The Toronto Maple Leafs have been able to turn their fortunes around immensely over the past 5 years from league cellar dweller in 2015 and 2016 to surprise playoff team in 2017 and Cup contender in 2018 and 2019. This has been possible through the drafting of forwards William Nylander, Mitch Marner, and Auston Matthews in the 2014, 2015, and 2016 NHL Drafts, the trade for goaltender Frederik Andersen in the summer of 2016, and the free-agent signing of superstar forward John Tavares in the summer of 2018, amongst other moves that the Leafs made. But with first-round playoff losses each of the last three seasons, amongst other reasons, there is increasing pressure on the blue and white to make a deep playoff run.

The Leafs looked like they were going to win their first playoff series since 2004 this year against the Boston Bruins, as they had series leads of 1-0, 2-1, and 3-2, but were unable to win that fourth game in Games 6 or 7, meaning their season would be ended by Boston for the second straight year. Part of this loss could be attributed to forward Nazem Kadri's season ending suspension in Game 2 of the series, resulting in less depth for head coach Mike Babcock's team. The early playoff exit and Kadri suspension led to general manager Kyle Dubas making a big move this offseason.

Needing to booster the defense core, Dubas traded Kadri and young defenseman Calle Rosen to the Colorado Avalanche for premier offensive defenseman Tyson Barrie and third line forward Alexander Kerfoot. The Avalanche retained salary on Barrie's contract, meaning the Leafs will only have $2.7 million going against the salary cap for Barrie, quite a steal. Even with this move, along with the trade for defenseman Cody Ceci, there are reasons that make the 2019-20 season incredibly important for the Leafs franchise.

Barrie, along with other Leafs defensemen Ceci, Jake Muzzin, Travis Dermott, and Ben Harpur are all going to be free agents of some sort in 2020. Barrie ($5.5 million), Ceci ($4.5 million), Muzzin ($4 million), and Dermott ($863k) will all be looking for raises in free agency, meaning the Leafs may not be able to keep all of them. With so many key defensemen in contract years, especially with Barrie rumored to be a one year rental for Toronto, this puts pressure on the team to make a deep playoff run now.

Another point of pressure on the Leafs is the fact that they are the center of attention in hockey circles much of the time, they have not won a playoff series in so long, and have so much talent on their roster currently. Toronto is a hockey-crazed market, as it is the biggest city in Canada, meaning that the franchise has attention on it 24/7 from the Canadian sports media, Leafs fans, as well as other hockey fans who want to see them fail. As mentioned before, the Leafs haven't won a series in 15 years and haven't won a Stanley Cup since 1967, the longest Cup drought of all of the Original Six NHL franchises.

With talented players such as Matthews, Tavares, Marner (presuming he signs a contract with the Leafs during the offseason), Morgan Rielly, Andersen, Barrie, and Muzzin, there is clearly potential for the Leafs to win a Cup. Despite the fact that they will be formidable for the next 3-5 years at least, with the free agents upcoming next summer, the pressure from media and fans alike, and the failures they've had the past two seasons to beat Boston, the Toronto Maple Leafs must make serious noise in the 2020 Stanley Cup Playoffs.