So what now? Pressure is on Leafs, Raptors and Blue Jays to deliver, and the winning formula is simple

And so you get a city whose regular-season performance has been admirable, and whose playoffs have not kept up. The Jays are sinking further and further into sub-mediocrity in their shined-up stadium. The Leafs continue their Sisyphean existence: They push the stone to the playoffs and then watch it flatten them on the way back down the hill. The Raptors won, of course. But that and the high standards of the franchise are part of what has made their recent descent so jarring. They’re not just supposed to be better than this, they were.

When faced with a losing team or a bumbling franchise, the natural temptation is to look for solutions. Fire the coach! Fire the GM! Put the owner on an ice floe and push it out to sea! Toronto has tried these solutions before, or at least, most of them. It has only occasionally worked out.

Solutions aren’t simple. There is no one easy throughline that binds the Leafs, Raptors and Blue Jays and their current situations. Yes, this is a city where pro sports are mined for money, and has been forever, and that’s clearly the underlying purpose of both MLSE and the Rogers-owned Jays. Return on investment rules in this town.

That might explain the Jays, at least, who live in a bigger city than they seem to acknowledge. When times are good for the Jays, it’s like a vast underground aquifer gushes forth during a drought. The 2015 team was watched by nearly a million people a night during the regular season and was pulling in four million to five million TV viewers a night in the playoffs. Jays games were three of the eight highest-rated broadcasts in Canada that year, and the team led the American League in attendance in 2016 and 2017.

By 2019, attendance was nearly cut in half from that 2016 peak. Even this year, the Jays are third in the AL in attendance: It’s a hangover from the last two playoff seasons, in a park that, after its $400-million renovation, seems as geared toward producing hangovers as anything else. But season-ticket renewals have been moved to before the 2024 trade deadline, which seems ominous.

The Jays are what the Raptors are still becoming: a true national brand with roots that burrow deep across the country, but can sit idle, too. There’s money to be made with smarts and real ambition, big ambition, but there’s more. There is success waiting. In a gladiatorial division, you have to be something. If Toronto can’t be as developmentally focused as the Rays — and more or less nobody in baseball has been able to match Tampa Bay’s rags-to-riches system — or now the Orioles, then they have to aim higher in other areas. Their reach shouldn’t exceed their grasp.

“If we win — when we win — I believe that we can be a Goliath on par with the Bostons, the Chicagos, the Anaheims,” then-GM Alex Anthopoulos said in 2010. “We can be there. We have the ownership, we have the market size, we have the city and country to draw from.

“I had a journalist come to spring training from ‘Le Soleil’ in Quebec City, and I said, ‘You remember where you were when Joe Carter hit that home run?’ And he said, ‘Absolutely. I remember exactly where I was.’ And that’s a guy in Quebec City. And when we signed Adam Loewen, from British Columbia, he remembered where he was. And it just shows you the power this team can have if it wins, when it wins. If it’s a contending team year in and year out, it can captivate the country. Is it easy to do? Absolutely not, especially with the division and the teams that we’re competing with. But can it be done? 100 per cent”

Anthopoulos, of course, built those 2015 Jays by squirrelling away budgeted money to make deadline deals without having to ask ownership for more cash. Under Rogers, the Jays just don’t do truly big ambition, not since 1993. They’re financially outmatched by the richer teams in the division, and aren’t as smart as the smart ones. And hiring management that reflects the corporate small-to-mediumball mentality of Rogers ownership has, in the past decade, produced small-to-mediumball results. It’s a corporate team, in a corporate town. Mediocrity is almost a birthright.

So is Toronto’s sports problem a lack of ambition? From the time he arrived here, Ujiri would exhort the city: Stop thinking you’re too small, too out of the way, too Canadian, too doomed. He sure believed this city thought it was smaller than it was.

“The narrative of not wanting to come to this city is gone,” Ujiri said at the beginning of the 2018-19 season, after trading for Kawhi Leonard. “I think that’s old, and we should move past that. Believe in this city, believe in yourself.”

Ujiri was driven by a fire that propelled him from the couches of acquaintances as an unpaid scout to being the first African-born president of any North American sports team. As his charitable organization Giants of Africa always says, he dreams big. 

Of course, once the Raptors won, things went wrong. Ujiri’s Raptors trusted they could make trades if they needed to, could teach players to shoot threes, could unearth talent where others missed it, because all that had happened before. It hasn’t worked out that way.

At least the Raptors lived up to what this city should be, and only sometimes is: a truly world-class place. After the title, Ujiri’s strategy of waiting for another star to spring free was still ambitious. But Giannis Antetokounmpo stayed in Milwaukee after winning a title, Kevin Durant chose to play with Devin Booker, Damian Lillard chose to play with Giannis, and the Raptors were left with assets that didn’t fetch anything close.

