TORONTO – Brendan Shanahan was at a hospital fundraiser last week and heard one of the other dignitaries in attendance suggest that the Maple Leafs were finally in position to win a Stanley Cup during his lifetime.

That’s when Toronto mayor John Tory stepped in.

“I corrected him and said that the Toronto Maple Leafs were going to win the Stanley Cup within the period of time that I am the mayor,” Tory recalled Tuesday. “I hope I’ll get a second term (in office), so that means you have five years.

“But I know – I know it’s going to happen.”

On this issue, the mayor seems to be aligned with a healthy majority of his electorate. This Leafs season is arriving with more optimism and excitement than any other in a decade, if not longer.

It’s a strange spot for Shanahan, who started from the bottom and is suddenly here.

The team president is paid not to stray from the process. It’s been less than 30 months since he embarked on a patient teardown project that became known as the “Shanaplan.” He saw the same promise as everyone else last season, but seems to have interpreted it a little differently than many around him.

“I’m a little hesitant,” said Shanahan. “At the end of the day we got into the playoffs in our 81st game, we didn’t get past the first round and yet still there was a lot of happiness and joy and optimism about where we can go.

“You know, you have to do it, and we understand that there’s a lot of work ahead of us.”

Prime Time Sports Leafs President Brendan Shanahan on being ahead of schedule September 12 2017 Your browser does not support the audio element.



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It could make for a strange season ahead. Success rarely comes without a few bumps along the way, and there weren’t many to speak of for Auston Matthews and Co. during their first spin around the NHL.

The Leafs will be turned over even more to that young core in the weeks ahead – both literally and figuratively – with the organization unveiling plans for a Dec. 19 meeting against Carolina dubbed the “Next Century Game.”

It will be played at 2 p.m. ET on a Tuesday afternoon – exactly 100 years from the debut of the Toronto Arenas. Replicas of the original blue sweaters are slated to be worn by the home side.

The occasion will also serve as an opportunity to turn the page on the organization’s centennial season and place the focus back on a group expected to deliver a bright future. As Shanahan and Tory spoke about the game in front of a group of schoolkids on Tuesday afternoon, the mayor remarked: “We’ve got a good feeling about the team.”

This is the new reality for a group scheduled to report for medicals on Thursday morning.

You can be sure the players have heard the same types of things as Shanahan these last few weeks. Most of them have been back in the city for a couple weeks at least now and are pretty plugged in on social media.

The expectations themselves aren’t the issue as much as what happens at points where things veer off-course. When the excitement is replaced by frustration. When the storylines turn negative.

As much as things have changed, this remains an organization that hasn’t won a playoff series since 2004 or a Stanley Cup since 1967. In the eyes of Shanahan, they’re still trying to win back a lost generation of fans.

“Now there’s thousands of channels, kids have choices (and) different ways to watch games,” he said. “And so there’s a generation of young hockey fans that maybe are wearing Penguin hats or Chicago Blackhawks hats or L.A. Kings hats and that wouldn’t have happened in Toronto a couple decades ago. You have to earn that back and I think that’s something our team and our players are committed to doing.

“It’s not something that we’re entitled to; it’s something that we want to earn back. That love and passion from this city.”

They began to see some overwhelmingly positive returns during a first-round series with Washington last spring. Thousands packed Maple Leaf Square outside Air Canada Centre and created a frenzied atmosphere around three home dates against the Capitals.

That’s the sort of thing Shanahan had in mind back in April 2015 when he spoke of building a team full of players willing to embrace the positive aspects of being here.

“I think that our fans like our players and I think our players like our fans,” said Shanahan. “(The players) enjoy being Maple Leafs, they love what’s happening in the city. But they’re also smart enough to know – which is incredible because it’s still a very young, inexperienced team – they seem to understand that they are just getting started.”