $86 million, with a view to developing it into residential communities for retiring boomers.

Toronto's 50 Most Influential: Jeff Stober
Jeff Stober, 55
The Drake

A middle-aged hotel owner may seem an unlikely arbiter of cool, but Stober’s design DNA— funky Canadiana, kaleidoscopic patterns, ironic analog technology and a healthy dose of quirk (think lawn gnomes and vintage CBC logo T-shirts)—rules the city. His Queen West hotel continues to be the neighbourhood’s anchor, and the Drake One Fifty, which opened last year in the Financial District, is the un–Bay Street restaurant of choice for suits. His empire expanded in September with the Drake Devonshire hotel, a top-to-bottom renovation of an 1880s foundry in P.E.C., and he’s in the process of opening Drake General Store outlets in HBCs across Canada. Charity circuit: He raises money for the Power Plant (he’s on the board) and regularly donates to the Parkdale Community Food Bank and Artscape.

Toronto's 50 Most Influential: Andy Byford
Andy Byford, 49

He’s head of a cash-strapped, systemically dysfunctional (and aging) transit ­operation—and responsible for the safe and timely transport of 460 million riders a year. He has handled the task with equal parts ambition and humility, promising improved customer service while personally owning up to the TTC’s failings. This year, he debuted a monthly CEO’s report, available online and delivered to city councillors, which includes a 25-point running scorecard measuring the TTC’s successes and failures. He also launched a fleet of new Spadina streetcars, computerized signals on the Yonge-University-Spadina line, and finally began rolling out the long-awaited Presto payment system, allowing customers to pay by pre-bought card, debit or credit. Up next: The level-headed CEO will push for a much-needed Downtown Relief Line.

Toronto's 50 Most Influential: Sara Diamond
Sara Diamond, 60

In many ways, Diamond is a woman ahead of her time. The president of the city’s leading art and design institution is a media arts pioneer—an artist and designer whose research is focused on data visualization and wearable technology. OCAD’s board of governors recently renewed her contract for a third five-year term, as the school continues to pivot from traditional studio-based art and design learning to the brave new world of digital technology. Undergrad enrollment in the arts was down across Ontario this fall (15 per cent at OCAD), which explains why Diamond is positioning her school as the institution at the forefront of the profitable design and tech revolution. Up next: Diamond has been expanding OCAD’s south campus, which will include a 25,000-square-foot facility (the Princess of Wales Centre for Visual Arts at OCAD University) in the Mirvish-Gehry King West development.

(Photographs: Diamond courtesy of OCAD; Byford by Markian Lozowchuk; Stober by Bryan da Silva; Gilgan courtesy of SickKids; Melanson courtesy of the Banff Centre; Jensen courtesy of OSC; Lui by Daniel Ehrenworth; Anderson by Evaan Kheraj; Shanahan by Getty Images; Reitman by Raina and Wilson)

Toronto's 50 Most Influential: John Albright
John Albright, 56
Relay Ventures

He’s the venture capital king of Toronto—one of the most active players in early-stage financing and the only one focused ­exclusively on mobile products. He’s also the Kevin Bacon of the Toronto tech scene, leveraging his deep corporate connections in Canada (BlackBerry, Thomson Reuters, Corus Entertainment, Northleaf Capital) and in the U.S. (Google, eBay, LinkedIn, Uber) to fund and advise the next generation of tech entrepreneurs. Albright has offices in Toronto and Silicon Valley, and he’s tied in with some of the best university incubators in town: Next36, Ryerson’s Digital Media Zone and OCAD’s Imagination Catalyst (in which Relay recently invested $1 million). Up next: One of Relay’s best bets is Bionym, a wearable technology developer that makes the Nymi smart bracelet—an all-in-one personal ID device that is authenticated by the user’s unique heartbeat and can replace anything requiring a PIN or a password.

Toronto's 50 Most Influential: Kevan Cowan
Kevan Cowan, 53
TMX Group

There’s nothing like competition to spur a company into action. That’s precisely what TMX Group did at the threat of the proposed (and RBC-backed) rival stock exchange, Aequitas Innovations. This year, Cowan, the TSX markets president, announced that TMX, in addition to running the Toronto, Toronto-Venture, Alpha and Montreal stock exchanges (in other words, the heart of our financial system), would launch a new service to help facilitate private investment in start-up and early-stage growth companies. TMX also released a new high-speed trading platform, Quantum XA, which has sped up trading across the TMX exchanges (trades now occur in under 0.1 milliseconds, 20 times faster than the previous speed). In August, it bought an American microwave technology network in order to increase the speed of trading between Toronto and the New York and Chicago exchanges. Up next: TMX Group will move into a new 40-storey building—the Ernst and Young Tower—at 100 Adelaide West in 2017.

Toronto's 50 Most Influential: Strombo
George Stroumboulopoulos, 42
Hockey Night in Canada

Strombo holds the second most scrutinized job in Canada, just after prime minister. Each week, more than two million hockey-crazed obsessives tune in to HNIC, a 62-year-old institution, and dissect every puck-related utterance. Strombo takes over from Ron MacLean and Don Cherry as the face of the Saturday night broadcast, lending his interview chops to longer-form features on Wednesday nights. It was a controversial pick, since he’s admired more for his musical knowledge than his sports IQ, but he got his start as a technical operator, producer, reporter and then host at The Fan. In addition to his duties, he co-hosts a weekday radio segment called “Off the Ice With Strombo and Marek” on the Rogers radio network, and he still hosts the three-hour The Strombo Show on CBC Radio 2 every Sunday night. Side gigs: Strombo emcees or hosts one or two events per week—during TIFF, it’s more like three per day—and he sits on the board of Artists for Peace and Justice, which raised $1.5 million during its annual TIFF event in 2014.

