This profit-making move tapped into the Toronto rich. It changed the games for Leafs, Raptors and now the Blue Jays

Is that success? Or is it enough failure to really matter? Again, the on-ice product is only part of the answer. For all their playoff pratfalls, Forbes said the Leafs were worth $1.33 billion (U.S.) when Shanahan signed on, tops in the league. Earlier this season, Forbes put that theoretical price tag at a whopping $2.8 billion (U.S.). The Leafs are still No. 1 at something.

So while it’s clear that if hockey legends have historically been made in the playoffs, the NHL’s most lucrative empire most certainly has not. Yes, newly installed CEO Keith Pelley insisted the Leafs want to win — “We’re not here to sell jerseys,” was the money quote from Pelley’s first public press conference as MLSE’s leader — but Pelley works for the club’s consortium of owners, and an owner’s bottom line is enterprise value.

And on that front, the Leafs lead the league, and the Raptors lead the nation. Forbes had Toronto’s NBA team pegged at $520 million (U.S.) in 2014, one year into the Masai Ujiri era, and after a run of franchise-defining success and a few rougher years the Raptors are now worth an estimated $4.1 billion (U.S.). Add those two franchises alone, and before things like expenses and inflation, and despite the impact of COVID, the gross annual increase in franchise value, before a ticket or a jersey has been sold, has been over half a billion U.S. dollars per year.

And while nobody would say the increase in franchise value is what is keeping a Shanahan in his chair, it’s at least part of the calculus: reducing urgency, mollifying consequences, expanding what constitutes franchise success. The twin telecom giants who own the Leafs and Raptors could make more money with more playoff rounds, sure. But while the Leafs may have the longest Stanley Cup drought in hockey history and a dispiriting playoff record, they are following tradition in this town by making sure Leafs owners win at the bank. Toronto’s Core Four, too, have demonstrated the same idea: you don’t need to be a Cup-hoisting legend to get insanely rich off the game.

It’s been thus through the ages. No amount of futility, post-season or otherwise, has ever threatened the fiscal prosperity of the Leafs. Even in the dark days of miserly Harold Ballard’s run as owner, when the Leafs fell into competitive irrelevance in the 1980s, the team still played to full houses. Maple Leaf Gardens was still known as the Carlton Street Cashbox.

“I don’t think he gave a s—- about the team, I really don’t,” Rick Vaive, the three-time 50-goal scorer for the Leafs in the 1980s, once said of Ballard. “All he cared about was having people in the seats and making money.”

That profit motive was almost literally built into what is now known as Scotiabank Arena, too. There were always people in the seats — that’s a Leafs-specific phenomenon, in a country where other NHL teams can see empty seats in tougher times. Toronto is Canada’s richest city by a wide margin — it is estimated that 20 per cent of Canada’s GDP is generated by the Big Smoke — and the Leafs, as the city’s original sporting cash cow, have made an art of digging into Toronto’s collective pockets, starting with its wealthiest citizens. Richard Peddie, CEO of Maple Leaf Sports &  Entertainment from 1998 to 2011, remembers looking through a book that detailed the earliest season-ticket holders at the Gardens, which opened in 1931. The names on the ledger were the blue bloods of old-money Toronto: families such as the Eatons, who owned the famed department store, and law firms such as Torys, which came to own dozens of seats.

For all that, Peddie said that in the waning days of their Gardens residency the Leafs were leaving money on the table.

“I described the Maple Leafs as ‘the company that time forgot,’” Peddie said. “They had no idea how to market, how to sell sponsorships … The whole food and beverage offering, I always said, was cold hot dogs, warm beer and stale popcorn. That’s what we sold. King Clancy’s ghost was still roaming around. It was still that way.”

In other words, the Leafs were profitable enough that they didn’t have to try very hard. When the Air Canada Centre opened in 1998, it was financed without the public subsidies commonly doled out to teams in other jurisdictions and that was laudable in the era of public stadium financing. But if taxpayers didn’t pay for it, somebody had to.

“Our owners paid the full ticket,” Peddie said. “So our challenge as the business team was to generate revenues to ultimately get a payback.”

That explains an arena design that included premium restaurants and platinum seats with access to luxury lounges that Peddie still counts as a “brilliant” profit-printing move. Never mind that spectators who lingered over their shrimp and Chardonnay during intermissions have been leaving the lower bowl noticeably underpopulated at the beginning of periods ever since. Fans in the seats supporting the team was only part of the point, and part of the profit margin.

“I hated that fact that people wouldn’t come back to their seats, but there wasn’t much we could do about that. It’s, ‘Listen. I haven’t finished my bottle of Brunello in the lounge. I might just pass on the second period,’” Peddie said. “It’s very corporate. And the prices keep going up.”

The prices keep going up, in part, because the arena sits on Bay Street, steps from the headquarters of Canada’s largest banks and companies. That means on any given night plenty of the folks in the expensive seats are in attendance on the company dime for what amounts to a business meeting. Or they are people with money who aren’t afraid to spend it. A 2024 report ranked Toronto as the 13th wealthiest city on the planet with 106,400 millionaires among its residents, up 45 per cent over the past decade. Among the global top 50 in that ranking, Canada’s only other entrant was Vancouver at No. 31.

It’s remarkable, though: the effect of that corporate squeeze is a crowd that doesn’t come close to matching the fervour of, say, New York, which has even more money to burn. The Raptors, meanwhile, built a loyal fan base at less-than-the-Leafs prices but have been squeezing ever since, and the market is rich enough that it allowed Ujiri to justify an increase in ticket prices by approximately four per cent even in the wake of one of the worst seasons in franchise history.

“You feel for the fans sometimes … but this is how business works,” Ujiri said.

For a long time the Blue Jays were a reasonably priced major-league alternative, but that’s changing. It took a while for the Jays to follow MLSE, but the Jays didn’t spend $400 million to spruce up their ballpark to make the team better. Longtime season-ticket holders have complained about the prices of their tickets more than doubling, and if the sales pitch is to improve the venue by offering a selection of “premium clubs” for an “elevated experience,” the obvious goal is to do what the Leafs have been doing for years: maximizing their share of Toronto’s corporate entertainment dollar and household disposable income.

The difference is that packed houses for the Raptors and Jays aren’t unconditional. In Leafland, no amount of recurring playoff trauma seems to dull the appetite to pony up for another season, no matter the calls for change in the wake of another loss.

“The fans here not only deserve, but demand, a championship,” Pelley said last month.

If only the latter point were true. Maybe if it was — if Toronto’s hockey-loving populace was even capable of voting with its feet and putting pressure on ownership to truly try to win — the Leafs might have won a post-1967 championship by now, or hell, just played for a Cup. If Harold Ballard was solely focused on raking in cash over the performance of the team, then the past 20 years of MLSE have shown the company to be a moderated version of the same thing: ownership would like to win and is thrilled when a team like the Raptors pulls off the impossible, but the mountains of money generated by the operation help to cushion everybody when they fall.

After this past season, Shanahan said, “The results that we’ve had in the playoffs, our players know — we know, I know — they’re unacceptable.”

Unacceptable, for sure, but not unprofitable. That’s Toronto for you. The hockey team can break your heart by not even trying to win, or the hockey team can break your heart by trying its best and caving when it matters, and the only real through-line is this: in a city this rich, with a hockey team that occupies such a central spot in the lives and hearts and wallets of its citizens, it can’t ever truly fail.