Only Cup winners are allowed. Therefore, no Arizona Cardinals, no Buffalo Sabres, no Columbus Blue Jackets, no Minnesota Wild, no Nashville Predators, no Ottawa Senators (not even the old version, who went bust in 1935, before my cutoff date), no San Jose Sharks, no Vancouver Canucks, no Vegas Golden Knights, no Winnipeg Jets. Also, no WHA Champions, so, still no Jets, and no New England/Hartford Whalers, no Houston Aeros, and no Quebec Nordiques.
Seedings will be done by points, which will favor later teams that played more games. I moved the Detroit Red Wings and Toronto Maple Leafs back over into the West. And I still needed a play-in round in each Conference, because I was only able to cut it down to 24 in each, once I weeded out teams to pick out the best of the respective dynasties.
Eastern Conference
1. 1977 Montreal Canadiens, 132
2. 1973 Montreal Canadiens, 120
3. 1972 Boston Bruins, 119
4. 1982 New York Islanders, 118
5. 1975 Philadelphia Flyers, 113
6. 1994 New York Rangers, 112
7. 2006 Carolina Hurricanes, 112
8. 2017 Pittsburgh Penguins, 111
9. 2003 New Jersey Devils, 108
10. 2004 Tampa Bay Lightning, 106
11. 2018 Washington Capitals, 105
12. 1969 Montreal Canadiens, 103
13. 2011 Boston Bruins, 103
14. 1993 Montreal Canadiens, 102
15. 1956 Montreal Canadiens, 100
16. 2009 Pittsburgh Penguins, 99
17. 1960 Montreal Canadiens, 92
18. 1991 Pittsburgh Penguins, 88
19. 1986 Montreal Canadiens, 87
20. 1944 Montreal Canadiens, 83
21. 1939 Boston Bruins, 74
22. 1953 Montreal Canadiens, 75
23. 1995 New Jersey Devils, 52
24. 1940 New York Rangers, 64
Western Conference
1. 1984 Edmonton Oilers, 119
2. 2001 Colorado Avalanche, 118
3. 1989 Calgary Flames, 117
4. 2002 Detroit Red Wings, 116
5. 2008 Detroit Red Wings, 115
6. 1999 Dallas Stars, 114
7. 2010 Chicago Blackhawks, 112
8. 2007 Anaheim Ducks, 110
9. 1996 Colorado Avalanche, 104
10. 1998 Detroit Red Wings, 103
11. 1952 Detroit Red Wings, 100
12. 2014 Los Angeles Kings, 100
13. 2019 St. Louis Blues 99
14. 1951 Toronto Maple Leafs, 95
15. 1997 Detroit Red Wings, 94
16. 1990 Edmonton Oilers, 90
17. 1962 Toronto Maple Leafs, 85
18. 1948 Toronto Maple Leafs, 77
19. 1961 Chicago Blackhawks, 75
20. 1967 Toronto Maple Leafs, 75
21. 1943 Detroit Red Wings, 61
22. 1947 Toronto Maple Leafs, 72
23. 1942 Toronto Maple Leafs, 57
24. 1949 Toronto Maple Leafs, 57
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Here we go:
Eastern Conference, 1st Round
9. 2003 New Jersey Devils vs. 24. 1940 New York Rangers. I tweaked the seedings so I didn't end up with Devils vs. Devils in the 1st Round. This Ranger team was very solid, but not nearly deep enough to stand up to the best Devils team ever. Devils in 5.
11. 2018 Washington Capitals vs. 22. 1953 Montreal Canadiens. Another tweak to avoid a same-team 1st Round matchup. If these were the Habs of 1956 to 1960, I would trust Jacques Plante to handle Alex Ovechkin. But these were the Habs with Gerry McNeil in goal. Caps in 5.
12. 1969 Montreal Canadiens vs. 21. 1939 Boston Bruins. The Kraut Line led by Milt Schmidt, and the late-game heroics of "Sudden Death" Mel Hill give the B's a chance. An older Frank Brimsek in goal might have helped, but the '39 Bruins, with Brimsek as a rookie, had more points than the '41 Cup-winning version. Canadiens in 6.
13. 2011 Boston Bruins vs. 20. 1944 Montreal Canadiens. Brad Marchand is not going to stop Maurice Richard. Nor is Zdeno Chara. Neither is Tim Thomas. Canadiens in 5.
14. 1993 Montreal Canadiens vs. 19. 1986 Montreal Canadiens. This was the only time I couldn't avoid a same-team 1st Round matchup, and it's the last 2 Habs Cup winners. A few of the 1970s holdovers like Larry Robinson and Bob Gainey were still around, but the '93 team was better. '93 Canadiens in 6.
15. 1956 Montreal Canadiens vs. 18. 1991 Pittsburgh Penguins. Jacques Plante facing Mario Lemieux, Jaromir Jagr and Ron Francis without a mask? With Doug Harvey also defending against them, I like the Habs' chances. Canadiens in 5.
