The rollercoaster journey of the Toronto Maple Leafs’ unsuccessful Stanley Cup quest

May 2, 1967: The Toronto Maple Leafs won their 13th Stanley Cup in franchise history, beating the Montreal Canadiens in six games. With expansion on the horizon, the future is unknown, not just for the Leafs but for the whole league. Regardless, I’m sure the Leafs will continue their winning ways… right?

The following season, the Leafs finished with a 33–31–10 record and missed the playoffs. In 1969, they’d make it back to the playoffs, but would lose to the Boston Bruins in the first round. In 1972, team owner Harold Ballard was found guilty of 48 counts of tax fraud. He was sentenced to three years in prison.

After three consecutive second-round exits, the Leafs made the conference finals in 1978, led by future Hall of Famer, Swedish defenceman Borje Salming, who had 76 points in 80 games. It was the Leafs’ best season in a decade, but sadly, they’d get swept by the Montreal Canadiens in the Conference Finals.

Throughout the 1970s, two popular professional hockey leagues existed: the NHL and the World Hockey Association. Players went to the WHA primarily due to the promise of higher salaries and the ability to negotiate their contracts. However, a merger between the NHL and WHA was made official on June 22, 1979.

The trade

In December of 1979, Leafs General Manager Punch Imlach traded Lanny McDonald and Joel Quenneville to the Colorado Rockies. This was an attempt to undermine Leafs captain Darryl Sittler.

Sittler would be traded to the Philadelphia Flyers in 1982, after a long-standing feud with Ballard. Sittler spent three seasons in Philadelphia, scoring 84 goals and 178 points during that time. He was later traded to the Detroit Red Wings, where he decided to retire after 61 games. After trading Sittler, the Leafs didn’t win a playoff series until 1986.

In 1989, the Leafs made a trade with the New Jersey Devils. This trade sent defenceman Tom Kurvers to Toronto in exchange for the Leafs’ first-round draft pick in 1991. The Devils would use that pick to draft some kid named Scott Niedermayer.

On April 11, 1990, Harold Ballard passed away at the age of 86. With new ownership on the way, perhaps the Leafs will start to prioritize winning over team revenue.

A new era

The Leafs lost in the Conference Finals back-to-back years in 1993 and 1994. Those two years were the first time the team had 40 or more wins in a season since 1978, according to Champs or Chumps.

Towards the end of the millennium, the Leafs would miss the playoffs twice and lose in the first round twice, only to return to the conference finals in 1999. They lost to the Buffalo Sabres in a five-game series.

In 2002, Swedish sensation Mats Sundin scored the biggest Leafs goal in modern memory. Sundin scored in the final minute of the third period, sending game six of the Eastern Conference Finals into overtime. The Leafs went on to lose in overtime and the series.

Fast forward two years to 2004. This would become a big year in Leafs history, as they made it to the second round. They beat the Ottawa Senators in round one to set up a second-round matchup with Philadelphia. They lost to the Flyers in six games.

Following the lockout in 2005, the Leafs missed the playoffs in 2006 by two points. They went 3–8–1 in January that season. Not only that, but they also traded one of their goalie prospects to the Boston Bruins for Andrew Raycroft. That prospect was Tuukka Rask.

The Leafs would get to know Rask very well in the future.

Missed opportunities in the draft

Brian Burke was hired as the Leafs’ general manager in 2008; he was tasked with returning the Leafs to their former glory. He traded for Phil Kessel, Joffrey Lupul, Dion Phaneuf, and Francois Beauchemin. Sure, they gave up a few draft picks, but Burke won a cup in Anaheim. He knows what he’s doing.

In 2010, the Leafs finished dead last in the Eastern Conference. A disaster of a season, that couldn’t get much worse. Except they traded their first-round pick that year to Boston in the Kessel trade. That pick was used to draft Tyler Seguin.

The next year, they finished 10th in the conference, still not where they wanted to be, but it’s a step in the right direction. They also traded their first this year, which was used by Boston to draft Dougie Hamilton.

The Leafs also traded two picks in the trade with the Anaheim Ducks. Those two picks became Rickard Rakell and John Gibson. It gets worse, in 2009, the Leafs traded for Wayne Primeau and a second-round pick from the Calgary Flames. Toronto then traded the pick to the Chicago Blackhawks to acquire their own second-round pick, which was used in the Kessel trade. The pick Chicago was given was used to pick Brandon Saad in the 2011 draft.

Choking in the playoffs

In the 2012–13 season, the Leafs finally made the playoffs again. They earn themselves a first-round matchup with the Bruins. Despite being down 3–1 in the series, the Leafs bring it back and force a Game 7. Up 4–1 with 10 minutes remaining in Game 7, it seems the Leafs will win their first playoff series in almost a decade.

They lost Game 7 5–4 in overtime, after giving up two goals in the final two minutes of the third period.

The Leafs wouldn’t make the playoffs again until 2017. Led by three young stars, Auston Matthews, Mitch Marner, and William Nylander, they’d make the playoffs every year for the next nine years. However, in that era, they only won two playoff series.

With Marner being a UFA this summer, many fans believe it’s the end of another era in Toronto. Leaving fans starving for a 14th Stanley Cup, and wondering when this “curse” will end.