15. That hurts
March 11, 2000
Yes, every team has injuries and champions distinguish themselves by how they overcome such setbacks, not by making excuses.
But as a team rarely blessed by depth since 1967, injuries at any point in the season took an especially high toll on the Leafs.
In 1978, during an improbable run to the semifinals, they managed to get past the New York Islanders without all-star defenceman Borje Salming, out with an eye injury.
But there was only so much Ian Turnbull and the rest could accomplish, especially when the Leafs ran into the stacked Montreal Canadiens in the next round.
Some 15 years later, and in the Cup semifinal again, a gaunt Doug Gilmour barely made it through 21 playoff games in 42 days and, though not actually hurt in one specific body part, this depleted bag of bones had little in the tank for Game 7 against the L.A. Kings.
Back in the conference final the next year, Gilmour was playing on a bum ankle and top defenceman Dave Ellett recovering from a separated shoulder when the Leafs couldn't get past the Canucks.
The irony is that in 2002, with several players on the shelf with injuries -- including top scorer Mats Sundin and energy wingers Darcy Tucker, Tie Domi and Garry Valk -- the Leafs went deep into the playoffs, only to falter once the banged-up players returned and eager farmhands were taken out of the lineup.
But the Leafs have had their share of training-camp and regular-season mishaps, too. From the 1980s on, there were severe injuries to first picks such as Craig Muni, Gary Nylund and, early in their careers, Wendel Clark and Al Iafrate.
In the late '90s and early '00s, the bad luck of the high picks continued when Luca Cereda and Karel Pilar developed career-threatening heart problems and Nik Antropov and Carlo Colaiacovo were shelved by a series of health mishaps.
Eye injuries have also been prevalent, affecting the career of Bryan Berard, who was hurt on this date, and ending that of minor-league prospect Mark Deyell.
Gilmour's Leafs and NHL career would end with him being helped off the ice in Calgary with a knee injury.
14. Divorce and Dave Keon
April 19, 1975
"He was a Leaf through and through and the way he was treated at the end cut him to the bone."
So said a teammate of Dave Keon's, who along with Mats Sundin were considered the best Leafs never to have captained a Cup winner.
Recently voted the greatest Leaf of all time by a hockey panel selecting the top 100 Toronto players in team history, the first captain of the Harold Ballard era was deemed to be lacking leadership in the eyes of the owner. That was despite being close to a 40-goal man in his early 30s and still doing all the little things, such as winning faceoffs and killing penalties, that had made him a big part of four Cups in the 1960s.
But asking for a salary consistent with his value and a no-trade clause -- both deserved to make up for being underpaid in the team's glory years -- was the issue that drove Keon from the team and later convinced him to sever all connections. He should have been given the chance to properly guide Darryl Sittler and the '70s Leafs towards a new Cup chapter. But he was gone in the summer of '75, after playing his last game on this date.
Ballard made a bluff offer for Keon to make his own deal elsewhere, then set the compensation bar so high that no other club touched him. Keon did an end run and signed with the WHA, with his attempt to come back as a checker with the Cup-bound New York Islanders again thwarted by the Leafs, who held tight to his NHL rights.
He returned to play the Leafs at the Gardens one last time in the early '80s with the Hartford Whalers, but from the moment he retired, he vowed not to re-enter the building for any Leafs-sponsored event.
He was further outraged by the team policy of keeping the sweater numbers of Leafs greats in circulation, rather than retiring them as was the norm in the NHL. He also detested the way Ballard had the Smythe family written out of team history.
Keon's grudge and boycott extended to new ownership's attempts to honour him, though he relented just once (at left) to be with his teammates for the 40th anniversary of the '67 Cup. He was given a standing ovation, but not the longer and louder tribute that was expected, partly because the exile made him a stranger to the younger generation of Toronto fans, a man they only knew from black-and-white newsreels.
"He had differing opinions and stuck to them, so you have to admire him for that," Johnny Bower said.
He had so much more to give as a player and a mentor, yet No. 14 remains a missing ingredient to a title.
13. Ballad of Mats Sundin
Dec. 18, 2008
He was the leading points producer in team history and professed his love for the city.