Toronto's 50 Most Influential: Fiona Crean
Fiona Crean, 61
City Hall

As the city’s first ombudsman, Crean has held the powers that be—or, in the case of Rob Ford, the power that was—to account. This year, she released her damning Toronto Community Housing report, which led to the resignation of CEO (and Ford appointee) Gene Jones. She had previously admonished Ford for interfering in the public appointments process, after he tried to stack the city’s arms-length boards with yes-men. (The hiring process is now more rigorous.) Beyond being on Ford watch, Crean’s office dealt with 1,800 complaints last year, an increase of 28 per cent from 2012. The rise in numbers might suggest that Rob Ford’s plan to improve customer service has failed. Or it might just prove the need for an ombudsman’s office in the first place. Up next: Crean’s term is set to expire in November 2015, and in July city council voted to defer the decision to renew her contract until the new year (i.e., after the municipal election).

Toronto's 50 Most Influential: Tatiana Maslany
Tatiana Maslany, 29

Orphan Black, the human cloning sci-fi hit, has gone supernova, primarily because of its versatile lead. In 2014, Maslany, who plays 10 (and counting) different roles on the show, won nine acting trophies, including the Canadian Screen Award and the Critics’ Choice Television Award, and was nominated for a Golden Globe and People’s Choice Award. The show was renewed for a third season in July. In May, she guest-starred in an SNL digital short with Pharrell and the Lonely Island, and next year she returns to the big screen, as the younger version of Helen Mirren’s character in The Woman in Gold, alongside Ryan Reynolds and Katie Holmes. Fandemonium: At Comic-Con 2014 in San Diego, Maslany walked onto the stage to a standing ovation. Before she left, more than a dozen security guards had to hold back hysterical admirers to keep them from swarming her.

Toronto's 50 Most Influential: Meric Gertler
Meric Gertler, 58
University of Toronto

The new president of Canada’s largest university is a renowned expert in the field of urban economics: he knows how critical innovation is in determining a city’s success (and, by extension, how critical U of T’s success is to its home city). He presides over 83,000 students, nearly 19,000 faculty and staff, a $2-billion ­budget and a campus that stretches from ­Scarborough to Mississauga. At a time when universities everywhere are under pressure to rebrand, specialize or otherwise differentiate themselves, Gertler is looking beyond U of T’s confines—­increasing public-private research partner­ships for the prestigious University Health Network, or solving transportation issues for commuting university students, among other things—with a view to strengthening the city itself. Up next: In September, Gertler announced a proposal (backed by Isadore and ­Rosalie Sharp) to replace the dormant ­McLaughlin Planetarium with a cultural complex that would house a Jewish museum, a concert hall and several university departments, including the Institute for Islamic Studies.

Toronto's 50 Most Influential: Karen Kain
Karen Kain, 63
National Ballet of Canada

When Canada’s prima ballerina took over as artistic director of the National Ballet in 2005, it had an accumulated deficit of $1.14 million. She quickly turned the red to black, and it’s been financially stable ever since. But to Kain, the box office and fundraising success was secondary to the more important goal of putting the country’s premier ballet company centre stage. She took risks, investing $1 million in a co-production of Alice’s Adventures in Wonderland (with London’s Royal Ballet), and creating the NBC’s own rendition of Romeo and Juliet (by the celebrated choreog­rapher Alexei Ratmansky). The company has since toured Alice to L.A., Washington and New York’s Lincoln Center—the first time the National Ballet had performed there in nearly a decade, and where it will return for an encore next spring. Romeo and Juliet played to critical acclaim in London and L.A. The NBC is back among the world’s finest companies—namely the Royal and the Bolshoi—just as it was while Kain, the dancer, was still on pointe. Global appeal: In October, the National Ballet was one of five companies to take part in the inaugural World Ballet Day, a live webcast that travelled from Melbourne to San Francisco (with stops in Moscow and London), providing real-time broadcasts of dancers at work.

Toronto's 50 Most Influential: Heather Conway
Heather Conway, 52

She has the unenviable job of trying to turn around the CBC during the most fraught time in its history. Only a year into her role, she’s already fired 657 employees, with 1,000 more expected to go over the next five years. This is in response to severe government cutbacks, dwindling ad revenues and the loss of the NHL broadcast rights to Rogers. Beyond the cuts, Conway is redoubling the CBC’s push into digital and mobile content (she says she’s inspired by the success of rebel media outfit Vice), while outsourcing most of its non-news production. This created a backlash from such veteran CBC personalities as Peter Mansbridge, Linden McIntyre and David Suzuki, who all signed a letter urging Conway to save the broadcaster’s respected in-house documentary division by rolling it in with news and current affairs. The shrewd and analytical Conway didn’t budge. In October, she fired the popular radio host Jian Ghomeshi, who is embroiled in a lurid sex scandal. Now she must contend with Ghomeshi’s upset fans and a $55-million lawsuit. Power couple: Her long-time partner is the celebrated Canadian filmmaker Patricia Rozema.

