Who has it worse: Pre or post-2000s Leafs fans?

Photo credit:Nick Turchiaro-USA TODAY Sports
Alex Hobson
7 months ago
It’s no secret to anybody that we’re in the dog days of summer at this point. Outside of the outliers like the contract extensions for Auston Matthews and Sheldon Keefe, there’s usually next to nothing to talk about around late August to early September. Training camp is still a few weeks away, although quickly approaching. 
You’re probably thinking that the discussion around those things has been beaten into the ground already, so today we’re going to take a look at something different. The type of thing that we’re probably not talking about in the middle of November or January. It’s a question I’ve mulled over with myself a number of times before; Who has it worse between the pre-2000s fans or the post-2000 fans? 
Before we make a case for either side, let me explain my logic for choosing that range to divide the fans. It’s pretty simple; that’s the last time the Leafs had any legitimate success. No, they didn’t win any Stanley Cups, but they gave the fans plenty to cheer about in comparison to what they got from the time that passed between John Ferguson Jr. and Lou Lamoriello. A Conference Final appearance is something the team hasn’t had since 2002. 
To put things into context – I’m 23 years old. I started watching the team in 2005 when I was six years old. My first season paying any attention to the NHL was the year after the lockout, 2005-06, and the 2006-07 season was when I fell in love with the team and the sport. To further this context, the year I started watching the team was the year they began a seven-year playoff drought that lasted until the shortened 2013 season. Can somebody remind me what happened that year? 
To kick off the ten years that have passed since that lone playoff appearance and subsequent collapse, the Leafs missed the playoffs the first three years in a row and then decided one drought wasn’t enough. Despite a new era filled with hope and newfound expectations, they failed to win a round for the next six years before finally slaying the dragon against the Tampa Bay Lightning in 2022-23. 
To summarize, in the 18 years I’ve been a fan of this team, they’ve missed the playoffs a total of 11 times (if you’re including the 2019-20 tournament in the bubble), and failed to win more than a round in six of the seven years they did make the playoffs. If you follow the team closely enough that you’re invested enough to come back every year, then you didn’t need me to remind you of all that, and for that, I apologize. 
If it’s not obvious by this point, I’m of the belief that the fans who either weren’t alive or weren’t old enough to remember the glory days of the early 2000s have it worse than the ones who do. This is obviously a biased opinion, and I can easily understand why older fans would disagree with me. 
The reason this debate is alive comes down to one question in the end. Does having witnessed your favourite team have success make things worse in the present? Or does it have no effect? 
While I do think fans like myself have it worse, there’s a good case to be made for the other side too. Whether it was something that took place during your childhood or something you had to wait until you were an adult for, the opportunity to witness events like Stumpy Thomas’ overtime winner against Ottawa in Game 5 of the 2000 first round was welcomed. Or how about Mats Sundin’s overtime winner against the Senators the following year? Even though they didn’t win the game, Sundin’s last-second goal to tie the game against the Carolina Hurricanes in the first game of the 2002 Conference Final always brings back good memories when I bring it up to fans who watched it happen. 
And hell, just for pure entertainment purposes, the post-2000s fans never got to see Tie Domi fight a fan in the penalty box. 
Sure, you can laugh at the fact that the “glory days” of the early 2000s are composed of a couple of Semi-final appearances and a Conference Final, but considering the impending drought of pain that was about to come, this, to me, would have been paradise in comparison. 
So, that brings us back to the question. Does carrying those fond memories make things worth it for the older crowd? Does it make it harder to watch when the Leafs are stunned by a hot goalie in a playoff game where they desperately need offence because they remember what the team was once capable of? Are the younger fans better off not having those memories of success? If you ask the 90s babies and beyond, the answer is probably yes. 
But I’m not so sure. 
If you ask me, I’d be grateful to have more joy than less joy. While that John Tavares series winner in Game 6 overtime this past season brought me enough to last a lifetime, after that it fizzles out pretty quickly. The overtime-winning goal from Auston Matthews in Game 4 against Columbus was great, as were the respective overtime winners from Kasperi Kapanen and Tyler Bozak in Games 2 and 3 against Washington, but I feel like there’s still a massive gap. 
On the other hand, I can’t definitively say I’m better off in the year 2023. I was still learning to speak and walk in the front half of the 2000s, so how would I know for sure that I’ve got it harder because I don’t have those memories? Maybe the feeling of dread that comes with every playoff run would be even harder to take in the end than it already is for me. 
It’s one of the more subjective questions there is. 
In the end, we can all agree that this franchise has put its fans through a serious gauntlet of pain in the past 20 or so years. That’s the only reason I ever think about this question anyway. For as much as I think my take is justified, I have serious empathy for the ones who have been a fan for even longer than I have. Because let’s be honest – the struggles of being a Leafs fan didn’t just begin in the mid-2000s. The 1980s provided its own kind of pain, and in the end, this team hasn’t won a cup in nearly 60 years. Disgruntled feelings are justified for every Leafs fan, no matter when they started watching. 

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