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Toronto Raptors Global Brand Ambassador and rapper Drake

The Toronto Raptors Global Brand Ambassador and megastar rapper, Drake has helped put basketball in Toronto on the map.


Talking up Toronto is a responsibility Drake takes seriously. He'll do just about anything to show the city well. The internationally famous rap star is affected by his sense of place and has widened the imaginative landscape of the city

In order to get from press row down into the bowels of the Air Canada Centre after a Toronto Raptors game, you have to walk past the team locker room.

Some nights, Drake is standing there, slapping backs as the players come off the court. When they win, he's hooting. When they lose, he is suitably mournful.

An MC in more senses than one, Drake is unusually adept at mimicking moods, approaches and verbal gambits. If you're up, he's up. If you're street, he's street. If you're someone's uncle or accountant, he can sound like an ambulating TED talk.

One night, I fell into line behind a slow-moving trio of Raptors assistant coaches. I was rushing to get past the logjam. We turned a corner. Drake was standing there by himself, waiting. He had the look of someone encountering a delightful coincidence.

He bent deferentially at the waist, offering each man a strong Bay Street handshake with impressive eye contact: "Good game. Good game. Good game."

I was bringing up the rear, now at a small distance. Drake knew I wasn't a coach, or anyone else who mattered. There was a beat that would've allowed him to turn away without causing offence.

I tried to blast past and save him the trouble, but he angled himself slightly so that I had to stop altogether.

Hand out. Full eye contact. Firm shake. "Good game," he said. "Thanks," I said, stupidly. Then, eyes still locked, he stepped back so that I could continue on.

At the time, I thought the gesture very Canadian. Now, I think it was something more than that. Drake has spent most of his career taking personal ownership of Toronto and its brand.

Drake, right, celebrates with Kyle Lowry of the Raptors after Toronto beat the Cleveland Cavaliers on the third annual Drake Night at the Air Canada Centre.

Drake, right, celebrates with Kyle Lowry of the Raptors after Toronto beat the Cleveland Cavaliers on the third annual Drake Night at the Air Canada Centre.

Darren Calabrese/The Canadian Press

It would be wrong to say he has reshaped the global perception of this city. That would suggest there had been any perception at all.

Until Drake decided to make it his quixotic mission, Toronto did not exist in the imagination of the wider world. If it does now, it is almost entirely through the lyrical lens of a 29-year-old from Forest Hill.

Talking up Toronto is a responsibility Drake wears like sackcloth, with religious zeal. He'll do just about anything to show the city well. Even sharing special moments with random passing schlubs after the basketball game.

The man in charge of the city

Drake's first appearance as a quasi-official civic representative came in mid-September, 2013 – at the announcement that Toronto would play host to Sunday's 2016 NBA all-star game. This was shortly after the Raptors had named him their global brand ambassador.

Drake was plunked on a riser beside mayor Rob Ford. It wasn't what most people would consider a flattering photo op.

Four months after the first reporting of his crack video, Ford was entering the weightless stage of public free fall. He looked the part, moistening under the klieg lights. Rickety high chairs had been placed too close to one another. Ford was seated practically in Drake's lap. He kept screwing himself into place, tugging uncomfortably at his suit jacket.

Drake noticed. Before proceedings began, without saying anything, the younger man reached over and began gently petting the jittery older one. On the back, the shoulder, the knee. Ford visibly calmed under these small gestures of affection. By the time things got under way, the doomed mayor looked as though he might be having fun.

The news conference was the usual corporate jabbering, with one real takeaway. That you had just seen the man in charge of the city. And it wasn't the guy who had won an election.

Is this the point where we should talk about why Drake loves Toronto so much? Because there is no good answer to that question.

Drake tries. He is rarely interviewed, but when he is, the topic comes up: "When I think of myself, I think of Toronto." Beyond personal geography, it's hard to understand why this feeling is so intense. I'm from Toronto. I like the city a lot. I've never known anyone who likes it this much. Perhaps because the rest of us have to ride the subway.

Drake created his own musical subgenre out of being unlucky in love, but the city, rather than any person, is his Beatrice. Having known her when he was young, he can never forget her.

"Somebody has said that we're a city that needs permission to love itself," says Matt Galloway, the host of the city's most important radio show, CBC's Metro Morning. More than any other public figure, Galloway may be Toronto's civic conscience and a mutually agreeable arbiter of what does and doesn't matter here.

"I was at a pub watching football. A guy walked up and said, 'You're Matt Galloway. I listen to you on the radio. This place isn't nearly as good as you say it is. I've lived in London and I can't believe that you'd say this place is so great.' This is a Torontonian who's saying this! Can you imagine if you were in New York or London or Boston or any other great city and someone said that to you? There'd be a fistfight. But here, of course, you feel sheepish saying that you love the city.

