State of the Stanley Cup drought: How close are the Maple Leafs to winning?

Playoff success has been hard to come by in Toronto and the Maple Leafs have an uncertain future ahead of them.

This is Part 10 of a 10-part series examining the longest Stanley Cup droughts in the NHL, and how close teams are to breaking through for their first championship in decades — or ever.

Previous articles: Senators, Sharks, Oilers, Flames, Islanders, Coyotes, Flyers, Canucks, Sabres

The Toronto Maple Leafs' Stanley Cup drought is extraordinarily well known around the league and completely synonymous with the franchise. There are plenty of NHL teams that don't get nearly as much attention as the Maple Leafs' inability to win a championship.

When Toronto drafted Auston Matthews first overall in 2016 and he almost instantly fulfilled his promise as a franchise player, it appeared the team had a foundation to become a contender for years to come. But while the Maple Leafs have put together some strong teams during the Matthews era, those squads have consistently failed to make a mark in the playoffs.

Following another disappointing postseason in 2022-23 — albeit one that included a series win for the first time since 2003-04 — the Maple Leafs appeared likely to shake things up.

That happened in the front office, as Kyle Dubas was replaced by Brad Treliving, but surprisingly head coach Sheldon Keefe was retained. The team's high-profile quartet of top forwards — Matthews, Mitch Marner, John Tavares and William Nylander — also remained together.

Toronto did a little bit of tweaking in the offseason, as the team added Tyler Bertuzzi, Max Domi, John Klingberg and Ryan Reaves. Meanwhile the Maple Leafs lost Ryan O'Reilly, Michael Bunting, Luke Schenn Justin Holl, and Noel Acciari to free agency.

It'd be hard to call that a clear net win, but the new additions could help the team's depth scoring, and the intangible element of nastiness Treliving has brought in may pay dividends. Overall, the Maple Leafs look to be approximately what they've been for most of the last few years. They have the talent to win it all, but there are still a few teams that look better on paper.

Breaking the team's epic Stanley Cup drought would require a magical playoff run where things break right for the team.

That's not the kind of outcome Toronto's fanbase has come to expect.

The Auston Matthews era has resulted in one playoff series win for the Maple Leafs. (Fred Vuich/AP)
The Auston Matthews era has resulted in one playoff series win for the Maple Leafs. (Fred Vuich/AP)

Here's a look at the state of the Maple Leafs' Stanley Cup drought:

How long has it been?

The Maple Leafs have not won a title in 55 seasons.

How close have the Maple Leafs come?

Not particularly close, compared to some of the other teams with lengthy droughts.

The Maple Leafs have not made the Stanley Cup Final since 1966-67, and they haven't won the Presidents' Trophy since 1962-63 — meaning they haven't put together any regular-season juggernauts that fizzled out.

In 55 seasons, Toronto has reached the NHL's final four just five times (1978, 1993, 1994, 1999, and 2002).

Not all of those playoff runs meet the criteria of a close call. In 1978, the Maple Leafs were swept by a Montreal Canadiens team that went 59-10-11 during the regular season on the way to a title. In 1994, they only won one game against the Vancouver Canucks — scoring just nine goals in the series.

In 1998, Toronto fell in five games again, this time to a Buffalo Sabres team that got Dominik Hašek back from injury in Game 3 and earned multi-goal wins in each of the last three games of the series.

The Maple Leafs got closer in 2002, taking the Carolina Hurricanes to six games, in a series that included four overtime matchups and just one multi-goal win. The shots were almost dead even (159-158 Carolina), but Artus Irbe shut the door on the Maple Leafs, conceding just six goals and posting a .962 save percentage.

That was a bit of bad luck for a Toronto team that ranked third in goal scoring during the regular season — especially considering Irbe's save percentage was just .902 during 2001-02. Even so, the Maple Leafs would've been heavy underdogs if they'd made the Stanley Cup Final facing a Detroit Red Wings squad that won the Presidents' Trophy with 116 points.

Detroit handled the Carolina team that Toronto couldn't beat in five games — outscoring them 14-7.

When Maple Leafs fans want to get into what-if mode, the season they tend to fixate on is 1992-93. That's because of the team led by Doug Gilmour — who came second in Hart Trophy voting with a 127-point season — and a young Félix Potvin got within a goal of the Stanley Cup Final.

Toronto earned a 3-2 lead in the Campbell Conference finals against Wayne Gretzky's Los Angeles Kings, but lost Game 6 in infamous fashion. Gretzky clearly got Gilmour in the face with his stick in overtime, and after that play went uncalled, he was able to score the winner.

Los Angeles then won Game 7 by a score of 5-4 and went to the Stanley Cup Final.

It's understandable that Maple Leafs feel aggrieved by that series of events, but the 1992-93 team still had plenty of hurdles ahead of it, even if Gretzky hadn't scored in the immediate aftermath of an officiating mistake. Los Angeles may have won Game 6 anyway on a later goal — and if the Maple Leafs found their way to the 1993 Stanley Cup Final, the Canadiens team they would have found there was no joke.

Montreal had a better record than Toronto during the regular season, and Patrick Roy was on a tear in those playoffs. The Canadiens dispatched the Kings in five games, and the Maple Leafs easily could have suffered a similar fate.

How does Toronto's championship prognosis look now?

OK, but cloudy.

The Maple Leafs have their sights set on Stanley Cup contention in 2023-24, but this is a tough franchise to project too far into the future.

Matthews is expected to sign a contract extension at some point, but as it stands, he's only under contract for one more season. Nylander is in the same boat, and his negotiations with the team appear to be more contentious. The Swede has a 10-team no-trade list, but it's possible he gets dealt if talks break down completely.

Even Marner and Taveras are only on the books for two more seasons, making it tough to predict what this team looks like a few years out.

Toronto's best option might be to retain its top guys, as few players of their calibre reach free agency and they would be difficult to replace. At the same time, the Maple Leafs are likely wary of obliterating their cap sheet to preserve the Core Four at all costs. It's a delicate situation.

If the team's top-end forward group is not retained, the Maple Leafs will be relying on abundant cap space to replace them as their prospect pool isn't low on blue-chip types outside of Matthew Knies, who debuted last season.

The version of the Maple Leafs we've seen in recent years hasn't been able to break through, and its tough to envision what the next era could look like in Toronto until we see how things shake up with the big guns.

Outside of the forward group, the defence core has little long-term stability as only Morgan Rielly is signed beyond 2024-25 and Ilya Samsonov may or may not be a goaltender the team can count on. The Russian is coming off a stellar 2022-23, but he's never started more than 40 games in a season. Even if he proves his mettle as a full-time starter next season, he'll become an unrestricted free agent at its conclusion.

As a result, it's tough to say the Maple Leafs are in great shape over the long haul.

Their 2023-24 team still projects to be a strong group, though. As long as they can keep Matthews in town they'll have a foundation to build around, but we've already seen that his presence alone is no guarantee of playoff success.