The Top 10 "Leafiest" Things to Ever Happen in Toronto Maple Leafs History

The Toronto Maple Leafs have not won a Stanley Cup since 1967, when the NHL had just six teams, and not only that, but a team that didn't exist when the Leafs started building their current roster has already won one.

When something is self-evidently bad, and then made somehow worse by circumstances that are not only ridiculous and stupid, but also extremely unlikely and improbable, and which could only reasonably happen to the Toronto Maple Leafs, then that is when something is "Leafy."

The Golden Knights winning the Stanley Cup was already one of the Leafiest things to ever happen, but being as we are talking about the hockey team from Toronto, I can use it as an example and not even include it in my top-ten list!

That's Leafy in itself. You could even dig down deeper and suggest that the Leafs could have had Alex Pietrangelo as a UFA instead of John Tavares, and had they chosen differently, perhaps they would have won that Stanley Cup instead. It's Leafs-ception!

Other examples of Leafy things that won't even make this list: Not appearing in the Stanley Cup Final since there were six teams; not winning a scoring title, Norris Trophy or Vezina Trophy in the same period; having more players from Ontario play in the NHL than any other place in the world, but still failing to ever win, etc. Then there is Harold Ballard - there's probably another ten or twenty Leafy things that guy alone caused, but most of them were before I was watching hockey.

By now you get the point, so here are the top 10 Leafiest Things to Ever happen.

The Top 10 "Leafiest" Things to Ever Happen in Toronto Maple Leafs History

10. Joe Sakic vs Luke Richardson

The Toronto Maple Leafs are notorious for making terrible decisions at the NHL Entry Draft, but this infamous error will haunt the franchise eternally.

As detailed here by Gord Stellick, at the 1987 NHL Entry Draft, the Leafs head scout, Floyd Smith, tried unsuccessfully to convince GM Gerry McNamara to use the 7th overall pick on Joe Sakic.

Apparently, a huge argument ensued on the draft floor, but no one's mind was changed and the Leafs went with their original pick - defensive defenseman Luke Richardson.

Richardson would play just four seasons for the Leafs, and although he would go on to play nearly 1500 NHL games, he was never a star, and picking Joe Sakic would have, you know, drastically altered NHL history as we know it.

Joe Sakic, one of the best players to ever live, is the 9th highest scoring player in NHL history and won two Stanley Cups.

It is one thing for the Leafs to draft Travis Dermott one spot ahead of Sebastian Aho, but that's a total fluke and every team has that happen to them. This is different because the team's head scout argued passionately for the Leafs to take Sakic and they ignored him.

Had they taken Sakic, they likely never trade for Gilmour, maybe not even Sundin - who knows? All we know is that if the Leafs made the correct choice that day in 1987 Auston Matthews would still be the second-best player in Franchise History at this exact moment.

And that is what makes this one of the Leafiest Things to Ever Happen - they didn't just pick the wrong player; the player they passed on would have been the best player in Franchise History.

9. Wayne Gretzky

Before he disgraced himself by selling gambling ads and making people uncomfortable with his political views, Wayne Gretzky was the greatest hockey player to ever live.

He owns virtually every scoring record known to man, and is the all-time highest scorer with 894 career goals. In a world where even the most basic fact is contested, not a single hockey fan thinks anyone but Wayne Gretzky is the best of all-time - there just isn't even a close option to argue about.

As everyone knows, he started his career with the Oilers and then went to the Kings before finishing up with the Blues and Rangers.

It was in the latter part of his career where he almost joined the Toronto Maple Leafs. According to Sportsnet's Scott Morrison, Gretzky almost joined the Leafs in 1996.

With GM Cliff Fletcher at the helm, Gretzky was a UFA and the Leafs were intent on bringing him home. Had he joined the Leafs, things could be incredibly different today - who knows?

Gretzky had declined by this point, but he still had multiple 90 point seasons left in him. An old Gretzky would have been significantly better than just about any other player in team history, and its just a shame that this didn't happen.