Toronto's 50 Most Influential: Charles Khabouth
Charles Khabouth, 53
Ink Entertainment

Over the course of his 30-year career, Khabouth has been at the vanguard of the city’s entertainment scene, nurturing a nascent EDM culture into adolescence (at Uniun and The Guvernment); ushering in bottle service and VIP lounges (at This Is London and Cube); and, implausibly, building a South Beach–style watering hole at the docks (Cabana Pool Bar). In August, he forged a partnership with Oliver and Bonacini to run the food and beverage operations at the Trump Tower, quickly transforming its stuffy 31st-floor restaurant, Stock, into the much swankier supper club America—just in time for it to become a hot spot during TIFF. The hotel’s main-floor bar, The Calvin, brings the Khabouth party to Bay Street. Up next: Bisha, his long-promised 41-storey condo–boutique hotel project, is finally rising on Blue Jays Way.

Toronto's 50 Most Influential: Matt Galloway
Matt Galloway, 44

He’s been a voice of reason in a time of madness and a bridge builder in a time of divisiveness. He puts the lie to the stereotype of the bike-riding, latte-sipping downtowner who knows nothing about the suburbs, because he is a bike-riding, latte-sipping downtowner and knows the burbs intimately. In his four years as host of Metro Morning—the top-rated morning show in the city, with 750,000 weekly listeners—Galloway has made diversity his mantra, drawing stories from every pocket of the city. He’s also the go-to interviewer for politicos (of each stripe), who see his show as the best way to deliver their message even if it means enduring his deceptively courteous style of grilling. Side gigs: ­Galloway is one of the most in-demand moderator-hosts in the city, regularly appearing at events at Harbourfront Centre and the Toronto Public Library, as well as mayoral debates and charity fundraisers.

(Photographs: Galloway via Wikimedia Commons; Khabouth courtesy of Ink; Conway courtesy of CBC; Kain by Aleksandar Antonijevic; Gertler by Getty Images; Maslany courtesy of Bell Media; Crean by Markian Lozowchuk; Stroumboulopoulos, Cowan by Getty Images; Albright courtesy of John Albright)

Toronto's 50 Most Influential: Masai Ujiri
Masai Ujiri, 44

His “Fuck Brooklyn” rallying cry might have seemed off the cuff, but it was a highly calculated gambit aimed at boosting the pride of his team and fan base. Ujiri can evince a more measured side, too: in August, when Atlanta Hawks GM Danny Ferry made racist comments about African players, Ujiri wrote a poignant op-ed in the Globe and Mail damning the message while still respecting Ferry’s character. His biggest coup, however, was leading the Raptors to their winningest season in franchise history, making the playoffs for the first time since 2008. In the off season, he re-signed the coveted Kyle Lowry. He’s got his core players back for 2015, and expectations are high—maybe impossibly so. Charity circuit: In June, he hosted a benefit dinner for the Nelson Mandela Foundation, and reeled in Wolf Blitzer, Danny Glover and various NBA stars, raising $300,000.

Toronto's 50 Most Influential: David Walmsey
David Walmsley, 44
The Globe and Mail

It’s fitting that Walmsley’s Twitter bio is just one word: Newsman. The British-born editor-in-chief of the Globe and Mail is markedly different from Globe editors past: a charming and low-key leader with a passion for traditional news reporting. Walmsley spent six years at the paper (from 2006 to 2012) and was the number-two to former editor John Stackhouse, whose pedantic approach to journalism reportedly didn’t jibe with Walmsley’s Fleet Street roots. He left to head up news content at the CBC, before being wooed back earlier this year with an offer of the Globe’s top job. Since then, he’s been on a hiring spree, scooping up top reporters from his competitors (most notably Robyn Doolittle and Cathal Kelly from the Toronto Star) while steering the Globe away from such high-minded content as “Our Time to Lead” and toward something a little more, well, newsworthy. Claim to fame: Rob Ford entered rehab shortly after Walmsley ran photos of the mayor holding what appeared to be a crack pipe.

Toronto's 50 Most Influential: Ian Nordheimer
Ian Nordheimer, 63
Ontario Superior Court

He’s the most famous judge in Ontario’s higher court. In his 10 years on the bench, he’s presided over the investigation into Royal Group Technologies, which briefly implicated then–finance minister Greg Sorbara (who was eventually cleared); the Jane Creba, Glen Davis and Stefanie ­Rengel murder trials; Brian Dickson’s “webcam murder” trial; and the guns and gangs investigation known as Project Traveller and its spinoff Project Brazen 2. In the case of Brazen 2, the lawyers for Sandro Lisi had argued for a ban on the publication of information obtained under search warrant, which Nordheimer rejected. He believes public access to court information trumps the risk that it might affect the defendant’s right to a fair trial. Ripple effect: Nordheimer’s “right to know” decision was recently cited by the commissioner of the Elliot Lake mall inquiry, after lawyers for the lone accused, engineer Robert Wood, asked that parts of the inquiry report be censored.

Toronto's 50 Most Influential: Bharat Masrani
Bharat Masrani, 58

Masrani takes over at Canada’s second-largest bank (by market cap) at an auspicious time. TD’s balance sheet has never been better: its second quarter profits were $2.1 billion, 37 per cent higher than the previous year. Its U.S. expansion—which accounts for approximately 35 per cent of the bank’s adjusted gross income—is beginning to show promise, with a steady increase in profits. And for the first time ever, TD is challenging RBC’s hegemony as the bank with the most assets. While out­going CEO Ed Clark deserves much of the credit, Masrani has been at his side for the last 12 years, plotting, strategizing, building. Together, they decided to eliminate TD’s exposure to toxic ­mortgage-backed securities ahead of the 2008 financial crisis. And together they planned the bank’s multibillion-dollar U.S. invasion, which Masrani oversaw. Global appeal: Masrani has lived all over the world, including Uganda, England, Canada and the U.S.

