When did the Maple Leafs last win the Stanley Cup? Making a case for Toronto's chances in 2023/24 NHL season

The Toronto Maple Leafs have the longest Stanley Cup drought in the NHL but is the 2023-24 NHL season when it ends?

It's been well-documented that the Maple Leafs haven't won a Stanley Cup since 1967 when there were only six teams in the NHL.

Not winning a Cup since 1967 puts Toronto's Stanley Cup drought out to 55 seasons and the last time they made it to the Cup Final was also the same year. Since then, the Maple Leafs have lost five times in the Eastern Conference Finals which is a series away from the Stanley Cup Finals.

However, the Maple Leafs appear to be as closer as ever as Toronto has a solid team that finally got out of the first round this past year. With that, the 2023-24 Maple Leafs roster is likely the best chance for them to hoist the Cup.

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Why is this season the Toronto Maple Leafs' best chance?

The Toronto Maple Leafs have had this current core for a few seasons now but this opening night roster is likely the best it has been.

General Manager Brad Treliving knew the Maple Leafs weren't built to win in the playoffs as they were too small and not physical enough. With that, in the off-season, Treliving signed Tyler Bertuzzi, Max Domi, and Ryan Reaves who all play a physical role.

"There's a DNA in them that we need, a little more snot to our game," Treliving said in a press conference. "I feel better about our team (than after July 1). We were cognizant about trying to replace some offense, but there are also specific skill sets we're looking for."

Along with adding size, Toronto already has a skilled group of forwards, and it could be the final year for them.

The Maple Leafs have the core four of Auston Matthews, Mitch Marner, William Nylander, and John Tavares. All four could be perennial All-Stars but this is the last season Matthews and Nylander are under contract which makes it a must-win for the Leafs.

Finally, Toronto appears to finally have a goaltender as Ilya Samsonov impressed with his performance last season. He led Toronto to second place in their division and was doing well in the playoffs before he got hurt. But Joseph Woll proved he belongs as an NHL goaltender.

If Samsonov and Woll can stay healthy, it appears to be a good enough tandem to help Toronto end their Cup drought and win it all.