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“At the time I thought, we’ll get more Cups — lots of them, probably,” Powell said.

Fifty-seven years later and counting, Powell laughed.

“Well, that didn’t exactly pan out like I thought,” he said.

It’s hard to fathom that there was a time when the Leafs were the toast of hockey, and winners of four of the most recent six Cups, unless you’re of a certain age. As Dave Hodge, the legendary broadcaster who attended the 1967 Stanley Cup parade, said recently: “It didn’t seem then like (that parade) would matter like it has … If you knew it wasn’t going to happen again, maybe in your lifetime, you’d view it differently.”

Can you imagine another parade, with this group? If the past eight post-season runs have confirmed anything, it’s that the Shanaplan Leafs are uniquely inept in navigating the specific rigours of playoff hockey, and in some ways it’s taken a decade to come full circle. When MLSE CEO Tim Leiweke introduced Shanahan as the Leafs’ new president in 2014, Leiweke painted a bleak picture of Leafland, where the team had missed the playoffs in eight of the previous nine seasons.

“I spend a lot of time talking about culture and character … I’m not sure the Leafs have it,” Leiweke said. “I definitely sense we lack an identity, and right now we’re a team that lacks direction.”

In the next breath Leiweke feted Shanahan as a deft “architect” who’d been brought aboard “to get this right, to make sure we don’t have further conversations about culture, accountability or discipline.”

A little more than 10 years later, head coach Craig Berube was hired last month as the franchise’s new keeper of “accountability.” Exactly who is now in charge of “culture” and “discipline” is anyone’s guess.

We know one thing: there’s never been a team quite like the Shanaplan Maple Leafs. They boast a .636 regular-season points percentage since 2016-17; only Boston and Tampa have been better. Their playoff win percentage over that span, however, is a dismal .421, worst among the 16 teams that have played at least 50 playoff games. According to Randy Robles of the Elias Sports Bureau, there’s never been a team that’s been as good as the Leafs in the regular season and as bad as the Leafs in the playoffs over any eight-year span.

The playoffs are a different animal. And the Leafs have yet to figure out how to handle the beast.

The easiest explanation is roster construction. Toronto’s choice to fork over about 50 per cent of the salary cap to Auston Matthews, Mitch Marner, William Nylander and John Tavares made it harder to acquire or retain adequate goaltending, defencemen and forward depth, especially once COVID slowed any growth in the league’s salary cap. Sure.

But more, the Core Four themselves didn’t live up to their importance when it mattered most. No one doubts the individual skill; it’s the combination that has been less than the sum of its parts. No team has scored more regular-season goals than the Leafs since Toronto’s return to the playoffs in 2017, but among teams that have played over 40 playoff games in that time, the Leafs rank 16th of 16. Only Edmonton and Tampa had a better regular-season power play in the past eight years, but 15 teams have had better playoff power plays since 2017. pc28����is a team built on an offence that repeatedly disappears when it matters.

It wasn’t supposed to be like this. After Shanahan engineered a deft tank job that saw the Leafs finish dead last and win the 2016 NHL draft lottery — and with it the right to draft Matthews, with Marner, Nylander and defenceman Morgan Rielly already in the organization — the future seemed limitless.

By 2017, then-Blackhawks coach Joel Quenneville was comparing Toronto’s young roster to the 2008-09 Chicago Blackhawks. Quenneville, of course, led Chicago to Stanley Cups in 2010, 2013 and 2015.

After the Leafs gave the Presidents’ Trophy-winning Washington Capitals a run in the 2017 playoffs — playing five overtime games in a six-game series defeat — there were some who considered the dream realistic.

“We all want the Stanley Cup in our hands,” Nazem Kadri, the veteran Leafs centre, said after that season-ending loss to the Capitals. “We realize we’ve still got some work to do, but I think that the process has sped up a little bit.”

Their Atlantic Division opponents had something to say about that. The following two seasons brought first-round Game 7 losses in Boston. The 2018 edition came with season-ending murmurs of a rift between head coach Mike Babcock and Matthews; the 2019 edition, which saw the Leafs blow a 3-2 series lead, came with obvious scapegoats. There was Kadri, suspended for a second time in two post-seasons. There was goaltender Frederik Andersen, a regular-season stalwart who wasn’t good enough in the clutch. There was Jake Gardiner.��

Then in 2019, the first real worry: the Leafs had a chance to close out the series in Game 6, only to freeze for extended stretches after giving up a 1-0 lead. A little adversity was enough to sink them.

Kadri was traded and Gardiner left, but the playoff losses kept coming. After Babcock’s firing that November, the 2020 and 2021 Leafs lost in the opening round to Columbus and Montreal, respectively — teams so flawed neither has been to the playoffs since. In 2020, before COVID and the eventual loss to the Blue Jackets, veteran defenceman Jake Muzzin — the rare Leafs veteran with Cup experience — had tried to raise an alarm. At one point he said: “We’ve got to find the urgency, the passion, the love of the game, the love to compete for each other. All of that needs to come. I don’t know why it’s not there. I think sometimes, like I’ve touched on earlier, when we struggle, we want the easy game.”

