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Summer Series: The Defining Moments of the Toronto Maple Leafs Since the 2000s

August 3, 2025 by Last Word On Hockey

Hockey, and sports in general, can be broken down into moments. Some moments are bigger than others and chart the course of a franchise and an entire league. These moments can define a team’s destiny for years to come. For this installment, we bring you the defining moments of the Toronto Maple Leafs in recent history. This follows yesterday’s full history defining moments, but now it is time to discuss the more recent defining moments. So, let’s get into it. 

The Leafs Win the Draft Lottery in 2016

The late 2000s and early 2010s were a tough time to be a Leafs fan. The team was bad. Really bad. And it did not look like they were set to get better. The Leafs only made the playoffs once in a decade span, between 2005-06 and 2015-16.

The Run Up

In 2016, the Leafs were starting to piece together a team that could have a future. The team had just brought in head coach Mike Babcock and general manager Lou Lamoriello, both of whom were big gets for a struggling franchise. They had drafted William Nylander and Mitch Marner, with Morgan Rielly emerging as a good piece on the blueline. However, as promising as it was, they still lacked that piece that was game-altering. Nylander and Marner were both fantastic prospects, but the team needed an unquestionable force.

With the Leafs allowing their prospects to develop in their respective junior leagues and the AHL, the roster they were icing on a nightly basis was less than ideal. Their top goal scorer was P.A. Parenteau, and their All-Star representative was Leo Komarov, to put the quality of the roster in reference. This performance saw the Leafs finish last place in the NHL.

The Moment

On April 30th, 2016, the Leafs got the direction they were hoping for by winning the NHL Draft Lottery. And on June 24th, they sealed it. The Leafs selected Auston Matthews first overall in the 2016 NHL Entry Draft.

The Aftermath

In the immediate aftermath, Auston Matthews missed out on the Leafs rookie tournament because he was named to Team North America in the 2016 World Cup of Hockey. In this tournament, he posted two goals and an assist for three points in three games. Furthermore, he followed this up by scoring four goals in his first-ever NHL game. Auston Matthews was looking to be everything the Leafs wanted and needed. He proceeded to score 40 goals in his first year on route to winning the Calder Trophy and leading the Leafs back to the playoffs.

Since then, Matthews’ individual accolades include three Rocket Richard Trophies, a Hart Memorial Trophy, and a Ted Lindsay award. He has both a 60 and a 69-goal season, the latter is the most scored in a single year since Mario Lemieux in 1995-96.

This decision has defined the Leafs for the past decade. While they haven’t had the playoff success that one would have hoped for back in 2016, there’s no denying Matthews’ capabilities and how it has shaped the Leafs on and off the ice. He is the strongest goal scorer in the NHL, the captain of the roster, and the face of the franchise.

Other Recent Defining Moments

Tavares Is Coming Home

Another one from this era, John Tavares signing with the Leafs was a monumental occasion. Tavares was the biggest free agent to hit the open market in the salary cap era. It was long just assumed by many that he would wind up re-signing with the team that drafted him, as most star players do. Like Steven Stamkos before him, players at their peak never would leave in free agency. However, that all changed with Tavares. He came home!

It marked a new era for the Leafs. One where players wanted to come play here. A place they thought they could win and be a part of something bigger. Not a spot where they get traded and have to show up because their contract said they had to, and would request a trade instantly. As much as drafting Matthews or bringing in Babcock could be argued to have had the same effect, it was Tavares leaving his old team and coming home that communicated that to the rest of the hockey world.

Meltdown in Beantown

There is no moment in recent history more synonymous with the Leafs than losing to Boston in Game 7. It was 4 to 1. With a little over 11 minutes to go in Game 7 of the first round of the Stanley Cup Playoffs, the Leafs were leading the Bruins 4-1. The Leafs had been down 3-1 earlier in the series. It looked like we were going to see an incredible comeback. What we got instead was an incredible comeback. The Bruins became an unrelenting force. A goal by Nathan Horton started it all. Then Milan Lucic netted one. Next, Patrice Bergeron forced it to overtime with less than a minute left. And, of course, Patrice Bergeron again in overtime.

This moment didn’t change the direction of the Leafs franchise in any way. They were already lucky to have made the playoffs that season. The roster wasn’t overly strong. It didn’t force a rebuild that wasn’t already due to happen. But it perfectly sums up what it was like to be a Leafs fan in this era. It defined that era as constant heartbreak.

Main Photo Credit: Dan Hamilton-Imagn Images

The post Summer Series: The Defining Moments of the Toronto Maple Leafs Since the 2000s appeared first on Last Word On Hockey.

Filed Under: Maple Leafs

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