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The most crushing Leaf playoff defeats in my lifetime….

Today I want to get away from the contract soap opera stuff hanging over the Leafs and talk about something a little different.  And I don't mean former Maple Leaf General Manager Brian Burke, who as we all now know has become President of Hockey Operations for the recently floundering Flames.  

So with training camp (well almost; rookie camp, at least) here, it seems like a safe  time of the year to raise today's old-time memory, when we Leaf supporters are not in the midst of that right-on-the-surface emotion of NHL playoff hockey.  Let me explain.

When we cheer for a particular team, there are certain games that, when we look back, really stand out in our memory.  They just do.  It can be for good reasons, or it can be because we were so disappointed and heartbroken that the team we have a deep rooting interest in lost.

Now when it comes to the Maple Leafs, well, we all know that the Leafs have lost plenty over the years.  They certainly have since I became a follower of this franchise back in the late 1950s- most notably, of course, since 1967. (But hey, the early '60s were pretty sweet for Leaf followers- at least those of us who were around at the time!)  But what I’m talking about today are those games, especially at playoff time, that hurt more than others—games that, if I stop and think about them, still sting to this very day.

For today, I’ll focus on five games throughout my history following the club that stick out in a singularly painful way.  (This is more chronological order than necessarily which game was most upsetting…)

1965 semi-finals, Game 6 versus Montreal

In the early spring of 1965, the Leafs were gunning for their four consecutive Stanley Cup.  (If you’re a young Leaf fan, you may not be able to quite imagine that.)  They were life and death to beat the Red Wings the season before for their third Cup in a row but fortunately, they won.

They added ex-Hab great Dickie Moore (left) before the 1964-'65 season. Moore was making a comeback after a serious off-ice knee injury and a year away from the game. The Leafs also brought in netminder Terry Sawchuk (a future Hall-of-Famer), so they seemed good to go for yet another Cup run.  In fact, Johnny Bower and Sawchuk, if I remember correctly, teamed up to win the Vezina Trophy that season (in those days, that went to the goalie with the best goals-against average.  They shared it though Sawchuk played a bit more than Bower.  He actually insisted the league change the rule so Bower’s name would be on the trophy, too.)

In their semi-final series that spring against Montreal, the Leafs were trailing the Habs going into Game 6 in Toronto.  I was listening on the radio in my bedroom, because my Dad, a steadfast and highly emotional Montreal supporter was watching in the nearby den. When the game went into overtime, I slid into bed while still listening to the game.  I was so nervous.  I’ll never forget (since it was the radio, I believe it was Foster Hewitt’s voice) that sinking feeling the moment I heard Montreal had scored.  (I always get confused as to whether it was Claude Provost or Gilles Tremblay who scored, but I’m sure it was one of them.)  I was almost 12 at the time and it was such a lousy feeling.  I hated the Habs but more importantly, the Leafs were no longer champions.  That one stands out.

1971 quarter-finals against the Rangers, Game 4

I’ve written extensively here about the 1970-’71 Maple Leaf team.  It had a tremendous blend of young, eager kids and old guys with experience.  Jacques Plante and young Bernie Parent shared the net.  Bobby Baun was the godfather of an otherwise “kiddie corps” defense (Ley, Selwood, Glennie, McKenny, Pelyk, Dorey).  (That's Baun, below right, with a young Rick Ley in a great early '70s Dan Baliotti photo.)  Dave Keon and Norm Ullman (and the ageless George Armstrong) were the oldsters on a team that had up and coming players like Jim Harrison, Darryl Sittler and Brian Spencer.

After three games in the series the Leafs were, shockingly, leading the Rangers (who were a great team in those days—Park, Giacomin, Hadfield, Ratelle, Neilson, Gilbert and ex-Leafs Bob Nevin, Pete Stemkowski and Tim Horton) two games to one.  But after a big win on Saturday night at Maple Leaf Gardens in Game 3, Toronto had to play right away the next night at home.  They never played on Sundays at the Gardens back then and they stunk out the joint.  I’ve always felt they would have benefited from an off-day between games.  It was 4-0 before you knew it and that was pretty much the game.  The Leafs never recovered, though they later took Game 6 to overtime.

I loved that particular Leaf squad and really thought an upset was in the making.  But Game 4 let the air out of my balloon- and theirs.

1977 quarter-finals against Philadelphia Game 3

That spring in the playoffs, we were playing a still rough and tumble (and talented) Flyer side that had won the Cup twice just a few years earlier.  The Leafs beat the Flyers right at the Spectrum in the first two games of the series.  We had tough guys like Kurt Walker and Scott Garland on that team, along with our stars like Sittler, Salming,  Palmateer, Turnbull, McDonald and Tiger Williams, etc..

