Playoff failures, rising ticket prices, frustrated fans. How did we get here? An inside look at Toronto’s miserable sports scene

Stretch back further, and this is its own low point. Of the 12 cities with pro teams in the NHL, NBA and Major League Baseball, Toronto sits at the bottom with one championship in those sports in the past 20 years, tied with the James Dolan-poisoned pool of New York, and the generously booed teams of Philadelphia. Sure, Los Angeles is a different animal — six teams, L.A. weather and glitz, seven titles in that span — but more comparable markets like Boston and the Bay Area each have seven, Chicago has five, and Miami three, including the Florida Panthers’ recent run to the Stanley Cup. Even sad-sack Washington and Dallas, little ol’ Denver, and poor old Detroit — with no playoff series wins by the Red Wings, Pistons or Tigers in the past decade — have two apiece.

Then there’s Toronto, where, to paraphrase Tolstoy, every franchise is unhappy in its own way, at a time of widespread organizational continuity. Brendan Shanahan has been running the Leafs since 2014; Mark Shapiro has been in charge of the Jays since 2015. Masai Ujiri, who brought a championship to Toronto five years ago, has run the Raptors since 2014.

Yet the season-ticket prices continue to rise and fan disappointment mounts. The Star has decided to examine how we got here, how the city’s three dominant sports franchises arrived at their individual unhappy places: who is to blame, how the city acts as a backdrop and perhaps a driver. Every failure in sports is collective and it can be about the owner, the management, the players or, in some cases, the town itself.

There is no one catch-all to explain it, of course. First, it’s not like you can’t win in this town. The Raptors proved you could, in 2019. The Jays have back-to-back World Series banners, a little worn, but adored.

And yes, all three teams play in completely different versions of Toronto. The Raptors remain a sort of outpost: they’re much less isolated than they used to be, but the NBA is still a mostly American league and there are barriers to surmount. The Jays can attract talent, but it requires big swings and for years Toronto has been jammed into the toughest division in baseball, between the Yankees and the Red Sox and the Tampa Bay Rays. It’s a rough neighbourhood.

And then there are the Leafs, for which there are almost no exact comparisons in pro sports. They have the biggest fan base in hockey, by miles; only the Montreal Canadiens have the population base and history to come close. There is also no team with a combination of that level of fan pressure and adulation, combined with Toronto’s historic weight of failure. Harold Ballard sold the Stanley Cup banners, and used some Cup pennants as tarps while repainting Maple Leaf Gardens, and that summed up several decades of the Leafs: a naked money grab, carelessness tipping into malice, the trashing of a public trust by a small man. Former Star sports columnist Dave Perkins used to browse the criminal records of the Maple Leafs directors and found, as he once put it, “fairly high incarceration rate, slightly lower on recidivism.”

Toronto has a rich history, but sometimes it’s just a history of the rich. It’s almost a catechism in this town: the last time the Leafs won a Stanley Cup was the last time there were only six teams in the entire NHL, and the franchise hasn’t even reached a Cup final since 1967. And despite Canada’s 31-year national Cup drought, Calgary, Edmonton (twice), Ottawa, Vancouver and Montreal have all played in the Stanley Cup final since 2004. Even the nascent Winnipeg Jets reached a conference final more recently than Toronto, in 2018.

The Leafs have won one round in the Shanahan era, and managed to feel worse for it within weeks. For all the talk about winning a Cup in Toronto, there wasn’t a very high bar to clear to make this feel like success in this city. They still failed to clear it.

So what is success? For whom? For fans, you want regular-season games to involve wins, yes, and you want playoff wins. For the owners there’s the money, which keeps rolling in, since Toronto is a top-five metro area in the North America pro sports sphere and the only one in the top 15 without an NFL team to suck away money and attention.

Have the Jays been successful? They played playoff games in three of the past four years, which the franchise hadn’t done since the glory years of ’92 and ’93. Perhaps that should be considered success?

