Reliving the biggest “what ifs” from the Toronto Maple Leafs core four era

Over the years, the Toronto Maple Leafs have made numerous bad moves that have left the fans wondering “what if?” There are so many moves that look terrible in hindsight, such as leaving Jared McCann unprotected in the expansion draft, trading away Nazem Kadri, letting Zach Hyman walk in free agency, and much more.

However, some of the biggest “what ifs” in this era did not happen in the front office. Instead, they happened during the heartbreaking playoff losses over the years. On numerous occasions, the Leafs have been mere inches away from completely changing the narrative, but instead have found themselves on the wrong side of history. In nine years with the best team in Leafs history, the deepest playoff run they ever made was 7/16 wins, not even half of what they needed to win it all.

With just a little more puck luck, the Leafs could have done far more than simply win more than seven games in a single playoff run; they easily could have won it all.

2021 loss vs Montreal

The Leafs should have swept the Habs this year, and it is an absolute miracle that the Habs managed not only to win the series but to come back from down 3–1. This article would be thousands of words long if I were to go over every missed chance in this series, but the worst of them all occurred in Game 6 overtime.

The Leafs played one of the most dominant periods of hockey I have ever seen them play and still managed to lose on Montreal’s third shot of OT. Out of all the chances the Leafs had to end it, the worst came eight minutes into the extra frame, where Carey Price robbed Auston Matthews on the backhand after a flurry of chances. All he had to do was shoot it a bit further left or simply raise the puck, but instead Matthews and the Leafs ended up with one of the worst blown series in recent history.

2022 loss vs Tampa Bay

The 2022 Leafs team was truly the one that got away, in my opinion. Sixty goals from Auston Matthews and a final record of 54–21–7, good for 115 points (the most in franchise history).

When looking back at this series, two moments come to mind instantly (Cal Foote phantom high stick and Holl interference), but there are another few plays that could have changed the course of the series. First off, the Leafs got absolutely jobbed by the refs in Games 6 and 7. In Game 6, David Kampf got a high-sticking penalty on Cal Foote even though his stick didn’t touch his face, eventually leading to the game-tying third-period goal. In Game 7, John Tavares scored a huge game-tying goal that was immediately called off for interference by Justin Holl, a play that is called a penalty maybe 1/100 times.

Despite this, the two biggest what-ifs occurred during the Game 6 overtime. Once again, the Leafs absolutely dominated this overtime from start to finish and had many chances to end this one, including all three of Nylander, Matthews, and Marner getting point-blank chances before the halfway point of the extra frame. The biggest chance of them all came just over a minute in, where John Tavares sprung Alex Kerfoot on a clear-cut breakaway with a chance to end the series, but he was unable to finish. If that wasn’t bad enough, Tampa’s game-winning goal was actually an own goal. As the puck slowly trickled in, Justin Holl and Michael Bunting both tried to clear it at the same time and pinched the puck into the net, ending the game. If the Leafs got just a little bit of luck on any of these plays, who knows how deep of a run they could have gone on.

2023 loss vs Florida

Although this series was over quickly, it was way closer than it seemed. After Bobrovsky stood on his head in the first three games, stealing three wins from Toronto, the Leafs found themselves on the verge of being swept. They forced a Game 5 at home and went into the third down one, but fans believe it should have been tied because Morgan Rielly’s goal should have counted.

Although this is debatable, this isn’t really the biggest what-if from this game. After forcing overtime, the Leafs had not one but two clear-cut breakaways. Unfortunately, the players who got these chances were Alex Kerfoot and Calle Jarnkrok, and both of them made feeble attempts. Although the Leafs would still have had to win two more to advance, who knows what could have happened if they finished on either of these chances, as they had dominated the series in chances up until the final whistle.

2024 loss vs Boston

This series ended in the worst possible heartbreak in sports, a Game 7 overtime loss. After forcing a Game 7 down 3–1, the Leafs scored the first goal of the game and took the lead nine minutes into the third period. Everyone remembers what happened not even two minutes later, with Hampus Lindholm tying the game at one, leading to the eventual overtime loss, but not many people remember what happened a mere 30 seconds after the goal.

Mitch Marner made a beautiful breakaway pass to Joel Edmundson, of all people, who is probably the last player you would want in that situation. Swayman made an easy pad save, keeping Boston alive and leading to Lindholm’s goal one minute later. This team likely wouldn’t have stood a chance against Florida, but it would have been pretty nice to finally beat the Bruins.

2025 Loss vs Florida

The deepest playoff run of the Core 4 era left fans wondering “what if?” more than ever before. First off, in Game 4 of the Ottawa Senators series, Matthews dinged the puck off the post point-blank in overtime, an overtime in which they eventually lost. The Leafs would go on to luckily win the series by the skin of their teeth, but an overtime series winner definitely would have changed the narrative around Matthews.

The worst what-if of this playoff run came in Game 3 against Florida, a game in which the Leafs led by two goals at one point. Although they blew the lead, they still had a chance to go up 3–0 in the series. The score was 4–4 late in the third, almost certainly a next-goal-wins situation. With just three minutes left in the period, Morgan Rielly carried the puck into the zone and took a shot. Although it was a bad angle, the puck dinged off the crossbar and out. The Leafs were quite literally one inch away from taking a 3–0 series lead and almost definitely making the conference final. Although we can’t be sure, it really did seem like the Leafs would have beaten the Hurricanes and Oilers en route to their first Stanley Cup in 58 years.

So many missed opportunities

Reflecting on these painful moments is excruciating, but it is also very telling. On several occasions, they were only a bounce, a save, or a few inches away from changing the course of franchise history. Had just a handful of moments gone differently, the perception of this team would be entirely different. As we Leafs fans watch Mitch Marner likely win a Stanley Cup and Conn Smythe in his first year with Vegas, all we can do is wonder what could have been.

If only a few of those moments had gone Toronto’s way, perhaps the Core Four era would be remembered not for its utter failure, but for a Stanley Cup.