"Drake has given people permission to do that. He stands out because he's so genuine about it. What's the secret? That he doesn't have to do it. But he did it anyway."

"I started to notice it a few years ago," says Cameron Bailey, artistic director for the city's most renowned cultural export until Drake arrived, the Toronto International Film Festival.

"When I go to Los Angeles or some film event somewhere in the world and you're sitting at lunch with someone, Toronto can be a topic of conversation and they have something to say about it. It used to be a blank stare. Drake did that. He put this city on the map in a way no one else ever has."

There is a rich history in hip hop of taking an iffy place and making it sound like a twisted Shangri-la. Grandmaster Flash did it for the Bronx; Jay Z did it for the Brooklyn projects; OutKast did it for Atlanta – if you've been to Atlanta, you'll know that is a Pritzker Prize-level work of civic reclamation.

What those places have in common is that they are or were dodgy in an interesting way. They have a thwarted, underdog history.

Toronto doesn't have that. Or, at least, not one that is widely discussed among its inhabitants. Ten years ago, if Torontonians were to sit around the metaphoric bonfire singing songs about the people and where they've come from, it would be a track off Rush's 2112.

Requiring some wedge beyond music into the city's suburban diaspora and shifting demographic, Drake settled on basketball. This never seemed calculating. Back when the team was terrible – terrible with eight "r's" – Drake was its only booster with real profile. He even likes the wretched purple uniforms from the early days.

Drake went on ESPN's First Take just before the global ambassador role floated to the surface. In the context of a wider conversation about the NBA, he said, "The real goal here is to build up the Toronto Raptors."

Host Stephen A. Smith burst into laughter. Then he got quietly incredulous.

"The Toronto Raptors? Really? Really?!"


Drake had tried to involve himself with the team, but couldn't get anyone to return his calls.

Seeking a local spokesperson, incoming Maple Leaf Sports and Entertainment president Tim Leiweke went and found him. It says something about where the city was at that point that Justin Bieber's manager, Scooter Braun, facilitated the hook-up. It took two Americans to figure out what Toronto's most famous citizen meant to Toronto.

Leiweke and Drake arranged to discuss a partnership over dinner at MLSE's executive canteen, E11even. Leiweke took Raptors general manager Masai Ujiri along. Drake brought his DJ.

"I texted all my friends: 'I'm having dinner with Drake.' Nobody believed me," Ujiri said. "He captivated me. He was so passionate about the team, about the city."

This is saying something. Whatever Drake is to a city, Ujiri wants to be for a continent. His relentless boosterism for Africa has made him a formidable political power broker. Over the all-star weekend, Ujiri will host a symposium on Africa's future at the Art Gallery of Ontario. The keynote speaker will be Rwandan President Paul Kagame.

Ujiri visited Kagame's home in Kigali over the summer. Mostly they talked about basketball. Though one suspects he has more pressing business, Kagame had risen in the middle of the night to watch Toronto flame out of the first round of last year's NBA playoffs.

"I was shocked," he told Ujiri.

It's proof there is nothing that so attracts and disarms the truly powerful as sport. You see them panting around the Air Canada Centre's VIP suites, hoping to get a look at a real player. Whenever Drake floats in, they are all at pains to play it cool. The only people innocent and careless enough to get giddy in his presence are members of the opposing team.

Often, the financial power at the centre of this country is arrayed across the court in the form of the MLSE board: chairman and co-owner Larry Tanenbaum, Bell Canada chief executive officer George Cope and others. They sit almost exactly opposite Drake.

Occasionally, you'll catch them watching him, but not the other way round. They are technically his bosses. They are functionally his attendants.

One of the ways you can determine an alpha is to watch his smile. Important men will smile at people they perceive as subordinates. It is riskless gesture of magnanimity. They will not smile at their betters – it shows weakness. Watch the suits in the front row at a Raptors game. They aren't smiling.

Toronto Raptors general manager Masai Ujiri (L), rapper Drake, and President and CEO of Maple Leaf Sports and Entertainment Tim Leiwekea (R) pose after an announcement that the Toronto Raptors will host the NBA All-Star game in Toronto, September 30, 2013.

Toronto Raptors general manager Masai Ujiri (L), rapper Drake, and former President and CEO of Maple Leaf Sports and Entertainment Tim Leiwekea (R) after it was announced that Toronto would get the NBA All-Star Game.

Peter Power/The Globe and Mail

Except Drake. He's the only one down there who looks like he's having any fun. He's about the smiliest human you've ever seen. What does that tell you?

There was no financial calculation in Drake's new relationship with the Raptors. On the first day, he asked if he could get an MLSE office. He actually said that out loud as he walked the corporate hallways: "I get an office, right?" He did not. That would seem too transactional for all the nervous Nellies in the league who feared (quite rightly) that Drake was becoming the Raptors' talent wrangler.

