What’s the most entertaining playoff run possible for the Toronto Maple Leafs?

With the playoff bracket set, the picture for what teams will have to go through to claim Lord Stanley’s Cup becomes a bit more clear. There are no easy paths in the playoffs, so trying to figure out an ideal gauntlet of opponents for the best odds at winning it all would be a losing battle. Instead we ask, what’s the most entertaining playoff run possible for Toronto and its fans?

“The most entertaining run is the one where they win it!”

Yes. Obviously. We’re all well aware of that being the end goal. But not all wins are created equal, some are a bit more fun, others a bit more chaotic.

The Revenge Tour

The Path: Ottawa – Florida – Montreal – Los Angeles

Starting it off with one that would certainly cause the Maple Leafs’ fanbase to make all the previous times they were called obnoxious look like a humble debate in comparison. The Revenge Tour sees Toronto knock off its provincial rival, then take down the three franchises not named Boston who have caused it the most pain in both recent and long-term memory. 

The second round loss to Florida from two seasons ago gets its rematch, followed by slaying the demons of blowing a 3-1 lead against Montreal. Last, Toronto gets to finally face the ghosts of the 1993 Conference Finals when Wayne Gretzky’s missed high-stick on Doug Gilmour helped Los Angeles defeat Toronto.

The Journey Through Canada

The Path: Ottawa – Tampa Bay – Montreal – Edmonton

A playoff run that seems designed to sell those Toronto vs. Everybody shirts, and make the rest of the country hate its largest city even more.

After knocking off the nation’s capital, Toronto gets to face Tampa Bay, which is less of a city and more of a haven for retirees who are sick of shoveling driveways and pretending Tim Hortons has produced anything edible since 2014. The third round sees them take on Montreal in the sport’s most historic rivalry before giving Gary Bettman a brain aneurysm with an all-Canadian final against Edmonton.

The “Hey Coach!” 

The Path: Ottawa – Florida – New Jersey – St Louis

A weird thing about pro sports is your teammates one day and your most hated rivals the next. This playoff run would see Toronto go through some familiar faces behind the opponent’s benches.

We start off with Ottawa, coached by former Maple Leaf Travis Green before going against Paul Maurice’s Florida Panthers. Maurice spent two years coaching Toronto before being released despite a winning record while having Andrew Raycroft and Vesa Toskala in net. Up next is New Jersey, where Sheldon Keefe now calls the shots after being fired by Toronto last offseason.

The script flips in the finals where Toronto Maple Leafs head coach Craig Berube gets to face off against the St Louis Blues, his former team where he won a Stanley Cup in 2019. 

The Southern Hospitality

The Path: Ottawa – Florida – Carolina – Dallas

The recent political climate seems to have united Canadians more than ever before. But is it enough to make people from outside of Toronto cheer for the Maple Leafs? 

After moving past Ottawa, this path sees the Maple Leafs go through three of America’s red states, largely responsible for voting in the man who threatened to annex Canada and inspired countless acts of booing the American anthem from across the NHL. Should fanbases in Florida, North Carolina, or Texas start booing the Canadian anthem in return, will it be enough to get even fans in Quebec or Alberta cheering for the team that wears a Maple Leaf on their crest?

Only one way to find out.