Insanely, both the Leafs and Gretzky wanted this to happen and a deal was in the works before the Leafs owners nixed the deal. If this had happened ten years earlier, it would be number-one on this list, but regardless, the fact that the Leafs could have had the best player to ever live on their team, even at the end of his career, and didn't, is a complete joke.

8. McDavid Lottery

In 2015, the Edmonton Oilers won the lottery that allowed them to select Connor McDavid first overall. This was, and is, a complete joke because the Oilers ended up having the first overall pick in four out of six years.

Somehow they were rewarded for being one of the worst franchises ever with the second-best player to ever live, but complaining about that isn't why we are here.

The Leafs, as you most likely are aware, drafted fourth that season and came away with Mitch Marner, who may yet go down as the second-best player to ever wear the blue and white. So this was already a good draft, but it could have been so much better.

The Leafs entered the lottery with the fourth-best odds to land McDavid. That in itself was pretty fun, but the odds were very weighted in Edmonton's favor so there wasn't really too much of a reason to get excited.

Being a Leafs fan, I didn't get my hopes up or even consider that McDavid would land in Toronto. However, as the lottery was happening, one of the Leafiest things to ever happen went down.

Connor McDavid, who is from Newmarket (a suburb of Toronto) grew up a huge Toronto Maple Leafs fan, and him and everyone he knows, plus everyone in the GTA, were cheering for the Leafs to win the lottery.

And it almost happened. The NHL draws four numbers, and after they drew the first three, the Leafs had the best odds of winning. Of course they did.

But is Connor McDavid on the Leafs? No he is not, but he is the 8th most Leafy thing to ever happen.

7. Covid Hurts the Leafs More Than Any Team

The Covid Pandemic led to a flat salary cap that didn't go up for four years, and while each and every NHL team was affected, there was one team that was affected the most.

Do I even need to say which team?

The Toronto Maple Leafs were a very exciting team in 2019 but things got off to a rough start and Mike Babcock was fired in one of the most surprising turn of events in team history.

Sheldon Keefe came in and things were quickly back on track.....until the season was abruptly put on hold and the world was thrust into chaos. Obviously there were a lot worse things going on back then than what happened to a hockey team, but given we're talking about the Leafs, it should not come as any surprise that they were the NHL team hurt the most by the pandemic.

The reason is the timing of the Leafs star players needing new contracts.

A year before, the Leafs gave out the biggest UFA contract in history to John Tavares. The reason they felt comfortable doing this with new contracts coming up for Matthews, Marner and Nylander was because the NHL salary cap was expected to sky-rocket after the 19-20 season, due to the convergence of three separate money makers for the NHL.

The NHL was expanding, gambling was now legal and a new TV deal was on the horizon. These three things were each supposed to send the salary cap straight up. Unfortunately, those three things just ended up helping the league stay in business rather than making it extremely rich.

The pandemic froze the cap at the worst possible time for the Toronto Maple Leafs. "We can, and we will" turned into "we can't afford a better defenseman or goalie."

The fact that the Leafs were a competitive team the entire time the cap was flat, even once having the NHL's best roster in 2023, shows that GM Kyle Dubas was right to employ the Studs and Duds Salary Cap Strategy. The fact that the Leafs almost won regardless is impressive, but it only leads to further cries of "What If?"

6. Eric Lindros and Scott Niedermeyer

The funniest thing about the Toronto Maple Leafs might just be that this isn't number-one on the list, but just the half-way point.

Once upon a time, the Leafs were a brutally bad team set to draft first overall and select the best player to enter the NHL in a decade.

The reward for being the worst team of the 80s was going to be the glory of building a team around the most exciting player to enter the NHL since Wayne Gretzky. Eric Lindros was not only a new kind of NHL player - a huge monster who could also skate and score - but he actually ended up living up to the enormous hype.

And only because of the worst management in the history of pro sports did he fail to do so with the Toronto Maple Leafs.

