think of supporting a team like a car manufacturer trying to get a customer into an entry level vehicle.
The leafs have pretty much lost a generation of potential fans by being horrible for the last 8-10 years. A lot of those young fans cannot be salvaged as they've made commitments to teams like Chicago, L.A, Pittsburgh etc. As they grow older, they become less impressionable and less likely to be swayed back into leaf land.
Car manufacturers do the same. Come in where you're 19 and buy a Chevy Cavalier. Hopefully you buy an impala in a handful of years from now, then a lincoln truck and hopefully a corvette on the side. Banks want you to open a student savings account early. They really want that mortgage from you in 10-15 years.
Once people gravitate to something, it's hard to steer them off. The same can be said for supporting a sports franchise. People will commit to a sports franchise if they're good and support them when they're bad but the team has to be good in order for a new hockey fan to show interest in that team. You don't see too many kids that are flordia panther fans in toronto (I imagine there's more tampa bay fans....and more to come of them).
Another case and point is the late 70's in baseball. The Jays came into the league and obviously weren't very good. The Yankees, at the time, were great. A lot of the kids born in the mid to late 60's (in toronto and many other cities) became Yankee fans. Even with the introduction of a Toronto team, those fans already pledged their allegiance. All this is not good for leafs. Not at all.
A personal example is: during the late 80's and very early 90's, I was young and a Calgary flame fan. If it weren't for Dougie G for those few years and that team he brought with him, I would have been stuck and committed to the calgary flames (haha). I was sucked into leafland because I was from Toronto but more importantly the leafs had a very good and very likeable team. That happened at a time where I was young and impressionable still. Had that happened a few years later in life, I highly doubt I would have ever become a leaf fan.
Lastly, a few people made the point about misery sells in media. That is 100% correct - however, it can only sell for a certain amount of time. If you don't think the leafs aren't losing their fanbase, you're wrong. The opportunity cost of being terrible for so long is: they lose the commitment of potential new "beleafers". Misery does sell, as long as the story engages the viewer/reader. The viewer/reader has to have an emotional connection and has to relate to the story. Case and point, blockbuster video. During it's demise, it was the talk of the town. The public and the news was worried about video stores and their demise. It was such a big issue. Will these other sources fill the gap of what blockbuster provided? Blockbuster was such a staple in people's lives. Looking back years later, blockbuster was replaced and almost forgotten by better choices. During their demise, they got tons of publicity and public concern. Now they're just a memory.
All this does not bode well for the leafs. If they refuse to rebuild and continue on this current path, they will lose another generation of potential fans - fans that pledge their allegiance and then become deeply engrained into that team without turning back. A rebuild provides hope and potential. The current path is doomed for the squad as well as for entry level fans. MLSE better smarten up. Brand loyalty only exists to those who are already committed.
Not a surprise that the Leafs are a disaster, with poor customer service like that.