But the Raptors won the city’s first major sports championship since 1993, and flags fly forever. Maybe true ambition is the key to success in Toronto.

Except Shanahan had ambition, too.

“Being born in Toronto does not necessarily make you a good executive with the Toronto Maple Leafs,” he said in 2014, after he was named president. “But this … was a very personal decision. This, to me, would mean more than anything I was able to accomplish as a player, because I am so emotionally invested in this place.”

The contract he gave Mike Babcock broke records; luring Lou Lamoriello from the Devils was no small swing. Poaching Kyle Dubas and Mark Hunter from junior hockey, building out one of the most enormous front offices in sports — both Shanahan and Ujiri were given significant resources by MLSE — and trying to fix the Leafs was not an act of safe sports planning.

Shanahan just didn’t hit on the right formula. The dominant joke about the Leafs — “plan the parade” — is old enough to have gotten rich on a primary residence by now. The Shanahan era produced just enough success to make the failure not just unprecedented, but crushing, and borderline cursed.

If a Cup champion like Ryan O’Reilly was telling friends it was too much of a country club, well, maybe it was. If a decent chunk of players prefer the Goldilocks medium of an American city that cares enough about hockey but not too much, then Toronto is not so much a hockey Mecca as a hockey hot stove. It’s too hot for some people to touch.

And if Mitch Marner can go from a joyful terror to a resentful object of trade speculation — or extension speculation, since the Leafs have little trade leverage anyway — maybe this is a tough market, for some. Then-assistant Paul MacLean was talking about the demons that haunted these Leafs in 2021 after losing just four playoff series, three as the underdog, and three of which came in the deciding game. So 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 Marner and William Nylander and John Tavares and Morgan Rielly proclaim not to be haunted by five-and-a-half decades of failure, it’s the last decade of failure that belongs to them.

And really, the weight only increases, especially for the Leafs. Mats Sundin once said that once he relinquished the captaincy of the Leafs, once he was truly out, he almost existentially exhaled. The pressure, he said, was real.

So the Leafs relied on their stars. The list of star forwards who have won Cups gets longer almost every year: Jonathan Toews and Patrick Kane, Sidney Crosby and Evgeni Malkin, Alexander Ovechkin and Evgeny Kuznetsov and Nick Backstrom, Nikita Kucherov and Steven Stamkos, Nathan MacKinnon and Mikko Rantanen, even Jack Eichel. And this year, Aleksander Barkov and Matthew Tkachuk and Sam Reinhart.

And if you want to argue that Shanahan should have been given less rope, you could point to the fact that after Leiweke, the CEO was placeholder Michael Friisdahl, who was more of a money man than a man of influence. If you want to argue the rise in franchise value provided a lack of organizational urgency, sure.

But after years of impatience, Toronto’s defining sports organization approached the game with a steady hand, with resources commensurate with the city they live in, and with a core of stellar forwards, some of them even local boys, and they have still managed to fail in an entirely new way in this town.

The Leafs have become a crew who both carry and create their own oceanic weight, playing out in the biggest media spotlight in the country, in front of a crowd that may be the worst crowd in hockey, in a town that so desperately wishes it could experience that hockey happiness, just once. It’s been a while.

Which is why you need the right guys, and the Leafs thought they finally had them. They were wrong.

Maybe that’s the simple, expansive, correct throughline: you need the right guys. (Or in the executive or coaching ranks, as sports move forward, the right women.)

The Jays had Anthopoulos in the GM chair and let him go, and after executive finishing school with the L.A. Dodgers he has become exactly the general manager the Jays could use: brilliant, swashbuckling, ambitious as hell. Toronto’s corporate middle managers pale in comparison.

The Raptors, meanwhile, tried to put Barnes with Pascal Siakam, Fred VanVleet and OG Anunoby, but the mix was the wrong one thanks to personality, contract status, history and fit. Whether Barnes is a true superstar cornerstone is now the most relevant question.

As for Shanahan and the departed GM Dubas, or current GM Brad Treliving and coach Craig Berube, or the core four of Matthews, Marner, Nylander and Tavares, you can decide which are the wrong guys. But if Connor McDavid was a Leaf instead of Matthews, for example, it all would have changed.

Shanahan had to know his players better than anybody and make the call as to whether they were the right ones for the job. He had the wrong guys, and should have known. Maybe running it back with some adjustments will work better, sure.

One day, the Leafs will win another Cup. One day, the Raptors will rise again. One day the Jays may overcome their corporate mediocrity. It’s all possible.

The city will be ready, when it does.