Had the 1990-91 NHL season taken it's natural course, the Leafs very well could have finished in last place and selected Eric Lindros. It is a near certainty that they would have. The Leafs, however, had previously traded their 1991 draft pick, back in 1989, to the New Jersey Devils in exchange for Tom Kurvers.

The Leafs, as mentioned here by Steve Dangle, then went on to start the 1990-91 season 1-9-1, which should have been the best thing to ever happen. All that was left was to sell of parts and then draft Eric Lindros.

But since they didn't have their draft pick, they actually made moves to avoid finishing last. They traded prospects to the Nordiques in exchange for their best players to ensure it would happen.

The end result was that they "only" ended up giving away Scott Niedermayer instead of Eric Lindros. The only problem? Niedermayer was second only to Nik Lidstrom as the best defenseman of his generation and is now a hall of famer who arguably ended up having a better career than Lindros himself.

The fact that this isn't number-one on this list could in itself be an entry on the list.

5. Kerry Fraser

The words "Kerry Fraser" send chills down the spine of Leafs fans as if someone was saying "Freddie Krueger" and it was a known fact that he was a real guy who could actually haunt your dreams.

While it has never been substantiated that Kerry Fraser actually does have the power to enter your dreams and ruin your favorite team's hockey season, it is almost believable that he can.

Back in 1993, I was just 11 years old. The Toronto Maple Leafs were not so much a passion at that time as a full time obsession. I played goalie on my Atom team. I considered Felix Potvin to be my best friend. We played road hockey seven days a week. We rode our bikes two concessions over to visit the card shop conveniently located in the back of the country store our parents would send us with notes to buy cigarettes for them at.

I had Score, Fleer Ultra, Upper Deck, O-Pee-Chee and Leaf. But most of all, I had Wendel Clark and Doug Gilmour. I can still remember where I was when Nikolai Borschevsky became famous.

I was convinced the Leafs were a team of destiny who would win the Stanley Cup, and I would have been right, if not for that monster, Kerry Fraser.

As you most likely already know, the Leafs were winning heading into Game Six 3 games to 2, and the game went to overtime. Tied at four and with the Leafs on the PK, Wayne Gretzky high-sticked Doug Gilmour in the face, drawing blood.

This should have been an automatic five-minute major penalty and game misconduct. With the Leafs on a 5 minute power-play with Gretzky ejected, they most likely would have won the game and went on to play the Montreal Canadiens in the Stanley Cup Final.

Instead, Kerry Fraser, who claims to have not seen the play, even though it was a power-play and involved the two best players and the puck in the offense zone, ignored the play and Gretzky (who else?) scored the winning goal seconds later.

Fraser can claim he missed the call all he wants, I will always believe that he just didn't have the guts to call a major penalty on Wayne Gretzky in OT in the Playoffs. At least Freddy Krueger dispatches his victims with honour!

3. Zach Hyman

If you had a player up for a new contract and he wanted to more than double his money, at the age of 30, and he wanted to sign for the maximum length, which would have run the contract into his late thirties, and if he had a history of playing poorly in the playoffs, two bad knees, a lengthy injury history and a play style that made it seem like he'd be injured more often than he'd play, and if that player had a career high of only 41 points, it would be a no-brainer to let him walk in free-agency.

Unless you are the Leafs, then that no-brainer would turn out to be the worst decision you ever made.

When the Oilers showed up to give Hyman more money and term than any reasonable person would think was smart, the Leafs were only too happy to drive him to the airport.

But like Nazem Kadri before him, Zach Hyman's departure would haunt the Leafs in almost unimaginable ways.

Hyman (who would have been happy to be a career fourth liner based on long odds of him even making the NHL when Kyle Dubas first acquired him) ascending to become a franchise player and one of the best players in the NHL wasn't even something considered to be in the realm of possibility.

But then again, this is the Leafs we are talking about, so maybe we should have known better. After Hyman left Toronto, he scored 27 goals and made the Leafs look pretty dumb.