When he provided complimentary OVO branded T-shirts for the first Drake night, they were hitting eBay at 200 bucks a pop before the game ended. Drake sold them to MLSE for wholesale cost.

"He does not make a nickel off any of this," Leiweke said at the time.

When he publicly flirted with star forward and soon-to-be free agent Kevin Durant, the league hit Toronto with a $25,000 (U.S.) fine. According to an MLSE source, the league made the Raptors an offer: Drop Drake and we'll drop the fine. The idea was dismissed out of hand. When the approach became news, the league denied making it. They've laid off Drake since.

Little wonder. He has since expanded his role to de facto league rep. He's much more than a mascot – which is what most celebrities end up being for the teams they support. Drake is a totem. He's the hybrid Hollywood star/youth culture whisperer/good corporate citizen that every major business concern would build in an underground lab, were such a thing possible.

Drake's relationship with the team's management structure has cooled over the past year, especially after Leiweke left. When he was initially invited in, he was offered the chance to oversee a complete redesign of the Raptors brand. Everything but the team name was on the table. Only once he had finished was Drake told that his suggestions were just that. Buoyed by success in the standings, the club decided to stick with its familiar colour palette and logos.

Peevishly, Drake took a little poke at the look on social media. He wasn't seen as often at games. He has spent many months working on an album that is beginning to feel like it may never come out. He has other things on his mind beyond Toronto and its need for his approval. It never got to the level of a fight, but it was obvious Drake was in a bit of a snit.

That ends this weekend, the culmination of Drake's involvement with the NBA. The all-star game is the intersection of hip hop and sport, meaning that it is the fulcrum of popular culture. No one has yet figured out a way to properly televise it – the dunk contest is the closest you'll get – but the streets of Toronto will be, for just a few days, the Woodstock of the right now.

Leiweke envisioned Drake as the city's greeter. You can imagine him, bent at the waist, hand out, eyes locked.

He has a few official duties, little stuff. It's rumoured that he has a rented manse in some leafy part of the city that will serve as a naughty NBA clubhouse. Apparently, LeBron James wanted to host that location, and Drake slapped him back. If so, it is his town.

That is the latest stage in Drake's development: guarding the territory you've marked off for yourself.

Over the summer, he was dragged into a convoluted spat with Philadelphia-based rapper and erstwhile collaborator Meek Mill.

While Mill frothed online, Drake kept his peace. The unlikely person who stepped in for him was 74-year-old City Councillor Norm Kelly. Kelly scolded Mill on Twitter. The image alone – "Old man yells at whippersnapper" – was so comedic, it rendered Mill impotent long before Drake had responded in song.

The cover of his most savage rejoinder – the one-off track Back to Back – showed Joe Carter's leaping trot when the Blue Jays won the 1993 World Series. Toronto over Philadelphia. It was all of Drake's passions colliding.

Kelly became a star out of it. It was arranged that the pair should meet before a surprise show at Ryerson University.

"The first thing I remember Drake saying to me was, 'You're my hero.'"

Kelly leans back in his chair, face alight with childish pride. We're sitting in his City Hall office. It's kitted up with enough Drake paraphernalia to make a decent shrine.

You can understand why he's enjoying this. This unlikely connection has turned him into hip hop's cornball godfather. Kelly's gift is that he's in on the joke.

But you get where Drake is coming from, too. After years spent defending the city, the city – speaking through someone pulling the levers of municipal power – defended him. Drake rushed out to embrace that person. What's a key to the city stood up beside that?

Drake seemingly makes these counterintuitive marketing calculations without any consideration of their marketing implications. Which is probably why they work.

The last word on him rightly rests with Ujiri. They are kindreds in important ways: proselytizers for a place; lovers of the same pastime; glamorous self-made men who are endlessly alluring to the 1 per cent of the 1 per centers. While he may not understand Toronto, Ujiri understands why Drake might care about it so much. He has the same obsession with home.

They talk often, usually by text. Drake switches out his phones regularly. On the rare occasions he calls, the ID pops up as "Drake New New New New Number."

Ujiri is retelling the story of how Drake called him in the middle of the night after Raptors centre Jonas Valanciunas was injured in a west coast game. He is twisting around in his chair, trying to get to the depth of the man.

"He is authentic," Ujiri said. "He's a real person. Please write that."

Maybe that's the allure, that in his relationship with the city, Drake gives, though there is nothing to take. That's what people mean whey they say he is "authentic."

To be part of this, you don't have to be interested in Drake's music or businesses or (very occasional) adventures in the tabloids. If you live in Toronto, you have been affected by his sense of place. He has widened the imaginative landscape of the city. He has taken a place you know just as well as he does, and reintroduced it to you in a way that makes it, and you, seem better.