Toronto's 50 Most Influential: Katie Taylor
Katie Taylor, 56

In her bid to succeed former RBC chair David O’Brien, Taylor was up against some stiff competition—namely Geoff Beattie, a fellow long-time board member and Bay Street golden boy who also happens to be besties with the bank’s CEO, Gord Nixon. In the end, Taylor prevailed, becoming the most powerful chair in the Canadian financial universe. RBC is one of the country’s largest banks (neck-and-neck with TD), and Taylor has been on its board for the past 13 years, working on its audit, risk and human resources committees. On her watch, the number of women on the board has risen to 33 per cent. She was an avid supporter and participant in the OSC’s review of its proposed “comply or explain” rules, and speaks regularly on the importance of diversity in the workplace. Side gigs: Taylor is a director of the CPPIB, chair of the board of the SickKids foundation, and an advisor to both McGill and the Schulich School of Business.

Toronto's 50 Most Influential: Jorn Weisbrodt
Jorn Weisbrodt, 41

With Weisbrodt at the helm, the city’s largest arts extravaganza keeps getting better. For this year’s festival, he again leveraged his extensive global network—he reportedly has 8,000 contacts programmed into his phone—to bring such big-name artists as Matthew Barney, David Byrne, Josh Groban, The Roots, Bebel Gilberto and Ziggy Marley to town. At the same time, he wisely drew on Toronto’s homegrown talent, enlisting the participation of the TSO, the Hidden Cameras and Jason Collett, among many others. He even hired the Parkdale restaurant Parts and Labour to provide catering for Luminato’s newly licensed hub at David Pecaut Square. Bragging rights: Luminato contributes roughly $60 million a year to the provincial economy, a factor in the Wynne government’s decision to extend its funding ($2.5 million annually) for another three years.

Toronto's 50 Most Influential: Robert Deluce
Robert Deluce, 64
Porter Airlines

The most divisive man in Toronto not named Ford has waged an unrepentant crusade to bring jets to the Island airport. The Toronto Port Authority is shelling out $3 million on a feasibility study ­analyzing runway designs and environmental impacts, which they’ll present to council next year. Deluce, meanwhile, is racking up PR points. In May, CVCA, Canada’s Venture Capital and Private Equity Association, named him entrepreneur of the year, and in July, Skytrax dubbed Porter North America’s best regional airline. In early 2015, the pedestrian tunnel from the foot of Bathurst to the island will open, allowing passengers to access the airport without enduring that absurd 20-second ferry ride. Not all developments are rosy: Porter is considering selling its terminal (estimated value, $500 million), a sign the company is hard up for cash. With financial pressures and a make-or-break verdict on jets, the year ahead will be the toughest of Deluce’s career. Friends in high places: Paul Godfrey, Brian Burke, Doug Gilmour, Richard Ivy.

Toronto's 50 Most Influential: Naomi Klein
Naomi Klein, 44

Fifteen years after her debut book, No Logo, propelled her to international fame and made her the chief spokesperson for the anti-globalization movement, Klein is back with a scathing indictment of big oil. In This Changes Everything, she documents capitalism’s destructive war on the environment through a combination of on-the-ground reporting and economic and political analysis, all of which hits very close to home. It’s as though the book is addressed to the pro–oil sands Stephen Harper himself—when Klein won the $60,000 Hilary Weston Writers’ Trust Prize for Non-fiction in October, she sarcastically thanked the prime minister for the book’s success. Every time she speaks or tweets, thousands of people organize (she has 240,000 Twitter followers). Every time her writing appears in Harper’s, The Nation, Rolling Stone or The Guardian, debate ensues. And every time she writes a book, a new global movement is born. Friends in high places: Acclaimed film directors Alfonso Cuarón and Michael ­Winterbottom, Nobel Prize–winning economist Joseph Stiglitz, celebrity chef René Redzepi, designer Vivienne Westwood.

Toronto's 50 Most Influential: Heather Reisman
Heather Reisman, 66

The past year saw Reisman’s transformation from book mogul to budding ­Hollywood power player. She produced Fed Up, the Katie Couric–narrated doc about the evils of Big Sugar, and followed her and husband Gerry Schwartz’s $5-­million donation to the Academy Museum of Motion Pictures with a ­$2-million cheque to TIFF to support film preservation, filmmakers and exhibitions. A rebranding is happening on the corporate front, too: at Indigo, the evolution from bookstore to what she calls the “world’s first cultural department store” has been a success: general merchandise now comprises 27 per cent of all revenue. For the first quarter of 2014, the company’s revenue was $181 million, up 5.4 per cent from a year previous (the opposite trajectory of American book retailers). Part-time gigs: She’s a member of the Bilderberg Steering Committee and recently joined an eight-person panel headed by ex–U of T president David Naylor to advise the federal government on ways to improve Canada’s health-care system.