Yet, both sides had strange ways of expressing their commitment to each other and, in the end, neither side got what it wanted most. Mats Sundin had no Cup for 13 seasons of hard work and the fans never gave 100% of their hearts to him.
Many griped that, for all the years he led the Leafs in scoring, he could never lead them in the field when it counted, a key critique of the trade for Sundin that had cost Wendel Clark.
And though Sundin never said it publicly, there were years when the Leafs let him down, unable to surround him with wingers who could bury the great passes he was laying in the slot or add the pieces needed to put the Leafs over the top.
Sundin's oft-stated desire to be a Leaf for life ended with a one-year contract for 2007-08 that underlined how the relationship had gone south.
He took a wait-and-see approach, to judge if the 2008-09 Leafs were going to be a good fit for him and if he even wanted to play.
That decision became a drawn-out affair that saw Sundin hang on to his no-trade clause as an influential ringleader of the so-called Muskoka Five in the spring of '08. The Leafs ended up receiving nothing in return and the distracting guessing game almost carried into the calendar year 2009 before he finally chose to play a bit role with Vancouver.
Sundin is now retired and the search for the next captain and franchise player goes on.
12. Gutted by Rollie the Goalie
May 23, 1999
Word quickly filtered through the Air Canada Centre on this rare afternoon playoff game that Sabres had gift-wrapped Game 1 of the Eastern final by not starting their ace goalie, Hart Trophy nominee Dominik Hasek.
The Dominator, who was either hampered by a groin injury or embroiled in one of his frequent flare-ups with factions on his own team, was not in the crease for the national anthem, replaced by Dwayne Roloson. To this date in the playoffs, Curtis Joseph had been hot, getting the Leafs to the conference final in 12 games, with 25 goals allowed. Roloson had never won a playoff game.
But the Leafs were not sharp on this day -- too pretty with their passes according to coach Pat Quinn -- and lost the opener 5-4.
Though they got to Roloson the next game, the Sabres achieved the split they needed on the road and Hasek magically returned in top form and gave up just six goals in the final three games.
A golden chance had slipped away.
11. Gretzky arrives at the Gardens
Nov. 21, 1979
The NHL's icons always seemed to shine at Maple Leaf Gardens and the Air Canada Centre, in games usually broadcast coast-to-coast. But starting with his first NHL appearance in front of family and friends from Brantford, hurting the Leafs at home was raised to painful levels by No. 99.
Within two games at the Gardens, the Edmonton Oilers wunderkind racked up 10 points, then 20 goals and 20 assists after 11 starts. At one stage, he was averaging 1.48 goals a night at MLG and .86 as a visitor everywhere else. The final dagger was virtuoso performance in Game 7 of the '93 conference final.
"I love playing there," Gretzky said. "It's a great building with so much tradition."
As Gretzky went, so did fellow 1980s and '90s stars Brett Hull, Eric Lindros and Mario Lemieux, all fattening their career numbers at the Leafs' expense, home and away.
When the Air Canada Centre opened, a new galaxy of stars such as Daniel Alfredsson, Dany Heatley, Ryan Miller, Sidney Crosby, Alex Ovechkin and Ilya Kovalchuk began using the big stage to beat up on the Leafs.
Only a select group of Leafs ever enjoyed such a comfort zone.
10. Expanding NHL swallows Leafs
Oct. 25, 1967
The Leafs have pocketed millions in expansion fees since 1967-68, but they don't seem to be spending it on Stanley Cup parades.
Since they ushered out the Original Six era with their '67 Cup and played their first expansion team, the L.A. Kings, on this date, the Leafs have seen 15 other teams drink from the mug.
That includes every one of the old guard except the Chicago Blackhawks, meaning 11 teams that began life as a piece of paper and pen, went from scratch to beating the Leafs to the title. Yet, a parade of GMs in the past two decades has boldly proclaimed the Leafs are no expansion club and that sophisticated Toronto fans shouldn't have to sit through a three or five-year rebuild.
But in some cases, clubs such as the Pittsburgh Penguins have won the Cup, bottomed out, were sold and came back to win it again while Toronto spun its big wheels. Eight other teams, including Canadian rivals Ottawa and Vancouver at least made the final, which the Leafs haven't reached since '67, either.