The next year he scored 36 times and scored 83 points, which made them look even dumber. But last year was something no one could have imagined. Hyman scored 54 goals and another 16 in the playoffs for a total of 70 on the season, while his team came within one game of winning the Stanley Cup.

This doesn't happen. In the NHL, players just do not improve and have their best seasons at age 32. Unless, of course, they are smarting from rejection from the Toronto Maple Leafs, in which case it becomes almost routine.

2. 0-11 in Elimination Games

If you read this far, you must be thinking "there is no way all this stuff happened to one team - they are like a reverse Forrest Gump in hockey team form."

And you'd be right, but it's all real.

And I didn't even get to the two worst things yet, so prepare yourself.

in 2016, the Toronto Maple Leafs made a surprise appearance in the Stanley Cup Playoffs. It was Auston Matthews rookie season, and no one expected them to make it, but they did. They went down to the Capitals 4 games to 2. They were just happy to be there. They hadn't made the playoffs since 2013 when they lost in the worst possible fashion to, who else, the Boston Bruins.

But things started getting weird the very next year.

Down 3-1 to Boston, the Leafs climbed all the way back but lost Game 7.

The next year they played Boston again and were up 3-2 before losing both of the last two games. Significantly, they had now lost four games in a row where they could have eliminated their opponent (counting 2013).

in 2020 they lost the fifth and deciding game to the Columbus Blue Jackets. In 2021 they were up 3-1 on Montreal but lost three games in a row. They are now up to an almost incomprehensible eight game losing streak while having their opponents face elimination.

Unfortunately, the very next year they had to play the Lightning and lost another two games with their opponents on the ropes. Ten times in a row the Leafs had a chance to get to the second round and they lost all ten times.

The next year it was Tampa again, and once again with the chance to put their opponent away, the Leafs lost. That made it 11 in a row. That might seem pretty bad, but people started to do the math and it's so much worse than you thought.

The odds of this happening were 1 time in 10, 000. Put another way, according to the link above from Yahoo, if you found gambling odds that were +100,000, which you basically can't even do, they would have a 10x higher chance of happening than what happened to the Leafs.

So keep that in mind the next time you're ripping on Kyle Dubas - he quite literally has the unluckiest record of any GM in the history of the NHL.

1. Bryan Berard

Well, we have come to the end, and I have to admit, it's been sort of fun. Depressing, but still amusing....like listening to Disintegration by the Cure.

That said, I hate to end it on this one because it's more tragic than hilarious. The fact is, despite all the improbable things that have happened, this one is the worst and maybe even the most improbable.

In 1998 the Leafs made one of the only great trades they have ever made when they sent former top goalie Felix Potvin to the Islanders for Bryan Berard.

Berard had only recently been drafted first overall and was only 21 when the Leafs acquired him. He immiediately became the most exciting young player the Leafs had ever had, or would have until they drafted Auston Matthews.

Berard was just starting to live up to his potential - which was to become the best defenseman in franchise history - when he was struck in the eye by an errant stick from Ottawa Senators player Marrian Hossa.

This accident cost Berard his vision and pretty much his career. The Leafs were just starting to be a contender and with Berard winning a bunch of Norris Trophies may have won it all - who knows?

To get an idea of just how good Berard could have been, consider that after he came back to the NHL he had a season with the Blackhawks where he scored 47 points in 58 games. Adjusted for having just one working eye, that is one hell of a season.

Berard was retired by 30 and only ended up playing 619 NHL games. Despite how dangerous hockey seems, this is the only permanent career ending eye injury I am aware of.

There have been over 30, 000 NHL games since the year 2000 and so the odds of this happening seem to be even lower than the 11 games losing streak with a chance to move on.

This heartbreaking event is bad enough for anyone to go through, but the fact that it happened to the Leafs with arguably the best defenseman they have ever had, at a time when having him probably would have made them the best team in the league and helped them win a Championship, makes it the Leafiest thing to ever happen.