The Toronto Maple Leafs have had many struggles since last winning the Stanley Cup in 1967.
There are nine teams that have joined the league within the past 25 years, starting with the San Jose Sharks in 1991-92. The other 21 teams have been playing for the last 25 years and 14 of them won the Stanley Cup in that time frame.
Two other teams, the Philadelphia Flyers and Vancouver Canucks, have been consistent playoff performers and have come close but failed to win the Stanley Cup.
Both teams have been successful.
The remaining five teams have failed to win the Stanley Cup or much of anything in the last quarter century. That qualifies them as the five least successful franchises of the last 25 years.
The New York Islanders were the lords of the domain in the early 1980s.
They followed the Montreal Canadiens' superlative dynasty of the late 1970s with one of their own. Starting in 1980 with a six-game triumph over the Philadelphia Flyers, the Islanders won four Stanley Cups in a row.
However, they have not won a Stanley Cup since that 1983 when they defeated the Edmonton Oilers in four straight games.
Beginning with the 1986-87 season, the Islanders have been wandering in the NHL's version of the desert for much of that time. They have only made the playoffs in eight times. The furthest they have gotten was reaching the conference finals in the 1992-93 season, where they lost to the eventual Stanley Cup champion Montreal Canadiens.
The Islanders were once a model franchise. Now they are fighting and clawing for respectability and they rarely achieve it.
The Capitals have made the Stanley Cup playoffs 19 times in the last 25 years. That's a very high percentage and indicative of consistency over a long period of time.
However, they have seen their season end in heartbreak too many times.
One of the worst endings came in 2009, when they appeared to have an excellent chance of representing the Eastern Conference in the Stanley Cup Finals. However, they met their hated rivals, the Pittsburgh Penguins, in the second round.
Though they battled on even terms for six games, the seventh game was no contest even though it was played in Washington. The Penguins and Sidney Crosby got the best of the Capitals and Alex Ovechkin by a 6-2 margin.
The following year, the Capitals played like a determined team all season and finished first in the Eastern Conference. Despite that lofty perch, the were beaten in the first round by the eighth-seeded Montreal Canadiens in seven games.
Since that series, the Capitals have been trying to define themselves and look for an identity that would allow them to end their Stanley Cup dry spell.
They have not come close to finding that answer.
The Toronto Maple Leafs have won 13 Stanley Cups, more than any other NHL franchise except Montreal.
Yet, the Maple Leafs have not won a championship since 1967, when a group of savvy veterans brought Lord Stanley's Cup home after defeating the Canadiens in six games
The past success the team had seems to mock the current Leaf teams—they have not made the playoffs since the 2003-04 season.
Since the last lockout wiped out the 2004-05 season, the Maple Leafs have been on the outside looking in for seven straight years.
They have been to the conference finals four times in the last 25 years, but they had their hearts broken each time.
None worse than in 1993, when they led the Los Angeles Kings three games to two, only to lose the final two games of the series. In the seventh game, Wayne Gretzky stomped on the Toronto fans' hearts by scoring a hat trick to send the Kings to the Stanley Cup Finals.
The St. Louis Blues went to the Stanley Cup Finals in each of their first three seasons.
They were champions of the Western Conference and earned the right to play against the Montreal Canadiens in 1968 and 1969 before playing the Boston Bruins in 1970.
They were swept in all three series and the loss to the Bruins featured one of hockey's most famous images, Bobby Orr's flying goal in overtime of the fourth game that gave the Bruins the triumph.
While the Blues have been frequent playoff participants—missing the playoffs only five times in the last 32 years—they have never won the Cup and haven't gotten back to the Finals since 1970.
Despite having a number of great players like Brett Hull and Adam Oates and some solid seasons, the Blues have known quite a bit of heartbreak and despair over the last quarter century.
The Phoenix Coyotes had a memorable 2010-11 season. Not only did they make the playoffs, but they also defeated the Chicago Blackhawks and Nashville Predators in the first two rounds to make it to the Western Conference Finals.
While they were beaten by the eventual champion Los Angeles Kings, it marked the most success the Coyotes franchise had enjoyed in an NHL postseason in their history.
Prior to winning those two series, the only time the franchise had won an NHL playoff series came in 1984-85 when the Winnipeg Jets beat the Calgary Flames in a first-round playoff series.
Those Jets moved to Phoenix prior to the 1996-97 season.
Not only have the Coyotes struggled to find success in the postseason, but they have also had significant off-the-ice issues and they are commonly mentioned as one of the least stable franchises in the NHL.