Original 6. 

Three straight championships.

13 Stanley Cups.

The Toronto Maple Leafs used to be a powerhouse, a team that made other players tremble in their skates. But now they’ve only made the playoffs once in the last five seasons. It’s been 48 years since the Leafs have raised a Cup, the longest championship drought in the NHL. So how did this former dream team end up at the scavenging for crumbs at bottom of the Eastern Conference?

Looking back on the team that went from serious champions to the butt of almost every Eastern Conference joke, it’s easy to see that inconsistent management and coaching, bad trades and not being able to negotiate and keep their players happy led to their downfall.

The drama is so heavy with these guys that they may want to give up hockey and start their own soap opera.

From 1962 to 1964 the Maple Leafs had it all. Left winger Frank Mahovlich led the team to three back-to-back Stanley Cups championships, and then grabbed another one for them in 1967. Mahovlich was a star, but eventually the team couldn’t give him what he wanted. It’s reported that he was so disgusted with the offer they presented him with in 1968 that he walked out of training camp and went with a trade to the Red Wings with Pete Stemkowski and Garry Unger.

Things only got worse in the 1970s, when owner Harold Ballard made a series of trades and hires that hurled the team down a slippery slope towards the bottom. Lanny McDonald and Darryl Sittler, two players fundamental to Leafs success, were traded under unfriendly circumstances, and the team truly suffered, barely making an entertaining performance for almost 12 years.

The 1990s saw a glimmer of hope for the Maple Leafs, when new GM Cliff Fletcher came over from the Calgary Flames to help rebuild the team. Rebuilding can be a scary notion that can either make or break the team, but fortunately Fletcher was on the right track. The Leafs finished the 1992-1993 season with 99 points, and powered through the first two rounds of the Stanley Cup Playoffs, only to lose to the Los Angeles Kings and the Almighty Gretzky in the Conference Finals.

Unfortunately, more shifts in management and key players lost to trades forbade the Leafs from keeping up their growing stamina. In 2005 the team missed the playoffs for the first time since 1998, and it’s been a downward spiral since. In 2008, they fired their General Manager John Ferguson, Jr. mid-season and center Mats Sundin, whose contract was due to expire at the end of the season, refused to waive his no-trade clause. The Leafs were helpless as his contract ran out and Sundin left for the Vancouver Canucks as a free agent. Toronto was unable to replace him through trade with fresh, young players.

Probably the most notable mistake of recent times is the infamous Phil Kessel trade. The Leafs were probably certain they were getting a great deal of trading their first- and second-round 2010 picks and 2011 first-round draft picks to the Boston Bruins in exchange for right winger Kessel. Little did they know they were missing out on the breakout rookie that was Tyler Seguin, who this season ranks in third in the league for points. Kessel had a total of 446 points in six seasons with the Maple Leafs, leading them to the playoffs only once, before being traded to the Pittsburgh Penguins in 2015.

So is there a light at the end of the maple-scented tunnel for Toronto?

It’s hard to say. With the right trades, drafts, and developments, any team can turn around at any time. But the questions remains if Toronto has what it takes to dig themselves out of the hole they’ve been consistently burying themselves in since their last Stanley Cup win in 1976. They’ve had some big wins this season, annihilating Tyler Seguin and the Dallas Stars 4-1 in Toronto and then again 3-2 back in Dallas. But a couple of good games isn’t going to pitch a 9-13-5 team into the playoffs from the bottom of the conference. Unfortunately for Toronto, only time will tell if they’re meant to once again be the heroes of the Eastern Conference.

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