Toronto's 50 Most Influential: Saad Rafi
Saäd Rafi, 54
Pan Am Games

At Queen’s Park, Rafi was known as the anti-bureaucrat—a tech- and systems-minded administrator who knew how to get stuff done. He cut an imposing swath through the legislature, as a heavyweight deputy minister who worked well under both the Conservatives (Harris and Eves) and the Liberals (McGuinty and Wynne). In his role as head of the Pan Am Games, he’s in charge of a $1.44-billion budget, about 400 employees (700 come Games time), 32 venues and some 23,000 volunteers. He’s also responsible for ensuring the Games go smoothly for the 6,000 athletes who are expected to travel here from 41 countries. In some ways, his new job was made for him: his government portfolios included economic development and trade, transportation, health, and energy and infrastructure (between 2005 and 2008, he worked as an infrastructure advisor at Deloitte), all of which will serve him well as he tries to get the wayward Games back on track. Oh yeah, and he did a stint as deputy community safety minister in 2003, the year of both the blackout and SARS. There are so many things that could go wrong with the Pan Ams, a little disaster preparedness can’t hurt. Friends in high places: Kathleen Wynne, Deb Matthews, David Peterson.

(Photographs: Rafi courtesy of Pan Am Games; Reisman by Daniel Ehrenworth; Klein by Kourosh Keshiri; Deluce by Getty Images; Weisbrodt courtesy of Luminato; Taylor by Markian Lozowchuk; Masrani courtesy of TD; Walmsley courtesy of CJF; Ujiri by Jon Bielaski/Light Imaging)

Toronto's 50 Most Influential: David Mirvish
David Mirvish, 70
Mirvish Productions

You have to admire a guy who inherits a family business that’s linked to the cultural heritage of the city, then—legacy be damned—rejects said heritage in the name of modernism and reinvention. Mirvish has not rested on the laurels of his father. Instead he chose to tear down the King West blocks known as Theatre Row and replace them with a Frank Gehry–designed monument to the future. After butting heads with the city’s chief planner, ­Jennifer Keesmaat, over the size of the development, Mirvish had an epiphany and remembered his artistic roots. His new proposal features two towers instead of three, includes a gallery for his collection of modern art, and preserves one of his father’s warehouses and the Princess of Wales Theatre. Up next: This theatre season is Mirvish’s biggest ever, with 19 shows scheduled, including Noel Coward’s Blithe Spirit, starring Angela Lansbury.

Toronto's 50 Most Influential: Larry Tanenbaum
Larry Tanenbaum, 68
MLSE and Kilmer Group

He lost out on the Buffalo Bills, saw Tim Leiweke head for the door, and suffered the humiliation of ESPN ranking the Leafs dead last of 122 professional sports franchises in North America. And despite those knocks, Tanenbaum remains the most influential name in Toronto sports, holding the balance of power at MLSE when it comes to any decision, big or small, affecting the Leafs, Raptors, TFC or ­Marlies. He’s a quiet, behind-the-scenes type whose imprint on the city is growing (beyond the realm of sports) via his investment in the new waterfront. His company, Kilmer, is building several projects in the West Don Lands. Up next: Finding and hiring Leiweke 2.0; getting the Leafs into the playoffs and repairing MLSE’s reputation as a profit-obsessed organization incapable of wins.

Toronto's 50 Most Influential: Charles Sousa
Charles Sousa, 56
Queen’s Park

Four years ago, Sousa was a junior minister in Dalton McGuinty’s cabinet—a relative unknown. During the Liberal leadership contest in early 2013, he was in fifth place when he made the shrewd decision to withdraw and throw his support behind Kathleen Wynne. When she became leader, Wynne rewarded him by making him finance minister. After winning her ­majority in June, however, she owed no such favours, and her reappointment of Sousa illustrates her confidence in his ability to implement her daunting financial plans. Today, as the minister in charge of the province’s $130-billion ­budget, he’s the third most powerful person in the Ontario government, behind Wynne and her deputy, Deb Matthews. Claim to fame: As the MPP for Mississauga South, Sousa was a vocal opponent of the gas plant being built in his riding. He helped convince Dalton McGuinty to relocate it to Sarnia.

Toronto's 50 Most Influential: Barbara Williams
Barbara Williams, 55
Shaw Media

In September, Williams became the most powerful woman in Canadian broadcasting when she was named president of Shaw Media. Seven years ago, she was in charge of lifestyle programming at ­Alliance Atlantis before it was purchased by ­Canwest, only to see the overstretched owners (the Asper family) put it into bankruptcy protection two years later. When Shaw scooped up Canwest’s TV assets in 2010, Williams was made senior VP of content, overseeing Global TV and 19 specialty channels. She was instrumental in turning the company around, wooing Canadian producers and networks south of the border (Shaw commissioned popular dramas like Lost Girl and Rookie Blue—a co-production with ABC—and partnered with American specialty channels). As a result, the company is challenging frontrunner CTV in the all-important ratings race, and Williams is now the final arbiter of what millions of Canadians will watch when they turn on the tube. Side gigs: The media mogul is also chair of the Banff World Media Festival, ­Canada’s Walk of Fame and the Canadian Film Centre.

Toronto's 50 Most Influential: Peter Pisters
Peter Pisters, 54

Pisters is a renowned surgical oncologist who has worked at two of the leading cancer centres in the U.S.—Memorial Sloan-Kettering and MD Anderson. He’s an expert in, among other cancers, soft-tissue sarcomas like the liposarcoma afflicting Rob Ford. He received his medical degree from Western (which is where he met his wife, Katherine, a hematologist-oncologist). In January, he’ll assume the most powerful position in Toronto health-care, overseeing four teaching hospitals—Toronto General, Toronto Western, Princess Margaret and Toronto Rehab—with a staff of 20,000 (including many of the world’s leading scientists) and a total annual budget of more than $2 billion. Up next: He’ll likely be in constant contact with deputy health minister Robert Bell, his predecessor at UHN, about the city’s Ebola preparedness.