After the Columbus series, Shanahan spoke of the need for more “grit and work ethic” — an indictment of general manager Kyle Dubas’ insistence on stocking the lineup with one-dimensional skill. After the Montreal loss, Shanahan said the franchise was searching for “killer instinct”, which appeared to be an indictment of both Dubas and the core players. Oh, and after Andersen signed with Carolina as a 2021 free agent, pc28����continued that eternal search for dependable goaltending.

But it was the Montreal loss that was a blazing, scarlet red flag. It said something that the Leafs invited cameras in to record that defining failure for the Amazon documentary series “All or Nothing”. They must have thought that in a cakewalk all-Canada division, with a garden path laid out to the conference final, a documentary would come out well. That season was a chance at playoff redemption, all but wrapped in a bow.

It turned into a nightmare. The Leafs opened a 3-1 series lead and lost Game 5. Before overtime in Game 6, head coach Sheldon Keefe was filmed challenging his team to meet the moment. He told Matthews and Marner and Zach Hyman that their line was getting dominated. He told his team they were playing tight. He said: “This is it. This is the time. These are the f—-ing moments you’re remembered for. All the other s—t doesn’t f—-ing matter. This is it. You want to be a great team? You want to be great f—-ing players? You got to push through.”

The Leafs outshot Montreal 13-2 in OT before Travis Dermott lost a puck and pc28����lost Game 6. Before Game 7, assistant coach Paul MacLean was recorded in a coaches meeting saying the Leafs were — in their heads, in their car, under the bed. Said MacLean: “The biggest obstacle this team has now is themselves.”

A source close to the ice looked at the Leafs in Game 7 warmups and saw a tight team, and they played like it. “All Or Nothing” became all for nothing.

That was the moment the Leafs’ core could have been broken apart and reassembled. Shanahan won Stanley Cups and gold medals as a player; he values how athletes perform in the biggest games. But Shanahan also preached patience, which made sense in isolation. Shanahan’s predecessor, Brian Burke, tried to go faster and faceplanted.

“We are going to do this in pc28����with this group. We are going to get this done,” Shanahan said in 2021.

Was it faith? Ego? An all-in insistence that this core could work, despite the evidence? Whatever it was, it was a mistake in judgment. The loss to Tampa in seven in 2022 was a close series, at least. Beating Tampa in 2023 ended the longest playoff series drought in the NHL at 19 years, and there was a hope that would dispel the weight of the past. As Matthews said at the time: “It’s huge mentally for us, just to get that monkey off the back.”

But in the front office, some naturally worried a letdown would follow. pc28����dropped the first two games of the second round at home to the Florida Panthers. Then came a defining Game 3. It was the Leafs’ first no-doubt must-win of the season —��the kind of game where big players come up big, the kind Shanahan valued.

Matthews and Marner were buried by the��Aleksander Barkov line. Tavares, too, by lesser players. Nylander was effective, but it wasn’t enough.

Game 3 was where the faith in this core finally fractured for some members of the organization and, according to sources, Dubas was among them. That faith had already wobbled late in the season; some in the front office decided the core players simply didn’t hate losing enough. When they didn’t show up in the biggest moments, when they failed to create the right habits, it was seen as a measure of that essential thing.

That wasn’t the whole picture, of course. The counterargument, circulated by various allies of the Core Four, was that the Leafs never had an elite goaltender, or a traditional No. 1 defenceman, or enough depth scoring. The counterpoint to that, of course, was that had the Core Four taken a little less money, there would have been more money for extras. Round and round it went. Round and round it goes.

Every year, the team has tacked on depth players to provide what the core lacks; in 2023, they did their best job yet with Ryan O’Reilly and Luke Schenn — two players with Cups��— as well as Jake McCabe, Noel Acciari and Sam Lafferty. At one point Dubas stood on the catwalk in Seattle and said, right before making the McCabe trade, “If I’m going down, I’m going down my way.”

But even then, McCabe joined a list of the veteran additions who came without championship experience, and in some cases whose teams were notorious for falling short of title expectations: Patrick Marleau, Jason Spezza, Joe Thornton, Nick Foligno, Mark Giordano. Keefe was a rookie NHL coach, just like Dubas was a first-time GM, and Shanahan was a first-time president.

All those became problems. But the big four contracts were based on a belief that the Core Four were worth it. And if they simply delivered, this could have worked. Remember, the Leafs were one ping-pong ball away from Connor McDavid, a year before Matthews. They took Marner six spots before Colorado took Mikko Rantanen. They took Nylander four spots after Edmonton grabbed Leon Draisaitl, after a year in which the Burke regime signed David Clarkson as a free agent to bolster a doomed team. And that 2013 playoff appearance — an aberration in a dark time — came the year Nathan MacKinnon went No. 1.

