Almost Daring to Dream
Almost Daring to Dream
In the span of a year, Canada’s largest city claimed a new lease on sporting life. But can it really shake its loser label without a title?

They’re like a fine wine—they cost too much and always end up in the cellar.

…The difference is, a mosquito only sucks in the summer.

…And then the Jays fan turns off his PlayStation and goes to bed.

You might not know the punchlines, but you recognize their target: Toronto. The city where good athletes go to cry.

In 2011, in the same month this magazine was born, Canada’s largest metropolis was ranked by ESPN as the worst sports city in all of North America. Yes, worse than Cleveland, which at the time was working on year 47 of not winning anything at all. A year later, in a similar survey, Toronto’s Maple Leafs were ranked 122nd out of 122 North American sports teams, and it was a feat they repeated twice more in the summers of 2014 and 2015. Breaking up those years of basement-dwelling, of course, was the club’s lone playoff appearance in a dozen years. And how did that end? Well, the Leafs were up 4–1 with 12 minutes to play…

This is the crux of Toronto sports: You read “Maple Leafs” and “4–1” and your mind does the rest, filling in images of the improbable, heartbreaking game-seven loss to the Boston Bruins—a sure signifier that the city’s sports ambitions have become synonymous with more than simple sporting failure, that Toronto’s inevitable misery has become a touchstone, as scripted and assured as a rom-com’s ending. As recently as 2010, those same Bruins had choked away a three-games-to-none playoff series lead, just the third team in NHL history to collapse in such humiliating fashion. In 2014, the San Jose Sharks matched that feat. Those are, as a point of fact, more historic failures than the Leafs’ first-round defeat. But I had to look up the exact contexts of those flameouts, and most likely you would have had to do the same. The 2013 Maple Leafs, though? It was 4–1…

Out for the count
The Maple Leafs’ game-seven loss to the Bruins in the 2013 Stanley Cup Playoffs is the embodiment of Toronto sports fans’ pessimistic thinking

This is the mindset with which Toronto’s collective sports psyche has done battle every day, in every game, in all of those small-but-critical moments on which a contest can swing, for most of the past two decades. The enemy is sinister and implacable—it is the belief that even the most optimistic scenarios are not to be savoured lest they rot on the tongue; that not only will defeat be snatched from the jaws of victory, but that the manner of defeat will be spectacular enough to warrant canonization; the belief that all victories will be pyrrhic, merely steps on the road to something worse. To be a Toronto sports fan one year ago, on July 30, 2015, was to have the ending spoiled but always be watching anyway: You know it’s going to be horrible but you have to tune in to find out exactly how.

The litany is easy to compile and staggering to contemplate: In 2011, not one of the Maple Leafs, Raptors, Blue Jays, Argonauts or Toronto FC qualified for the playoffs—no, not even the Argos, who missed a six-team playoff in an eight-team league. Four years later, things had not improved at all. TFC was still without a single playoff appearance in team history. The Blue Jays were the mortified new owners of North America’s longest pro-sports playoff drought. The Raptors had never won a seven-game playoff series, and had turned two straight division titles into two first-round losses, the most recent one a sweep. The Leafs were still Cupless since ’67, incapable of winning, and incapable of losing badly enough to help them win later. And the Argos, despite the heights of a 2013 Grey Cup win, could not even fill a stadium to half its capacity in the centre of the country’s largest city, the only team in the CFL to suffer that level of indifference.

But then, in ways both sublime and subtle, things started to change. A trade here, a winning streak there. A new coach, a new building, a bat flip. A comeback, a killer instinct. A few smart moves. A little luck. Slowly, at first, then rapidly—as though hope were infectious—high-level athletes began to realize that playing in Toronto was not a sentence to sporting purgatory. And then the fans, even more slowly, began to believe it, too—and now their collective confidence, while still fragile, at least exists. Since July 30, 2015, the day the Blue Jays acquired David Price from the Detroit Tigers in exchange for pitching prospects, three of the four major Toronto teams have reached heights not seen in decades, if ever. Of the four major North American leagues in which the city competes, a legitimate case could be made that the very best players in two of them ply their trades in town.

Meanwhile, the worst team in the city reached its all-time nadir—only it was widely hailed as their best season in years—and its minor-league affiliate team set a franchise mark for victories and finished with the league’s best record. Even the Argos, the city’s sixth team and forever the runt of the pro litter, finally opened a season playing football on real grass and allowing fans to tailgate outside, ushering in an era that might see them step gingerly onto the path toward relevance. Can this sort of rapid reform really turn a city of sporting cynics into believers? Is it too soon to buy in?

There are no titles to show for any of this, of course. Yet. But Toronto sports culture is changing and all the punchlines in the world won’t stop that from happening. In 2016, professional sport moves faster than decades-old narratives, and at long—like, really long—last, Toronto has a chance to become one of North America’s biggest sporting success stories. The money is here, the stars are here, the structure is here, and that means anything is possible, even a parade down Yonge Street.