Toronto's 50 Most Influential: Joe Mimran
Joe Mimran, 62
Joe Fresh

The man behind such iconic brands as Alfred Sung and Club Monaco has managed to retain his stylistic credibility while conquering the increasingly crowded discount fashion market. Joe Fresh, his partnership with Loblaw, is an international success story, with 330 stores in Canada, six in New York (including its Fifth Avenue flagship and a recently opened stand-alone in SoHo) and over 650 in J. C. Penney locations. And this year he partnered with retail giants in Saudi Arabia, the United Arab ­Emirates and South Korea to roll out an additional 141 stores in 23 countries—­including Spain, the United Arab Emirates, Jordan, Morocco and Azerbaijan—by 2019. To date, Joe Fresh has opened three stores in Saudi and six in South Korea. Side gig: Mimran continues to promote local designers in his role as chair of the ­Fashion Design Council of Canada, the organization behind Toronto’s fashion week.

Toronto's 50 Most Influential: Michael Wekerle
Michael Wekerle, 51
Difference Capital

After a somewhat bumpy start—a few less-than-stellar investments, cutting ties with one of his co-founders and his CEO—Wek’s metamorphosis from the city’s top ­institutional trader to tech fund manager is nearly complete. Drawing on his own substantial fortune as well as support from a loyal network of big-name investors, he has built a company with $185 ­million in assets. This fall, he made a successful leap into television, replacing Kevin O’Leary on CBC’s Dragons’ Den. He’s using his newfound celebrity to promote a Toronto-Waterloo tech corridor, which he sees as key to making the Toronto region a leading industry hub. He’s buying up real estate in Waterloo, part of a 10-year plan to build what he’s calling the Waterloo Innovation Network. His vision? Converting five hectares near the university (including seven buildings and 360,000 square feet of commercial space) into a live-work high-tech community of offices, shops and condos. The plan will likely be accelerated by the launch of a new local LRT system and upgraded GO train service between Toronto and Waterloo, expected in a ­couple of years. Friends in high places: Mark Wahlberg, Ned Goodman, Frank Giustra, Jim Shaw, Gene McBurney, Conrad Black.

Toronto's 50 Most Influential: John Ruffolo
John Ruffolo, 48
OMERS Ventures

He’s been hailed as something of a ­messiah, not only for Canada’s struggling venture capital industry, but for the innovation economy writ large. The former accountant and management consultant spent more than 23 years at Deloitte, where he advised entrepreneurs and venture capitalists in the tech sector. Between 2005 and 2010, Ruffolo grew so frustrated by the lack of capital investment in Canadian start-ups that he began shaming the big financial institutions, as well as the provincial and federal governments, for their stinginess and lack of vision. Finally, one of his targets, the OMERS pension fund, said, if you’re so smart, why don’t you come on board and fix the funding problem? ­Ruffolo joined OMERS in 2011 and set up a unique in-house venture arm, which, in its three years of operation, has invested $250 million in 22 start-ups—including tech darlings Shopify, Desire2Learn, Wattpad and Hootsuite—which his team also advises. His goal is to turn Canada into a nation of innovators. Up next: Ruffolo, along with the Ontario Centres of Excellence and Ryerson ­University, co-founded Oneeleven, a business accelerator helping established Toronto-area entrepreneurs capitalize on the fast-growing, multibillion-dollar field of data-driven technology.

Toronto's 50 Most Influential: Deb Matthews
Deb Matthews, 61
Queen’s Park

The MPP from London has been at Queen’s Park for 11 years. Five of those were spent running the $50-billion health ministry, where she managed to rein in the province’s ballooning health care costs. She negotiated hard with pharmacists and doctors, forced hospitals to find innovative ways to do more with less, and introduced integrated case management for marginalized patients in need of social services. It’s because of these achievements, as well as a close friendship with the premier, that Matthews was trusted with the most important job in Wynne’s cabinet: president of the treasury board (not to mention deputy premier). As cabinet ministers in the McGuinty government, Wynne and Matthews used to go out for dinner ­regularly and are said to be uncommonly in sync. For Wynne, she’s the one to trust with the task of eliminating a $12.5-billion deficit in just three years—without alienating the coalition of centre-left voters who gave her a majority. Up next: Negotiating another pay freeze with teachers’ unions now that their 2012 contract has expired.

Toronto's 50 Most Influential: Galen Weston Jr.
Galen Weston Jr., 41
Loblaw Companies

We never thought the folksy charm that once characterized the Loblaws brand—as embodied in former spokesman Dave Nichol—could be replicated in the ­billionaire heir to the family business. G2 proved us wrong. He’s humble, he’s charming, he has a sharp business mind, and he recently consolidated his power, adding president to his existing title of executive chairman. This year, Weston expanded his family’s already substantial empire by bringing Shoppers Drug Mart into the fold—a $12.4-billion acquisition that will boost their dominance in urban markets. Shoppers has more than 120 stores in Toronto alone, and it’s a key weapon in Weston’s mission to combat the Walmart invasion by turning Loblaws into a convenient lifestyle brand. It’s a risk for the head of a major company to put himself directly in front of customers—to become the face of the brand—but Weston’s gamble is paying off. Charity circuit: The Weston family continues to be a major philanthropic force in the city. This year, they donated $50 ­million to create the Weston Brain Institute, an agency that doles out grants for cutting-edge research into dementia and ­Alzheimer’s disease.