Among those with at least 50 appearances, McDavid is third in playoff points per game, after Wayne Gretzky and Mario Lemieux, and dragged the Oilers to Game 7 of this past Cup final. Draisaitl ranks fourth on that list, MacKinnon fifth, Rantanen seventh, behind Mark Messier. And Steven Stamkos, who passed on pc28����a year before Tavares said yes, has 61 points in 78 playoff games since, to Tavares’s 24 in 38.��

The Leafs just missed. It’s one thing to avoid elimination, but the hardest games are the ones where you can win a series: Game 7 vs. Boston in 2018, Games 6 and 7 vs. Boston in 2019, Game 5 vs. Columbus in 2020, Games 5, 6 and 7 against Montreal in 2021, Games 6 and 7 vs. Tampa in 2022, Games 5 and 6 vs. Tampa in 2023, and Game 7 vs. Boston this year. In those 12 games, Matthews has five goals and five assists, Marner four assists, Nylander two goals and seven assists, and Tavares four goals and two assists in eight of those games. The Leafs drafted and built around elite players; they haven’t proven to be elite enough playoff players, together.

By the time Dubas finally decided the core could not continue forward together — and according to sources, he made that clear before he left, even publicly musing about a Matthew Tkachuk-style trade — it was too late. After Dubas’ power move gone wrong, the organization paused to reset: Marner’s no-move kicked in, Nylander’s trade protection expanded, Nylander and Matthews got no-moves in their extensions and the window to easily change course was closed.

So new general manager Brad Treliving added a mixed bag of contracts, the team met Boston in the first round and in Game 4, down 2-1 in the series, the Leafs looked as lost as they did for that long stretch in Game 6 against Boston in 2019, or in Game 7 vs. Montreal in 2021, or in parts of Game 3 against Florida in 2023. Demons, maybe. Ghosts. Or, just as likely, a poorly built team exposed for what it is.

pc28����lost in overtime of Game 7, Keefe was fired, Berube was hired as an accountability and expectations coach, and here we are. Maybe the organization didn’t ask for enough from the core: not from a GM who texted collegially with his players, not with a coach who criticized them publicly and had to back away. Maybe they never built a culture the way winning teams did. When Schenn came to the Leafs, one of the things he noticed was the team tended to only eat team meals in the hotel. They didn’t go out to dinner together, bond together.��

And when Schenn and O’Reilly declined to re-sign with Toronto, one thing they both told friends was that the organization’s country-club atmosphere was not what they were looking for.

The Leafs have now gone from league royalty in Lou Lamoriello and Babcock to league rookies in Dubas and Keefe to league retreads in Treliving and Berube. Maybe a big trade is coming, or maybe another attempt with this group. Maybe it works. It could happen.

But the demons aren’t gone, and franchise-altering decisions still loom. At the end of that Amazon series, after the failure had become evident, Keefe told the camera: “Just because you haven’t won doesn’t mean you cannot or will not win.” It might, though. It did. It has.

Fans such as Powell can only shake their heads and decide who gets the most blame. There are historical bad guys such as Harold Ballard, the franchise’s one-time miserly owner, and his money-grubbing descendants at the Ontario Teachers’ Pension Plan. But Ballard died in 1990. The pension plan sold to Bell and Rogers in 2012.

When Powell looks at the disappointments of the past decade, he points the finger at two people in particular. There’s Shanahan, who has been unable to take the combination of skill and toughness that made him a hall of fame player and infuse it into his team.

“I’m at the point, I’ve given up on Shanahan doing anything,” Powell said.

Dubas, of course, is the other.

“I’m embarrassed to say I’m a graduate of Brock University, because so is Dubas,” Powell said. “Dubas destroyed this team. But then again, who let him? Shanahan let him.”

He knows what to count on, though. Like the passing of the seasons, Powell knows the Leafs will raise their prices, and they will let him down. Those first-row greens where he sat in 1967 have been in his family for 75 years and will get more expensive next season — up to $13,800 from $13,400 for the pair.

“It’s year after year, season after season. It’s frustration after frustration,” Powell said. “To reach this stage, my god. Who would have dreamt we’d go from 1967 to 2024 and not have a sniff, basically?”

There have surely been worse times in Leafs history, but the current situation is perhaps even more frustrating. So much potential, so few results, and promises unkept by executives with no track record of building anything.

“We are in a crisis. For people like me who are getting up there in age, and there’s a (lot) of us, it’s a crisis,” Powell said. “How the malaise that has overcome the Leafs organization can be allowed to continue is beyond me. It just cannot continue … For me, as a fan, it’s been a good ride. But if it ended now, it would end on a sour note.

“I’m running out of time. Once you hit 80, you don’t know how many more seasons you’ve got left.”

Correction — July 8, 2024

This story has been updated. Clarence Campbell was NHL president, not commissioner, as incorrectly stated in a previous version of this story.