Right after Game 2 in Philadelphia was when Tiger uttered the famous phrase (on national television) that the Flyers were “done like dinner”.

Apparently not.

In Game three (I was at that game), the Leafs jumped out to a 2-0 lead at home. The Flyers were totally out of sorts.  But Philly eventually chipped away to tie the score.  Just when the Leafs looked like they were out of gas mid-way through the third period, Errol Thompson scored on a quick backhander, somewhat against the run of play, as they say in soccer.  It looked like his goal would stand up, but a Borje Salming clearing attempt did not get out of the zone in the last minute, and Bobby Clarke was relentless until the Flyers tied the game.  They won in OT and then the same thing happened in Game 4 at the Gardens. The Leafs were, well, done like dinner.

1993 semi-finals against the Kings Game 6 (and 7)

Do I really need to say much?  Those of you who were around at the time well remember what happened.  Leading the series three games to two, the Leafs were trailing the Kings in Game 6 at the old LA Forum.  But Wendel Clark played one of the games of his life and triggered a Leaf comeback.  Then the ref missed the Gretzky high stick on Gilmour.  Instead of being tossed from the game, Gretzky ended up scoring the winner in overtime.

Game 7 was like climbing a hill you were never going to get up.  The Leafs played their hearts out but the Kings won that one, too.  (Bob Mackenzie, then with the Toronto Star, wrote before Game 6 that Gretzky had been playing like he had a piano on his back.  He sure didn't after that...)  Depression is too serious a word to throw around lightly, but strictly in the fan/hockey sense, the outcome of that series was depressing.  Numbing, in fact.  It felt like the everyone in the city of Toronto was walking around in a daze the next day. It still feels like we were somehow cheated.

It would have been a Montreal-Toronto final.  Oh well.  It's good that I don't hang on to things, eh?

2002 semi-finals against Carolina, Game 6

If ever there was a year I thought we would get to the finals, it was in the spring of 2002.  We had a very strong team (imagine, as I noted the other day, if we had still had a healthy Bryan Berard) and bulled our way into round three, with Cujo in net.  And lucky for us, we drew the Carolina Hurricanes—the Carolina Hurricanes.  I mean, they had some nice players and everything but c’mon.

Lo and behold the Canes were somehow leading the series three games to two before Game 6 in Toronto.  (They had home ice advantage because they finished first in the “Little Sisters of the Poor” division or whatever it was called back then, though the Leafs had more points in the regular season.)  Just when we looked like toast, Mats Sundin (left) scored with second left in regulation time to send the game into extra time.

Then, in overtime, the uber-talented but ever frustrating Alex Mogilny, rather than clearing the zone when he had the puck on his stick near the side boards in his own end, inexplicably threw it back behind his own net, whereupon the Hurricanes pounced on it. The puck was in the net before I could yell at Sir Alex from my chair.

As Mogilny said (this may not be an exact quote, but pretty darn close) after the game, when asked why he passed the puck to nowhere in particular: “I had to put it somewhere”. OK.  Now we understand.

Five games.  Five losses.  Five excruciatingly painful memories.  Five playoffs series I felt (hoped?) would end differently.  And I haven’t even included the Game 7 loss against the Bruins this past May.  I know from chatting with people here at VLM that that loss has stayed with a lot of Leaf fans a long time.

Part of this exercise for me is sharing the pain—so by all means share your own memories of painful playoff Leaf losses…


  1. This past year, I really believed in the mix of veteran depth and speed at forward, (Kessel, Grabbo, Lupul, MacArthur, Kulemin and McClement) and Marlie kids (Kadri, Frattin, Fraser, and Colborne .) I thought they could get into the first and scare a good team and I was proven mostly right.

    I was crushed with the 7th game loss. I felt we could have gotten to the third round, but for a few minutes.

    I couldn't watch hockey again for weeks and could only watch the final with the hope that Chicago would get me some revenge.

    When they Boston collapsed and Chicago won, all seemed right again, and I could finally get on with life.

    1. You weren't alone, DP, in experiencing a hockey hangover after the Leaf-Boston series. It was there for the Leafs, and it just didn't happen. Very tough.

