"Why is Calgary such a tough market?"
This question has been put to a number of times over years. I've asked it myself. I have some theories, but first, let's set the table a little bit.
"Tough" in this formulation, doesn't mean "bad". As a hockey market, Calgary is anchored by sufficient grassroots interest and the kind of corporate density that fills luxury boxes. You can sell tickets and jerseys here.
But Calgary is certainly a tough media market. It is much more difficult to sell sports content in this town. Take it from someone who has launched, run, or written for multiple Flames-oriented entities over the years. The struggle is real. But why?
The simplest explanation can be expressed in a kind of formula: Population (size) X passion (fanaticism) = true market size.
Calgary maxes out at "medium" on both variables. It lacks the resolute fandom of, say, the Edmonton Oilers, and also the gravitational pull of a place the size of Toronto.
Edmonton is not a bigger market by population but boasts a deeper brand of fanship. Toronto is both ancient and enormous, relative to Calgary. Loyalty to the Leafs is generational, passed down as a birthright. Newcomers are also irrevocably sucked into the swirling maelstrom that is the totalizing Toronto Maple Leafs coverage - like light being absorbed by a black hole.
Calgary has neither of these qualities, at least not to the extent of the examples in question. There are two culprits from what I can see: the mistress effect and a lack of conversion events.
The Mistress Effect - There's a saying in Calgary that everyone here is actually from somewhere else. As a consistent net importer from the rest of Canada, many hockey fans arrive already married to another team. The Calgary Flames are a dalliance, a club seen on the side, the mistress team. It is not uncommon to hear competing chants at Flames home games.
Conversion Events - Fanship is built along several dimensions - proximity, norms, traditions, culture, etc. But a place and market like Calgary needs what I dub "conversion events", ie; winning in ways that galvanize and catalyze a fanbase. Cups build fans. Cinderella runs win hearts. Dynasties entrench generational affinity. These have not been totally absent in the organization's history, but they have been preciously rare.
Calgary's nemesis isn't the Edmonton Oilers or Vancouver Canucks. It's not any on-ice rival you can name. It's mediocrity. The Flames franchise has been running from it in earnest since the great extinction event that saw their stars depart for greener pastures in the 1990's. And like an immortal antagonist from a classic slasher flick, mediocrity always seems to catch up to the Flames just as they are on the edge of escape.
The club's "conversion events" have been intermittent at best for the better part of three decades. Since the turn of the century, you can count them on one hand - the 2004 cup run (lost in the finals), the 2014 surprise playoff berth (lost in the second round), and the recent 2022 first-round OT win (lost in the second round). If you're generous, you can also mark finishing atop the 2019 Western Conference (lost in first round). These, of course, are rather soft examples since there's no sustained success, no ultimate victories. But it's what we got.
The Flames have only appeared in the Stanley Cup finals three times in their history, with two occurring in relatively rapid succession back in the day (1986, loss to Montreal, 1989 win over Montreal). Their spin at the top of the league during that period was the closest the franchise has come to a dynasty, and likely remains a primary source of core, generational fanship culture here. Unfortunately, it was cut short by a series of gut-punch playoff losses in the early 90's (Los Angeles Kings, Edmonton Oilers, Vancouver Canucks, San Jose Sharks).
The "Young Guns" era that followed was a period of not just failure but despair, and the only existential threat the organization has ever faced. Irrelevancy and embarrassment, nearly a decade long, it was eventually halted by the emergence of Jarome Iginla and the arrival of Darryl Sutter. If you ask ownership now, you'd find that this is the boogeyman they seemingly flee from - not just mediocrity, but hopelessness and humiliation. The doldrums between 1996 and 2003 left an indelible mark on the psyches of those involved and upon the collective consciousness of the market as a whole.
If you ever wonder why the team is loath to consciously rebuild, simply peruse some of the hapless rosters of that era.
The impact of key conversion events can be illustrated by the 2004 Cinderella run. The Flames went from a punchline to inspiration. The Red Mile and its exuberance was a kind of Cambrian explosion of fanship. If you ask almost any Flames fan of a certain age, they will trace their initiation to the fanbase back to 2004 (18 years in the rearview mirror at the time of writing).
So the next question is - will Calgary ever hit a kind of escape velocity as a sports (content) market? It certainly seems this club's fate is to vacillate between very good and kind of bad indefinitely. The organization has skirted sustained greatness and outright despair once each over its history but mostly avoids both. Calgary has reached the Western Conference final once since its cup win in 1989. It has also never picked any higher than 4th overall.
With Brad Treliving's handiwork this off-season and Sutter remaining a the helm, the Flames will again be a going concern in the West. They probably won't be the best team in the league, but they certainly won't be the worst. While it is difficult to predict exactly how things will evolve over the coming months, it will almost likely end up seeming eerily familiar for Calgary fans.
As for that implacable foe, that interminable habit of pushing desperately away from the worst only to fall short of being the best - the club may eventually find that the only way out is through.