Of course, these Jays are also managing to falter in frustrating fashion while actually spending money, and also won as many playoff games in their last three appearances as they did between 1994 and 2014. Small detail, that. The Jays are, mostly, a beacon of mediocrity: since 1993 they have finished first in the division once, second three times, fifth four times, and finished third and fourth a combined 22 times. Even the sad-sack Baltimore Orioles have more division titles since 1993. This year, on a team that pursued Shohei Ohtani and then just didn’t try any kind of sizeable Plan B, they’re just bad.

Have the Raptors been successful? Absolutely. The 2019 title was a masterpiece of team-building, memorable greatness and just enough luck, and that flag will fly forever. But the trajectory since has been an inarguable decline: the Raptors were a second-round team in 2020 in the bubble — and could have challenged for another title had a couple details changed — and have since come apart, losing Kyle Lowry, Fred VanVleet, Pascal Siakam and OG Anunoby in order to start what is expected to be a multi-year rebuild.

This year, between the Siakam and Anunoby trades, the Knicks lawsuit, the Jontay Porter scandal, a loss to snap the Detroit Pistons’ record losing streak of 28 games, injuries aplenty and the loss of their first-round pick to cap a lamentable trade for Jakob Poeltl, the franchise fell to a low that hasn’t been seen in a very long time. (And raised ticket prices, natch.)

The Leafs, though, remain an opera, sung mournfully over generations: an indictment of the greed of Toronto, or the fat-cat impotence of Toronto, or of the mercantile bloodlessness of Toronto. They hadn’t reached eight straight playoffs since the early 1980s, back when nearly every team got in. They are one of two teams to make the playoffs each of the past eight years, along with Boston; no team has scored more regular-season goals over that span and only two teams have had better power plays.

And only four franchises have won fewer playoff series in that span: Minnesota and the L.A. Kings are a combined 0-for-10 in series since 2017, and the Buffalo Sabres and Detroit Red Wings haven’t made the post-season at all. And if then-assistant Paul MacLean was talking about the ghosts and demons that haunted these Leafs in 2021 — after losing four straight playoff series, three as the underdog and three of which came in the deciding game — then how much does the accumulated pressure affect them now? With the Leafs, Toronto isn’t just the city — it’s The City. Being a Leaf is a cultural weight, and even if Auston Matthews and Mitch Marner and William Nylander and John Tavares and Morgan Rielly proclaim not to be haunted by 5 1/2 decades of failure, it’s the last decade of failure that belongs to them.

So ticket prices keep rising, and the franchises become ever more elitist cashboxes, and the biggest three teams in the city continue their frustrating paths. In this era of increasingly painful stability, what would it take for an executive to be replaced? For real change?

The Raptors showed better truly was possible. The Leafs got back to the playoffs and spoke openly of chasing the Cup again, although less so now. The Jays reached the playoffs, at least.

But maybe that’s why this era hurts and might hurt worse than the lost years in the first decade and a half to start the millennium. During the decade between about 2004 and 2013, the only good thing about Toronto’s sporting failures is that at least they came with what were, logically, low expectations. That was the decade of John Ferguson Jr. and Brian Burke and Dave Nonis, of Rob Babcock and Bryan Colangelo, of J.P. Ricciardi and the early career of Alex Anthopoulos. It’s been bad here before, but at least your hopes stayed comfortably low.

Now — with a Leafs team filled with stars and talk of chasing Cups and all those playoff chances, with a Jays team back in the playoffs after the all-too-brief Bat Flip era reminded fans how energizing it could be when this baseball team is good, after the Raptors went from playoff also-ran to the first big three championship in Toronto since 1993 — it’s like these teams are reminding their fan bases how painful hope can be. Maybe that’s worse, after all.

In a five-part series, the Star will examine how we got here: how the Raptors fell from grace, how the Jays went from a near contender to a bottom-10 mess, how the Leafs went from promise to a continuation of a civic curse. You can argue Toronto deserves better. What Toronto is getting, though, is something else.