    2. A vastly more talented group of prospects than 5 years ago. We are becoming a respectable organization:|TOR|home

  2. May 2004, Game #6. Jeremy Roenik. That wouldve been us going up against the Tampa Bay Lightening, whether we would have won that series or not, I still remember being excited about winning game 6 after forcing OT and having no problems with winning game 7. To this day I still remember that shot, after Tucker had just gave Kapenen the case of spaghetti legs, Roenik comes down on the left side, top of the faceoff circle, top corner glove side on Eddy.

    1. That game certainly deserves to be on the modern-day list, Anon! Thanks.

  3. I suppose that each person's opinion here is heavily mitigated by their age. As much as I like to think I'm a decent historian on the Leafs, it's impossible for me to feel too much about hearbreaking losses and chokes before 1980, and of course there wasn't exactly a heavy playoff atmosphere around for a while after that. So for me it has to be the 1993 semi-finals.

    It was a tough time for me personally, having just lost my mother, and boy were the Leafs a wonderful distraction for me during the month of May. As they wound their way through the playoffs I began to believe more with each victory that this might finally be their year. I'll never forget the image of Wendel Clark going toe to toe with McSorley after his cheap shot on Gilmour, and I will never forget Pat Burns' declaration after the game that the Leafs "would have been hung on Parliament Hill" had they done the same thing to Gretzky. But the tone was set, it was a great series, and I really thought they had it won once they went up 3-2. Alas the rest is history.

    This past year's collapse will hang in the air for a while, but in the long run it won't sting as much, as the Leafs were never expected to take the Bruins so far in the first place, and no one thought them a serious contender, so as much as it may be the freshest in our minds, once the puck drops this year I think most Leafs fans will move on from that one. 1993, however, I still cringe when I think the Leafs should have been in the finals.

    1. Great post. Thanks Pete. You note beautifully how, as in the case of the passing of your mom, sports can indeed be a healthy distraction.

      '93 may have been the worst moment for many modern-day Leaf fans, given what lie ahead of us at the time: a rematch of the '67 Cup finals with the hated Habs. Thanks Pete.

  4. Game six in 2000 was pretty crushing, sitting through as they put up six shots (I think there were probably a couple more) against the Devils at the height of the dead puck era.

    As for non-playoff, a game against Carolina on Nov. 19/09 sticks out for me. The Leafs were off to an abysmal start and the Hurricanes were stuck at the bottom of the conference as well, with 34 seconds to go Ian White scored to go up 5-4 and it looked like they might get a little confidence together. Then they blew the lead with 3 seconds left, and lost in a shootout. That was as deflated as I can remember feeling through the no playoff years.

    I don't get why you'd find Mogilny frustrating. He was the most exciting Leaf on the ice for his entire tenure in TO and always hilariously sarcastic to reporters. We were so, so lucky to have him.

    1. The six-shot playoff game was tough, for sure, Grabovski.

      I just felt differently about Mogilny, I guess. I thought he was a gifted player, obviously. But he would disappear too often. While I admired his talent, I didn't personally see him as exciting by the time he hit Toronto. His early years, yes. Thanks for posting.

  5. I still cannot watch the replay/review/highlights collapse in Boston.

    1. Then watch this... (CRANK THE VOLUME)

      The lowlights are there but it's done quite well and more hopeful than painful. Like a mini sports doc.

  6. I share the pain of all but your first recollection. Though I didn't expect much against the talent-laden Rangers in '71, I was beginning to believe we had the tiger by the tail with such an impressive start against the '77 Flyers, yet given the (yet early) Game 3 loss, the writing was on the wall as the series progressed and hopes faded as the losses piled up and our early hopes were squashed 'more slowly' than later iterations.

    I have mentioned before that just prior to Gilmour's arrival, I was at my lowest ebb as a Leaf fan, so the '93 series was easily the hardest to endure. I think the hope of a Habs final bleeding out (like Dougie's face) in such an unjust scenario (losing at the hand/stick of the one who carved his own final appearance out of Leaf flesh!) was almost beyond belief. Amongst 'the agony of defeat(s)' this ranks poignantly high, especially for all of us.

    The Carolina loss was just 'boggling' for me... it seemed like it just shouldn't have happened, but was not as severe as '93 (perhaps I was numb).

    I don't think any game was more frustratingly devoid of any redeeming qualities than the 6-shot game against the Devils that Grabovski mentioned. And although I think 'getting past the Bruins' could have led to further success, the loss will not stay with me anywhere near as long as '93 (yet I understand how younger fans will feel about the matter). Hopefully, we're just trending upwards to a more glorious future once more!

  7. You've laid it out perfectly, as usual, InTimeFor62. '93 was just so....disheartening. '02 was maybe a shock, in the sense that some of us expected we would simply go further. But it's never simple, I guess!