This past summer, ESPN The Magazine, in its annual ranking of sports franchises, identified Toronto as the worst city for sports in North America. Inevitably, the assessment provoked a fury of denial. Brian Burke, the Toronto Maple Leafs’ president and general manager (and probably the best executive in the NHL) called the ranking, “absurd and offensive” and went on to claim, “I don’t think ESPN knows squat about Canada. I don’t think they know squat about hockey.” I suppose Burke had to say that, being GM and all, but it was still an embarrassing comment. No sane person could disagree with that ranking. As Burke must know, the only problem with ESPN’s analysis is that it focused almost exclusively on quantitative matters, the “bang for the buck,” meaning the money gathered from tickets, concessions, and parking compared against the team’s wins. Being a Toronto fan is so much worse than any algorithm could ever express. A merely numerical measurement fails to capture the daily spiritual trauma of following sports in Toronto.

It’s a given that the true fan goes to games not for the necessarily occasional thrill of winning, but for the quotidian experience of losing — a truth articulated originally and beautifully by Nick Hornby in Fever Pitch. Losing in Toronto, however, is an unremitting condition. The CFL team, the Argonauts, is so bad that when I recently found a friend of mine betting on it, I immediately wondered if it was time for an intervention about his gambling addiction. As it stands, the Argonauts are 2 and 6 3 and 9. The Blue Jays this year aren’t completely terrible, but when you’ve said that, you’ve said everything. They may be a rising power in the East, as many claim, but they sure haven’t risen yet. The Raptors are still in their post-Bosh wilderness (not that the Bosh period was a golden age), and Toronto FC currently rests at the bottom of the Eastern Conference. The Leafs, who matter to Torontonians more than all the other teams combined, have not won the Stanley Cup since 1967, and they haven’t made the playoffs in a franchise-record six seasons. The only team with a longer dry spell is the Florida Panthers. The Leafs’ major source of hope seems to be Brian Burke himself, but when the major source of your dreams is a front-office guy, you are in a dark place. Cheering a GM, to me, is hitting rock bottom.

And this in Canada’s biggest city, where hockey matters more than baseball in Boston or basketball in Indiana or football in Texas. The only other places where sports dwell so near the most profound and abiding national questions are rugby in New Zealand, which recoups the warrior culture of the Maori, and football in Buenos Aires, where the slumdog Boca Juniors battle the uptown Millonarios in a never-ending class war. Maybe Real Madrid against Barcelona could be added to that list, but nobody else. People who were surprised that Vancouver burned after the Stanley Cup playoffs last year are unaware of the history of the sport in Canada. Of the 10 biggest riots in Canadian history, six began at hockey games.

During the 2010 Olympics, more than 80 percent of the country watched the men’s hockey finals. Our current Prime Minister, Stephen Harper, is legitimately an expert on the history of the game; the only reason he hasn’t finished his book on the early days of the NHL is that he’s been busy running the country. The history of the game and the history of the country are much the same thing: You can trace the rise of Quebec separatism, for example, to the Rocket Richard riots in 1955. On the other hand, hockey is the one mass-media phenomenon for which English and French Canadian have the same stars — not true of any other form of entertainment. Immigrants join hockey as fans and players as soon as they join the Canadian middle class. More than a hundred thousand people watch Hockey Night in Canada broadcast in Punjabi.

All of which is to say, we are so terrible when we should be so great. I wish I could say that the misery in Toronto follows that simple equation: the size of our passion divided by the grossness of our losses. Unfortunately, the torture of watching hockey in Toronto is nowhere near so easy. Everybody knows that Toronto loses not despite our love for the game, but because of our love for the game. The truism is by now well established, a local media commonplace. “Each man kills the thing he loves,” as Oscar Wilde put it. The teams lose because they don’t have to win. The Leafs have so many people on the waiting list for season tickets that they don’t take new names anymore; no matter what happens they have a 99 percent renewal rate. Torontonians line up to pay tens of thousands of dollars to watch some of the most dreadful hockey played at a professional level.

So who can blame Maple Leafs Sports and Entertainment, the business that controls the Leafs and the Raptors, for following that oldest and truest of rules: Never give a sucker an even break? The most recently released financial reports, published by the Toronto Star in 2007 and which were neither confirmed nor denied by the privately held MLSE, suggest they run a profit margin of more than 20 percent. Before we start hacking away at the irresponsible evil-capitalist angle, however, we should recognize that the majority shareholder in MLSE is the Ontario Teachers’ Pension Fund (although they are currently looking to sell); the profits of MLSE have paid for the retirement of a lot of hardworking people, so it’s good that they’re good at business. And they are excellent business people.

Nonetheless, I don’t know how the executives at MLSE eat and sleep and walk around knowing how egregiously and consistently they have failed their city. For the past 14 years, the head of MLSE has been Richard Peddie, a mostly cheerful public figure with a hefty amount of charm and a disarming sense of humor. Of course, part of me wants to pin all those 14 disastrous years of failure on him. His retirement agreement stipulates that if Toronto wins the Stanley Cup in the next three years, he receives a championship ring. I have a better idea of how we should celebrate his upcoming departure: with an inverted statue, his image carved underground, a Peddie-shaped hole that all the fans could fill with leftover beer (or borrowed beer) in commemoration of all the victories he did not bring us. The names of all the vice presidents during his tenure could be carved there, as well.