(Photographs: Weston, Wekerle, Mimran by Getty Images; Matthews courtesy of Deb Matthews; Ruffolo by Reuters; Pisters courtesy of UHN; Williams courtesy of Shaw Media; Sousa courtesy of Charles Sousa; Tanenbaum by Reuters; Mirvish courtesy of Mirvish)

Toronto's 50 Most Influential: Mark Wiseman
Mark Wiseman, 44
CPP Investment Board

Wiseman is the man in charge of investing $5.7 billion of Canadians’ 2013 ­contributions to the Canadian Pension Plan. He has built the country’s largest pension fund into a global juggernaut, with assets valued at a staggering $219 billion (up 16.5 per cent from 2013). He’s known for his enormous brain and a carefully considered, long-term investment strategy, which is why many of the 100-plus deals he’s done over the last year were concentrated in speedily growing markets like China, India and Brazil (CPPIB opened an office in São Paolo in February). He’s especially focused on infrastructure and real estate acquisitions, and recently invested $279 million in China’s largest residential development company. Friends in high places: He organizes an annual ski trip with his former bosses and mentors, Jim Leech, who recently retired from Teachers, and Brent ­Belzberg, the founder of private equity firm TorQuest Partners.

Toronto's 50 Most Influential: Jennifer Keesmaat
Jennifer Keesmaat, 44
City Hall

In only two years on the job as chief planner, she modernized her department, producing slick online communications (including her blog, hosted roundtables on TV and Twitter, and, for the first time ever, released an annual report. Her goal is twofold: make urban planning more transparent and engage communities in the process. After more than 60 consultations with various stakeholders, she got unanimous approval for her Eglinton Connects plan—a completely redesigned streetscape (following completion of the new LRT) stretching 19 kilometres from ­Kennedy to Weston Road. She also introduced Gold Star 2.0, an initiative to expedite the approvals process for commercial development. The result? Her department approved three 60-storey office towers in less than six months. Perhaps most importantly, she’s created a new transit-planning unit within her department (there wasn’t one!) to ensure clarity and co-operation between the city and Metrolinx. It’s a critical step toward putting transit issues where they belong—in the hands of planners. Bragging rights: Her thoughtful opposition to the ambitious David Mirvish–Frank Gehry King West mega-development resulted in a scaled-back, culture-focused proposal, which was approved by council this summer.

Toronto's 50 Most Influential: David Thomson
David Thomson, 47

The ultra-private businessman (and second richest guy in the country after the B.C. magnate James Pattison) runs his family’s holding company, which owns a 55 per cent stake in the $12.6-billion media and financial data giant Thomson Reuters. In the last two years, he’s managed to turn the company’s fortunes around, partly by encouraging his 58,000 employees to focus on sales and innovation. The biggest changes are happening on the data front, where Thomson continues to duke it out with Bloomberg for world domination. Thomson, with its size and scale, is perfectly positioned to mine massive troves of financial information and carve it up in infinite (and ever more profitable) ways. Side gigs: He also owns Osmington, a going concern in the commercial real estate business and part of the Union Station redevelopment, where it will oversee concourse-level retail.

Toronto's 50 Most Influential: Cameron Bailey
Cameron Bailey, 51

It’s hard to believe, given the Year of the Fords, but TIFF is still Toronto’s biggest newsmaker, accounting for 30 per cent of the city’s global profile (measured by headlines) and 22 per cent of its prominent coverage. The festival generates $189 million in economic activity for Toronto, up about 16 per cent from 2008–2009. Bailey decided to flex that muscle by ruling that all TIFF opening weekend movies must be North American premieres. The results were mixed—some saw it as unnecessarily aggressive—but it demonstrated a certain swagger, too. He has fun: his decision to declare the first Friday of this year’s fest Bill Murray Day was both weird and inspired, and once again, Bailey showed an eye for spotting the next Academy Award contender, with Imitation Game, Foxcatcher and Wild all generating Oscar buzz. Friends in high places: Martin Scorsese, Bill Murray, David Cronenberg, Sandra Oh.

Toronto's 50 Most Influential: Drake
Drake, 28

Toronto’s mononymous rapper is bigger than ever. His net worth increased $5 million to $40 million on the strength of his record label, OVO Sound, and his album Nothing Was the Same, which debuted at number one in the U.S. and Canada, sold 1.6 million copies, was nominated for two Grammys, and won the Juno for rap recording of the year. This year’s sold-out OVO Fest was brasher and more boisterous than ever. He won raves for his adept hosting of the ESPYs and SNL (his ­impression of pot king–comedian Katt Williams was a work of art). As MLSE’s global ambassador, he’s an invaluable recruiter—he called TFC star Jermain Defoe and convinced him to sign here. He’s also a big reason why Toronto’s no longer a backwater in the minds of NBA stars like Kyle Lowry, who re-signed with the Raptors for four years. The only place Drake is more popular than IRL is online, where he’s a virtual meme factory (book an afternoon and Google “Drake Starbuck Hands,” “Old Drake,” “Drake Lean” and “Wheelchair Jimmy”). Drake wisely embraced the web mockery, retweeting and applauding the funniest jabs. He employed the love-the-haters tactic again after getting lambasted for his lint-rolling antics by distributing 1,200 OVO-branded lint rollers to Raptors fans; one later sold on Craigslist for $55,100. Friends in high places: Jay Z, Lil Wayne, Kanye West, Masai Ujiri, Kevin Durant, Tim Leiweke.