In the past year alone, each of Toronto’s three most beloved-slash-cursed teams made a decision that broke with their recent tradition and, more importantly, against popular expectations—and all of them reaped tangible rewards for it. In short, for an entire year, the best-laid plans of Toronto sports teams… worked.

David and goodbye-eth
Price played a major role in getting the Blue Jays to the ALCS in 2015—but not overpaying to keep him was the right move

The Toronto Blue Jays and David Price and savvy

The best way to chronicle this series of strange plot twists is with a calendar, and this one begins with the Jays’ long-awaited return to genuine World Series–contender status, driven by the acquisition of Price from the Tigers last July. He was gone three months later–the only ERA he represented in Toronto being 2.30 over 11 regular season starts–in one of the best non-moves in the recent history of the Blue Jays. It wasn’t his continued presence that mattered to the Jays, but what his coming and, perhaps more importantly, his going, represented. Good teams pay premiums to rent players who leave town quickly—and paying for Price not only made the Jays a better team, it meant the organization saw itself as the sort of team that rents pitchers of his calibre.

And when Price arrived and pitched well, the Jays players began to see themselves as the sort of contender that might go all the way—after all, they’d gone and rented themselves an ace. And when the Jays went on a second-half tear and came within two games of the World Series, that meant the fans could believe that this sort of move could pay off. Price didn’t arrive, pitch badly, sit idly by in the dugout as the team missed the playoffs and then skate with nothing but a few bags of popcorn to show for it—which, if they’re being honest with you, is the movie that played in many a Jays fan’s head in the days following the trade. That would have, after all, been the Toronto thing to happen. This city’s fans still remember the Maple Leafs careers of Brian Leetch and Owen Nolan.

And if not an ignominious exit, the other Toronto ending to this story would have been to happily overpay the big name who’d sold big tickets, only to see it all go downhill—to wake up in July 2016 and find Price midway through the first year of an incredible $217-million deal with a 4.51 ERA, having allowed more hits than any other pitcher in baseball. Being swayed by a surprising run into overpaying and over-committing is also a hallmark of this city.

Instead of either extreme, though, the 2015 Blue Jays did something different, something winning teams do all the time but is rare enough in Toronto to cause double takes. They paid for their rental, then let him make his money elsewhere and used the cash to sign two players who offered more bang for the buck. Price and his career-worst 2016 season now reside in Boston, and for less than the $30 million he’ll earn this year, the Blue Jays are paying J.A. Happ ($10 million) and Marco Estrada ($13 million)—and each is having a better year than last season’s big-name acquisition.

This anecdote would not be earth-shaking to contemplate almost anywhere else. Big-money free agents sometimes disappoint, and bargains are everywhere if you’re able to properly assess talent—it’s just that, again, this is Toronto.

Not feeling blue
Winning the NHL Draft Lottery—and the rights to Auston Matthews—was the Leafs’ reward for sticking with a slow rebuild, something previous regimes wouldn’t do

Mike Babcock and the Toronto Maple Leafs and sufferance

One of the things you have to understand about the former worst sports city on the continent is that its trademark horn-honking after Leafs wins only became a real joke in the past decade. The city was, for a very long time, host to the most unironic and unnecessary celebratory blaring on the continent. Did the Leafs win the second game of their first-round playoff series? Sound the horns! The way Maple Leafs fans joke about Montreal hockey fans overturning cars is the way Leafs fans actually blared their horns. Maybe it’s something to do with the nature of Toronto’s traffic putting drivers on very familiar terms with this form of expression, but in recent years, on April nights downtown, the silence can be deafening—and that’s where jokes about honking after a win in December come from. They are born, like so much of Toronto’s recent fan behaviour, out of self-mocking desperation.

There’s no question that a Leafs fan’s plight is one of the most unsympathetic in sports. Their team has every built-in advantage, and has squandered most of them in favour of the short-term sating of competitive appetites. As a franchise, most iterations of the Maple Leafs’ front-office brass would have failed that traditional child’s test for understanding delayed gratification.

So, naturally, when the team’s four most important decision-makers each prepared the fans for a horrible season before it even began, skepticism abounded. What if the team got off to a hot start? What if the fans stopped coming, or worse, kept throwing sweaters and waffles and other things? What if they were really only a half-decent season followed by a free-agent signing like, say, maybe Steven Stamkos, away from being a legitimate contender? “If you think there’s no pain coming, there’s pain coming,” the man hailed as the best hockey coach on the planet famously said. And lo and behold, the NHL’s most reactionary franchise stuck by Mike Babcock’s words.