Ultimately, Richard Peddie makes an unsatisfying scapegoat, though. In interviews and on television, he seems like a decent guy who’s excellent at his job. At worst, he may be an embodiment of the Canadian technocratic blandness that concentrates on efficiency and deprecates personal glory. This same blandness is why Canadian banks are the most dependable in the world, and why, while the rest of the West is falling apart, we more or less have maintained a working government and a secure middle class. Besides, it’s too easy to blame Peddie. It’s too easy to blame MLSE even. The tragedy of the Maple Leafs runs much deeper.

The problem with hockey in Toronto is the nostalgia that dominates how the game is played and consumed here. More than winning, Torontonians love the style of old-time hockey, a spirit of straightforwardness, brotherly violence, and what for lack of a better word I will call “not-fancyness.” Hockey commentators here love nothing more than explaining how hockey games are won by cycling the puck, driving at the net, ugly goals. “They don’t look pretty, but they win games.” They love saying that.

Despite having more money than any other hockey team in the league, the Leafs have not purchased any brilliant players in an era overflowing with brilliant players. What the Leafs specialize in is the great bush-league heroes — this is not an accident nor is it the fault of the suits. They know what their audience wants and they give it to them. The city never took to Mats Sundin, the magnificent Swedish all-rounder. The fans adored local boy Tie Domi, a butcher on skates. His definitive moment, perhaps the definitive moment of the Leafs franchise in the 21st century, was his entirely gratuitous hit on Scott Niedermayer in the dying seconds of Game 4 of the 2001 Stanley Cup second round. At the end of a game in which Toronto tied the series, Domi’s dirty hit handed the momentum over to the Devils, ruining the best chance the Leafs have had in living memory to make the Finals. The symmetry is nearly perfect: the size of the failure matches the depth of a moral disaster.

Toronto fans like extravagantly ordinary players. How else to explain paying $3 million for Darcy Tucker? Or $5.5 million for Bryan McCabe? Sometimes I wonder if Toronto would even know what to do with the Sedin twins, who are less like quick-fisted farm boys and more like magical changelings conceived by elves in the Scandinavian forest. Would they even be welcome in Toronto? During the 2011 Stanley Cup, everyone felt they had to cheer for Vancouver — Canada’s team — but secretly everybody wanted Boston to take it. The choice between Ryan Kesler and Tim Thomas wasn’t really a choice at all, even if Thomas is American. I recently overheard a conversation in a bar about whether Sidney Crosby would ever return to hockey, and one guy said, “I told you he was made of glass.” That’s typical; Toronto wouldn’t take Sidney Crosby even if he were on offer. Not tough enough.

This bush-league spirit extends from hockey to all other sports. Chris Bosh, who was adored when he played here, was a great Toronto story exactly because he was so hard-working and not at all stuck up or sophisticated. He wasn’t great, but he was doing the best with what he had. In 2007, when Toronto FC arrived in the city, many believed that it would break the cycle, but the city is full of English and Italians and Portuguese and Trinidadians and Koreans who are so football-crazy that TFC doesn’t have to win. The situation with the Leafs has been replicated nearly perfectly, the process beginning in its very first season. TFC’s “star” player then was Danny Dichio — one of the slowest football players in the league. (Watching him play made it seem like your TV was broken just in the spot where he was playing. It looked like he was running through treacle.) Eventually, in TFC’s fifth game, he scored the team’s first-ever goal, in the 24th minute, and thereafter TFC fans sang the Danny Dichio song at minute 24. In the last game of that season, down 2-1 with nothing on the line, Dichio managed to catch a late ball and flick it over the keeper, which sent the Toronto fans into a hysterical frenzy. A midlevel player fluking the ball to achieve a meaningless draw — when you cheer such mediocrity, why should anybody give you anything better?

You may wonder: Why would anyone want to be a part of this? The answer is that there’s little choice in the matter. My son first told me he was a Leafs fan when he was 3 years old. At first I was horrified; I wanted to shelter him, hoping it would all blow over. But lately I’ve realized that it’s important for him to know this pain, so I bought him the Maple Leafs pajamas he thought he wanted. It’s important for him to suffer with the city he lives in. Because suffering for a lack of beauty is right and proper. The bush-league spirit that infects Toronto’s hockey also infects the rest of the city. We are a big, nasty, rich city that insists on acting like a small town. We’re the size of Chicago, but how could you tell? Our mayor would be an amazing mayor for about 20,000 people. Our museums, our architecture, reflect little of the immense resources that flow through the city from half a continent. Our transit system is a joke because we refuse to plan for our success. It is obvious that Toronto won’t be whole, won’t begin to live properly again, until the Leafs win the Stanley Cup.

In the meantime, we deserve to lose. We deserve our pain. The pain is the only hope that we’ll ever learn to win again.

An earlier version of this piece listed the Blue Jays as one of the teams owned by Maple Leafs Sports and Entertainment.

Stephen Marche is a novelist and a columnist at Esquire magazine. His most recent book is How Shakespeare Changed Everything. You can follow him on Twitter @stephenmarche.

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