Toronto's 50 Most Influential: Donna Quan
Donna Quan, 56

As director of education, Quan presides over the fourth largest school board in North America, responsible for the educations of more than 275,000 students. She is the chief administrator of a $3-billion budget, through which she operates more than 600 schools employing nearly 40,000 full- and part-time staff. Most notably, she has been a steady hand at the tiller during a particularly stormy period in the board’s history, with plagiarism and expense scandals, tension and infighting between trustees and directors, labour unrest, and, most recently, a spate of violence on TDSB property. In response to a call for metal detectors in high schools after the recent fatal stabbing of a student in Etobicoke, Quan rightly defended the board’s safety record and stated, “We don’t want to create fortresses.” Up next: Quan has an ambitious plan to raise her students’ EQAO results 10 per cent by 2017.

Toronto's 50 Most Influential: Guy Laurence
Guy Laurence, 53
Rogers Communications

It’s been an eventful year since Laurence took over the $34-billion company. In January, only a month into the job, he oversaw Rogers’ $3.3-billion bid for new spectrum, scooping up more than 22 per cent of the available licences. ­Laurence claims the purchase was necessary to support and enhance his other big gamble: the $435 million a year Rogers is spending to be the exclusive broadcaster of the NHL. This ambitious new venture was launched along with the new hockey season, and on opening night—a matchup between the Leafs and the ­Canadiens—viewers got a taste of what’s to come: slick new studios, cutting-edge camera technology, NHL celebs and, yes, a relentless onslaught of Rogers branding. The company has its mojo back, but Laurence’s real test will be whether he can fix the customer service. Up next: Turning Rogers’ headquarters into an office of the future by instituting the same “hotelling” principle—in which employees check in and out of work ­stations—he implemented at Vodafone U.K.

Toronto's 50 Most Influential: George Cope
George Cope, 52
BCE and Bell Canada

In corporate Toronto, George Cope is the city’s alpha male. In early 2013, Cope sacked Leafs GM Brian Burke, no slouch in the ego department himself, because he found him crass. Now Tim Leiweke is on his way out the door, leading many to speculate that he, too, ran afoul of Cope. Bell may have lost the NHL rights to their archrivals at Rogers, but they’ve got just about everything else, including the Super Bowl, Academy Awards and Golden Globes. In September, Cope signed a multi-year deal with HBO to upgrade the offerings of TMN, making past seasons of Game of Thrones, Girls, Sopranos, Boardwalk Empire and True Detective available to subscribers on demand (and nowhere on Netflix Canada). Shareholders are clearly pleased: in the last five years, BCE’s stock value has increased by 23 per cent. Master plan: Bell gave $5 million to ­Canadian social media startup Hubub, betting that it’ll become the online home base for fans of Bell’s various TV properties.

Toronto's 50 Most Influential: Kathleen Wynne
Kathleen Wynne, 61
Queen’s Park

She’s the first premier in 20 years to be unapologetically, unabashedly pro-Toronto, and she’s a talented politician whose personality—marked by candour—has won the respect of colleagues at both ends of the political spectrum. Her personal brand is also the reason Ontario voters surprised her with a majority government in the June election. She has already set some bold policies in motion, promising to tackle the looming retirement crisis by creating the first provincial pension plan, and investing heavily in transit, in part by diverting more than $1.2 billion a year in gas taxes. But perhaps the best evidence of Wynne’s substantial influence on the city was in the unusual tenor of the mayoral campaign. For years, candidates have typically run against Queen’s Park—demanding more money or power or the uploading of services. This year, however, John Tory (who once lost to Wynne in Don Valley West), Doug Ford (her ideological opposite) and Olivia Chow (a New ­Democrat) all scrambled to be perceived as the candidate who would work best with Kathleen Wynne. Up next: Collaborating with Metrolinx and the GTA’s municipal leaders to solve transportation and congestion woes, which cost the region at least $2.7 billion a year.

Toronto's 50 Most Influential: John Tory
John Tory, 60
City Hall

And people said it couldn’t be done. Tory, the perennial nice-guy-who-always-­finishes-last on election day, finally pulled off the win of the century—becoming the city’s 65th mayor and putting an end to the farcical Ford era. Throughout his campaign, Tory reminded us that Toronto politics can, in fact, be practised without racial slurs, drunken rages or thuggery. He’s known as a consensus builder, which, at this critical juncture, may be the single most important qualification for mayor. Toronto, despite its economic heft—­responsible for 10 per cent (or $157 billion) of Canada’s GDP—is a divided city in serious need of repair. Tory has the clout not only to lead his 44 colleagues on council, but also to persuade the heads of the provincial and federal governments to back his plans for transit, infrastructure and affordable housing. This is an opportunity for the city to right itself, and it can’t happen soon enough. Fortunately for us, Tory seems like a man in a hurry. Friends in high places: Kathleen Wynne, Charles Sousa, Brad Duguid, Lisa Raitt, Stephen Harper—who called Tory to meet with him last summer.

(Photographs: Tory by Markian Lozowchuk; Wynne by Luis Mora; Cope courtesy of Bell Canada; Laurence; Quan by GetStock; Drake by Reuters; Bailey courtesy of TIFF; Thomson by Getty Images; Keesmaat by Daniel Ehrenworth; Wiseman courtesy of CPP)


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