Top 5 Toronto Maple Leafs Teams that Broke the Fans' Hearts

The Toronto Maple Leafs are like a sports bettor flush with cash who walks up to a book wanting to gamble big on the Super Bowl and doesn’t understand what the Moneyline means. The organization’s story is a tragedy that has no comparison among other pro sports franchises, made worse by the fact the franchise is worth over $2 billion, according to a recent Forbes magazine study.

There’s something bigger going on there, a deeper rot, having more to do with an organization being a country club more than a hockey club, compounded by decades of losing and the mental impediments it brings. 

And don’t give me the latest spin that this is a winning organization when you look at regular-season accomplishments of late. They haven’t won a Stanley Cup in 56 years. They just won their first playoff series in 19 years, beating Tampa Bay in the first round of the 2022-23 playoffs, before falling feebly in five games against Florida. For a team loaded up on offence-first skill players, they didn’t score more than two goals in seven straight playoff games.

So here we are, once again, at a crossroads. As they figure out which path they're going to take under new general manager Brad Treliving, here are our Top 5 Maple Leafs teams from yesteryear, going back to that Stanley Cup win in 1967, that could have done something but broke our achy-breaky hearts.

The 1992-93 Team That Was This Close

This version was probably the biggest heartbreak of these 56 years because it was a team that was so close to actually making the Stanley Cup final. But you can’t blame this one on management, coaching, dressing room culture or the decaying impact of having too much money.

The Leafs were led by Doug Gilmour, Dave Andreychuk, Wendel Clark, Dave Ellett, had Felix Potvin in goal, and were coached by the legendary Pat Burns. That team took out the favoured Detroit Red Wings in Round 1, off a Nikolai Borschevsky OT goal in Detroit in Game 7, then took out the St. Blues before facing the L.A. Kings in the Conference final. A win over the Kings meant they’d face the Habs for the Cup.

People have to understand that for Leafs fans of that generation, this was the first bit of positive news in decades after the incompetence during the Ballard years. So it really meant something. 

But a high stick by Kings captain Wayne Gretzky on Gilmour in Game 6 in L.A. – which drew blood, and was not called by referee Kerry Fraser for God knows what reason – then a Gretzky OT goal to drive a stake through their hearts, then back to Toronto for Game 7 where Gretzky scored three goals to twist the stake a little more, was an injustice fans in the Toronto market still talk and write about.

The 2022-23 Team Everyone Thought Would Break the Curse

This year’s version was right up there with 1993.

The Core 4, trade deadline acquisitions Ryan O’Reilly and Noel Acciari, players with legitimate playoff pedigree, a roster of skilled players seemingly callused and learned enough from years of playoff collapses, bottomless organizational resources tossed at coaching, technology, facilities, amenities, health and wellness support, then the first-round collapses of the heavily favoured Bruins and Colorado Avalanche, all suggested a path had been paved to a Cup.

After they took out Tampa, BetMGM had the Leafs as the most favoured among the remaining teams to win the Cup – 4.75, ahead of Dallas, Edmonton, Vegas, Carolina, Seattle, New York Rangers, New Jersey, and Florida. That moment, which lasted just a few days, was a shining beacon on a distant hill.

And then, after five games in the second round, it was gone. The next day, people were gassing up the golf carts, checking out how the Blue Jays were doing and heading to the cottage. The annual rite of spring in these parts.

After that loss, GM Kyle Dubas was fired over what appears to be an over-step in his contract negotiation with the club, according to what team president Brendan Shanahan said in his news conference and Brad Treliving was hired as the GM.

The 2001-02 Team, Mats Sundin's Best

This was probably the best of the Mats Sundin-led Leafs teams, and there were a bunch of good ones in there – when life was good before the salary cap came in, and if your franchise was flawed, you could spend your way out of any mistakes.

The Leafs finished with 100 points that year, were led by Sundin up front (80 points), had a roster that included Darcy Tucker, Alex Mogilny, Gary Roberts, Tie Domi, had Curtis Joseph in goal, and were coached by Pat Quinn.

That year they took out the Islanders in the quarter-finals, the Ottawa Senators in the semi-finals before losing to the Carolina Hurricanes in the Conference finals – going down four games to two.

A win would have meant a series against the Steve Yzerman-led Detroit Red Wings – who would take out the Hurricanes 4-1 and win the Cup that year.

The Promise of 1977-78 team

For those of a certain vintage, this was the heart of the Harold Ballard ownership years, when the penny-pinching curmudgeon sitting in his viewing perch at the old Maple Leaf Gardens (also called the “Carlton Street Cashbox”) somehow stumbled across a lineup of studs led by Darryl Sittler, Lanny McDonald, Tiger Williams, Borje Salming, Ian Turnbull, goalie Mike Palmateer as well as a solid core of character players, coached by the great Roger Neilson.

That year they beat the heavily favoured New York Islanders in the quarter-final – a team that the following season would launch into their dynasty period of four straight Cups. The Leafs would then fall to the Montreal Canadiens in the semi-final. The Habs were the greatest team in the galaxy in the late 1970s, so there was no shame in falling to them.

The belief was the Leafs had a core to build around and challenge the Habs and Islanders in the future, but Ballard would then fluff it all up.

The 1998-99 Team That Took Out the Flyers and Penguins

I have to apologize. My editor asked me to come up with five heartbreakers, five could-have-been-great contenders, and I struggled.

This was another version of the Sundin-led teams - 97 points, second in the Northeast Division, to the Senators, with Bryan Bedard, Sylvain Cote, Steve Thomas (with 28 goals), Alexander Karpovtsev (who led the NHL that year with +39), Joseph in goal.

That was the year they moved from the Gardens to the Air Canada Centre (now Scotiabank Arena). They would take out the Philadelphia Flyers and the Pittsburgh Penguins before falling to the Dominik Hasek-led Buffalo Sabres in the Conference Finals.

In the end, none of this matters. All this exercise does is likely trigger depression, so I apologize.

The Toronto Maple Leafs are a country club, not a hockey club. The people who have lived this in these parts understand it. And too much losing over too many decades places too much pressure on the shoulders of those young men who sign to play in Toronto. Each season of collapse and disappointment has a compounding effect. The Boston Bruins, on the other hand – now that’s a hockey club.

Summer will go by, and we’ll play some golf, we’ll start to forget about the playoffs, they’ll make some roster moves. We’ll all waddle back down to the Scotiabank Arena cashbox when the new season starts, with our Leaf flags and Carlton the Bear dolls, like lemmings, deluding ourselves that things will be different this time. Maybe that’s just the way it is, the way it will always be.