Time flies. Especially when you're losing.

The Toronto Maple Leafs will host the Detroit Red Wings outdoors on Sunday afternoon, New Year's Day, in the seminal event of their centennial season year-long celebration. So there's no better time than to look back, and look forward.

Legacy of defeat

By now, you know: 13 Stanley Cups. None since 1967. The facts are the facts - the Maple Leafs have only ever known victory in a six-team NHL.

There will be 31 in 2017.

So there's no point in looking back on the first 50 years. They were good. Hell, grand. But it was a different NHL, a different hockey world. It's the last 50 years that have come to define Toronto's hockey team.

Darkness

You can break down the Maple Leafs by players by era, and one who approaches life with a glass-half full approach would say, post-1967, the blue and white belonged to Darryl Sittler (drafted in 1970) and Borje Salming (debuted in 1973). A more pessimistic, defeatist person would go with Harold Ballard, who owned the team from 1972 until his death in 1990.

Either way, the legacy of those years is the same: losing.

The longest playoff runs of Sittler's and Salming's careers as Maple Leafs were 13 games.

From 1967-68 through 1991-92, the Maple Leafs won 40 games in a season only once. They won just eight of 24 playoff series, getting swept in the spring seven times. And even those numbers are deceiving: seven of those 24 postseason appearances came with losing regular-season records. In 1985-86, Toronto went 25-48-7, but won its first-round series. They made it to the second round in 1986-87 after a 32-42-6 season.

A lost generation.

Eye of the storm

It hasn't been all bad. Mostly bad, but there were some good years. Great, even. The Wendel Clark, Doug Gilmour, and Mats Sundin years. Let's call them respites. Short and sweet.

These years were defined by key people and key moments.

Clark's arrival, Cliff Fletcher's, Pat Burns', Gilmour's 127-point 1992-93 season. The Conference Finals runs in '93 - Wayne Gretzky's high stick in Game 6, and his otherworldly Game 7 - and 1994. Clark for Sundin, another trade that shook Toronto.

Ken Dryden's arrival, Pat Quinn's, Curtis Joseph's, Alexander Mogilny's. In Sundin's prime, from 1998 through 2004, Toronto won 40 or more games in five of six seasons, 45 in three of them. Four straight playoff wins against the Ottawa Senators - for many Leafs supporters, their Stanley Cup. More deep playoff runs.

But in the end, Sittler, Salming, Clark, Gilmour, and Sundin - the greatest Leaf of all time - all made it to the same place and no further. Forget about winning a Stanley Cup, Toronto hasn't played for one since '67. In the end, Leafs fandom remains one that ends in heartbreak.

Hell

The years after the 2004-05 lockout are ones Maple Leafs supporters try only to forget. No goaltending. No penalty kill. After Sundin, no one down the middle.

Enter Dion Phaneuf, arguably the worst captain in Maple Leafs history. He tried. And Brian Burke, the most impatient GM in Maple Leafs history.

Don't forget Phil Kessel, acquired for two first-round picks, he tried, too, but it was never good enough.

Only one playoff series to show for it all, one that ended in the most Maple Leafs way possible, Game 7 in Boston. Yes, it was indeed 4-1. It's a badge of disturbing honor.

The plan

Brendan Shanahan was hired in 2014. He brought with him, finally, a plan. A tear down in every meaningful sense of the word, the organization stripped and put back together. A true rebuild. And, already, it's working.

Toronto, with Mike Babcock behind the bench, bottomed out - and this time it had its first-round pick. For the first time since 1985, when Wendel Clark's name was announced first overall, the Maple Leafs would draft No. 1.

The ping-pong balls, literal and figurative, never bounced Toronto's way. Until now.

Light

Auston Matthews is a Maple Leafs rookie like no other.

And yet he's already surrounded by those who will help him do what no other Maple Leafs team has done since the NHL expanded 50 years ago.

William Nylander. Mitch Marner. Local boy Connor Brown. A goalie in Frederik Andersen. Morgan Rielly. Nazem Kadri. Point-per-game AHLers in Brendan Leipsic and Kasperi Kapanen. A core.

The Maple Leafs are building something. The system has never been so full of young talent. The organization has never been so competent. That it's coming together so quickly, far quicker than anyone anticipated, in the club's centennial season, makes one wonder if this - a committed rebuild, a plan - is all it took.

Could it have been so simple, all along?

No, probably not. And there likely will be more bumps along the way. But that's the point - the Maple Leafs are on their way, traveling somewhere, as opposed to spinning their wheels, trying anything, desperately, to get out of the ditch.

So much of life comes down to timing, and after 50 years, it appears a broken clock is ticking once again.

As Toronto prepares to host its first outdoor NHL game, this incarnation of Maple Leafs is playing its best hockey, so you can forgive the club's supporters for thinking big, for dreaming.

That's what celebrations are for, after all.

Playoffs? Sure, why not.

Consider it practice. There are even bigger things in store.

As the Maple Leafs turn 100, it's more a rebirth than a 100th birthday. Years from now, perhaps the Centennial Classic will be looked upon as the beginning.

Shanahan, Babcock, and Matthews came along when one of hockey's most iconic franchises needed them most. The timing, for once, seems good.

Here's to the next 100 years - but especially the next 10.

Copyright © 2016 Score Media Ventures Inc. All rights reserved. Certain content reproduced under license.