“If you think there's no pain coming, there's pain coming”

The day before opening night, William Nylander, Kasperi Kapanen and Connor Brown—the Toronto Marlies’ best scorers and the Maple Leafs’ best scoring hopefuls—were sent to the American Hockey League team. None of them would see NHL action until the season was all but over—and even then Nylander was up only long enough to get a taste, and Leafs fans can still dream of a Calder Trophy for him.

The details of the season don’t matter, but few people watched, and nothing was won. Never before has a management team taking over a profitable company announced their arrival with promises of failure and then been cheered for delivering on them. On April 10, the Maple Leafs finished their season last in the NHL. On April 14, the team signed Morgan Reilly and Nazem Kadri, the two most important young players on the big club, to extremely sensible six-year contracts. On April 30, they won the NHL’s Draft Lottery and on June 24, they used the No. 1 pick on Auston Matthews, the surest-thing young centre this side of Connor McDavid and Jack Eichel.

Even trigger-happy Torontonians don’t generally honk for draft selections or contract extensions, but when they can be taken as a sign that the light at the end of the tunnel might not actually be a train, perhaps they should.

Eyes on the prize
Lowry and the Raptors rewarded their GM's faith in them by making the Eastern Conference finals for the first time

DeMar DeRozan and Kyle Lowry and patience

If you think the fans in Toronto are angry, you should read the columnists. The Raptors’ first-round playoff sweep at the hands of the Washington Wizards in April 2015 was described as both “a cascading failure six months in the making” and “a remarkable mess,” and meant that it was “time to blow this team up.” Perhaps most damning—and emblematic of public sentiment—was when one scribe determined, while looking at the roster’s makeup, that “there is nothing essential here.”

It was nearly a foregone conclusion that GM Masai Ujiri would not bring back a team led by DeRozan, Lowry and Jonas Valanciunas—that two years of Atlantic Division titles followed by embarrassing exits had proven that such a core was a losing proposition. Except to Ujiri, who firmly believed in his group and was willing to withstand a summer of scorn and a season full of people saying, “Yeah, but…” Of all the major Toronto sports executives, Ujiri’s path was the simplest to navigate over the past year—he had two stars, an easy division for the taking and money to spend on a free agent like DeMarre Caroll—but perhaps the hardest to actually walk. The Jays had rewarded their long-suffering fans with some playoff success, while the Leafs were not expected to even sniff the playoffs. Ujiri knew he had a playoff team, but not one that could necessarily win in those playoffs—and nearly everyone else in the city was convinced that it couldn’t.

Scrapping the plan and starting over, with DeRozan a year away from free agency and expected to get a maximum contract that most of the city would have resented anyway, would have been a surprisingly popular move. Hell, with the Leafs committed to pain, and with Toronto awash in public sentiment for “rebuilding the right way,” Ujiri might even have dealt his two stars, fired his coach and been hailed for it.

Instead, he trusted them and was rewarded. The Raptors won two game sevens and lost a game six in the span of a month. And next season, maybe, after coming just two games shy of the NBA Finals, Raptors fans will believe in his vision.

We tend to think of the sporting identity of a city as something earned honestly, something that sticks for decades, like a high-school nickname, something that can only change as a result of years-long extremes. But that is the thinking of bygone eras, back when teams relied on local pipelines for talent, and when a team’s financial success was largely dependent on its geographic base—from sponsorships and seat sales rather than a cut of multi-billion-dollar national TV deals. That was when many things related to your favourite team, from ownership to players to salaries to logos, changed slowly, if at all. That’s how we’ve defined franchises for a long time. The Red Sox have been far more successful recently than the Yankees, but in that matchup they’re somehow still the underdogs tilting against the Evil Empire. Joe Louis Arena was the home of the “Dead Things” until well after Steve Yzerman brought the franchise back to competitive relevance, and it is still “Hockeytown” today despite close to a decade of mediocre results and announced attendance figures that are contradicted by a quick glance around the arena. It is why the same questions that dogged Peyton Manning through the first half of his career will now dog Andrew Luck, for no other reason than geography. It is this sort of inertia that might keep an invisible shoe forever hovering in the air above Toronto’s downtown core. But that thinking is as relevant in sports today as the enforcer, wooden rackets and relying on the eye test—you can still use them if you want, but every time you do, the results will make you look even sillier.

One last joke: Ever hear the one about how 10 years ago we had Johnny Cash, Steve Jobs and Bob Hope… and now we’ve got no cash, no jobs and no hope? It was born in the wake of the recession that started with the financial crisis of 2008 and spanned through 2011, at which point everything started to recover quite rapidly—but we’ll be telling that joke for decades, changing only the length of time. And they’ll keep telling those jokes about Toronto, too, right until the Cup finally rides down Yonge Street—but that doesn’t mean things haven’t already changed.

Photo Credits

Tom Szczerbowski/Getty Images
Brian Babineau/NHLI via Getty Images
Nathan Denette/CP (Price and Matthews)
Ron Turenne/NBAE via Getty Images