How Kawhi’s Game Winner Affects the Toronto Maple Leafs

TORONTO, ON - MAY 12: Toronto Raptors forward Kawhi Leonard (2) celebrates after his shot drops for Raptors to win. Toronto Raptors vs Philadelphia 76ers in2nd half action of Round 2, Game 7 of NBA playoff play at Scotiabank Arena. . Toronto Star/Rick Madonik (Rick Madonik/Toronto Star via Getty Images)
TORONTO, ON - MAY 12: Toronto Raptors forward Kawhi Leonard (2) celebrates after his shot drops for Raptors to win. Toronto Raptors vs Philadelphia 76ers in2nd half action of Round 2, Game 7 of NBA playoff play at Scotiabank Arena. . Toronto Star/Rick Madonik (Rick Madonik/Toronto Star via Getty Images) /

Kawhi Leonard converted the biggest shot in Toronto Raptors’ history, a moment that the Toronto Maple Leafs have yet to achieve in this generation.

With the Toronto Maple Leafs’ 2018-19 season well behind in the rear view mirror, I have been keeping a close eye on their arena roommate in the Raptors on their playoff run. By no means can I consider myself a die-hard basketball fan, but I have enjoyed this current run nonetheless.

On Sunday night, I attended the tailgate party outside Scotiabank Arena with some friends to watch Game 7 of the second round matchup between the Raptors and Philadelphia 76ers. It was an incredible spectacle to watch from start to finish, seeing the energy inside and out of the arena and the tight game between two competitive teams.

So, it was not too surprising to see that the game and series would need to be decided in the closing seconds and the score so close. The Raptors knew the only person they wanted to take the last shot was Kawhi Leonard and he delivered with the most the craziest and most important shot in franchise history.

In an instant, my friends and I, as well as everyone in the square, lost our collective minds over how Kawhi was able to pull it off. I instantly knew that this moment would be right up there with the likes of Jose Bautista’s bat-flip as a generation-defining moment for Toronto sports.

Which brings us back to the Leafs, whom I believe have yet to achieve such a moment with their current core for this generation of fans. It hasn’t happened for quite a long time and one that I long for even more after Kawhi’s memorable shot.

Some Special Moments, but None Long Lasting

The Leafs have been on the upswing for the past few seasons and are most certainly trending in the right direction towards their goal of doing the thing. At the same time, they are playing second fiddle in the city’s sports landscape to the Raptors, who deservedly hold the title of Toronto’s top dog in sports.

It shows up in spades when it comes to memorable moments in recent Toronto sports history, with the Blue Jays and TFC so far ahead of the Leafs in this department, as well.

Aside from Bautista’s iconic home-run, Edwin Encarnacion’s walk-off homer in the 2016 Wild Card Game is most definitely on that list. You could also add TFC winning the city’s first pro title of this millennium to the list as well. Even the entire 7th inning leading up to Bautista’s dinger is an iconic Toronto sports moment.

Don’t forget about the other teams in the city achieving success, including the Argonauts in 2017, the Marlies last year (and potentially again this year), and the Wolfpack. They may not be generation-defining moments, but they are still successes nonetheless.

So what about the Leafs; what has been their defining moment for this new generation? To put it simply, they haven’t achieved it yet.

Auston Matthews’ historic debut is most certainly memorable, but it was merely a great game in the regular season. The same goes for his OT goal in the 2017 Centennial ClassicKasperi Kapanen’s and Tyler Bozak’s OT winning goals against the Washington Capitals were jaw-dropping, but they ultimately didn’t amount to anything since the Leafs didn’t advance.

Frederik Andersen pulled off an impressive save in Game 3 against the Boston Bruins last year, but it was also merely a footnote in a series that ended in disappointment. John Tavares signing with his hometown team was a shocking story when the news broke, but it was soon overshadowed by the Kawhi trade just a few weeks later.

Even this season, the only moments that will stand out for Leafs fans will be Mitch Marner’s penalty shot goal in Game 1 and Matthews critical goal in Game 5 against the Bruins. That’s because, yet again, these moments were all for nought, since the Leafs lost in another Game 7.

While it is unfair to criticize a young team who will soon be heading into their fourth season together as a core for not yet having a generation-defining moment, you can’t help but wonder when it will be the Leafs turn to achieve one. Because once they do, all of the aforementioned moments in recent franchise history will take a back seat to this hypothetical moment.

The Leafs Haven’t Had Such a Moment in Years

If you really think about it, when was the last time the Leafs have had a moment akin to Kawhi’s game-winning shot? Let’s not beat around the bush, it’s been quite a long time since the Leafs have had a generation-defining moment.

The first two that immediately come to mind for me are Nikolai Borschevsky’s OT winner against the Detroit Red Wings and Doug Gilmour’s OT winner against the St. Louis Blues in 1993. I also think of Garry Valk’s series-clinching goal against the Pittsburgh Penguins in 1999, and the countless moments from Mats Sundin.

But therein lies the problem. For me to remember a generation-defining moment for the Leafs, I had to think back to previous eras of Leafs hockey, some that occurred well before I was born. The fact that the last such moment happened at an age where I couldn’t fully remember or appreciate it is saddening to me. I can imagine that I am not alone in this thinking.

A lot of this can be chalked up to the Leafs being bad and unmemorable for nearly a decade, especially with a prolonged playoff slump to go with it. Add to the fact that the last time the Leafs advanced past the first round was in 2004, it’s no wonder the team has left a generation of fans desperate for a moment to call their own.

Going back to the Raptors, this Kawhi shot was a long time coming for the team and their fans after years of disappointments and shortcomings. Prior to Sunday’s memorable win, the Raptors had only made it to the Eastern Conference Finals once in their 5 seasons of contention.

Additionally, the most iconic moment for the franchise was one of failure with Vince Carter missing the game-winning shot against the same 76ers in 2001. It’s now been replaced by one with a happier ending and is one that many sports fans will gravitate towards when they think of the Raptors.

Regardless of how much further the team goes in the 2019 playoffs, Raptors fans can at least rest knowing that the future of the franchise is brighter than ever before. They have achieved new heights and the team has cemented themselves as the city’s top-dog in terms of Toronto sports.

By no means does this mean all hope is lost for the Leafs of this generation. As mentioned earlier, the current core is still in its early stages and have a lot of mileage left in the tank.

Instead, Kawhi’s clutch moment was one that the Leafs can learn a lot from as they continue to grow. It took this current iteration of the Raptors six seasons to achieve such a generation-defining highlight, and also reach the heights fans of the team had longed for.

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It often takes years of heartbreaks and adversity in the playoffs for a team to figure it out and finally pull it off. Staying the course and remaining focused on accomplishing the goal of clinching a title by any means necessary is vital for any teams long-term success.

The Raptors got their generation-defining moment last night and are now one step closer to winning their first ever championship. For now, the Leafs will have to wait their turn to achieve the same thing.