16. 2009 Pittsburgh Penguins vs. 17. 1960 Montreal Canadiens. Jacques Plante facing Sidney Crosby and Evgeni Malkin with a mask? And Harvey and Bernie "Boom-Boom" Geoffrion reacting to Sid the Kid doing his little dives? Canadiens in 4 straight.
Western Conference, 1st Round
9. 1996 Colorado Avalanche vs. 24. 1949 Toronto Maple Leafs. Ted "Teeder" Kennedy and company aren't going to be fast enough for Joe Sakic's bunch. Avs in 5.
10. 1998 Detroit Red Wings vs. 23. 1942 Toronto Maple Leafs. Stopping prime Syl Apps? There's an app for that, and it's Viacheslav Fetisov and Nicklas Lidstrom. Wings in 5.
11. 1952 Detroit Red Wings vs. 22. 1947 Toronto Maple Leafs. Tweaked to avoid a Wings vs. Wings matchup in the 1st Round. This was the year the Wings did the 1st 8-game sweep in Playoff history (hence the guy throwing the 8-legged octopus onto the ice, starting the tradition), a feat that ended up being matched only by the '60 Canadiens. The Leafs weren't ready for the Production Line at its peak. Wings in 5.
12. 2014 Los Angeles Kings vs. 21. 1943 Detroit Red Wings. This was when the Howe starring for Detroit was Syd, not Gordie. I guess it depends on whether the referees let the Kings cheat. Or maybe it doesn't. Maybe they're just too deep for any 1940s team. Kings in 7.
13. 2019 St. Louis Blues vs. 20. 1967 Toronto Maple Leafs. Here's a nice matchup: The current Stanley Cup holders against the last of the "Original Six" champs, a pair of veteran, knowledgeable squads. But who do the current Blues have that can stop the Big M, Frank Mahovlich? Leafs in 6.
The 1967 Toronto Maple Leafs
14. 1951 Toronto Maple Leafs vs. 19. 1961 Chicago Blackhawks. Can Turk Broda stop a young Bobby Hull and a young Stan Mikita? Can a young Glenn Hall stop prime Teeder Kennedy? The latter is more likely. Hawks in 5.
15. 1997 Detroit Red Wings vs. 18. 1948 Toronto Maple Leafs. Teams in the Fighting Forties didn't get much deeper than the '48 Leafs, Syl Apps' last team. But they weren't nearly deep enough to take on a team assembled by Jim Devellano and coached by Scotty Bowman. Wings in 4 straight.
16. 1990 Edmonton Oilers vs. 17. 1962 Toronto Maple Leafs. Remember, this Oiler team has prime Mark Messier, Glenn Anderson, Kevin Lowe, and a young Adam Graves; but it doesn't have Wayne Gretzky, Jari Kurri or Paul Coffey; and Bill Ranford has replaced Grant Fuhr as the starting goalie. And when Punch Imlach's Leafs are veteran-laden, they're not old yet. Leafs in 5.
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Eastern Conference, 2nd Round
1. 1977 Montreal Canadiens vs. 20. 1944 Montreal Canadiens. The '44 Habs, with the Punch Line of Maurice Richard, Elmer Lach and Toe Blake, might have been the fastest team anyone had yet seen. But the '77 edition was the ultimate in "The Flying Frenchmen." '77 Canadiens in 5.
2. 1973 Montreal Canadiens vs. 17. 1960 Montreal Canadiens. The '73 Habs collected more points in a season than anyone yet had. But old Henri Richard and the rest couldn't keep up with young Henri, old Maurice, prime Geoffrion, prime Harvey, prime Plante, and prime Jean Beliveau. '60 Canadiens in 6.
The 1960 Montreal Canadiens
3. 1972 Boston Bruins vs. 15. 1956 Montreal Canadiens. In '56, the Habs were burning over their Finals losses to Detroit in '54 and '55, and were hungry. In '72, the Bruins were burning over their Playoff loss to the Habs the year before.
The difference could be that, in '56, the Habs had a bunch of rookies making good, including Henri Richard; while the '72 Bruins were an outfit of prime stars, already battle-tested. Not that the '56 Habs didn't have Maurice Richard, Butch Bouchard and Harvey. But this was the best Bruin team ever. Bruins in 6.
4. 1982 New York Islanders vs. 14. 1993 Montreal Canadiens. The '93 Habs won some time games, including in overtime, including against the '93 Isles, who put together a fun ride. But the '82 Isles were much better. Isles in 5.
5. 1975 Philadelphia Flyers vs. 12. 1969 Montreal Canadiens. In spite of being defending Champions, and then Champions again, the Habs were kind of in a transition from the Beliveau and Henri Richard team of the Sixties and the Yvan Cournoyer, Serge Savard, Ken Dryden and Guy Lafleur team of the Seventies: Cournoyer and Savard were already there, but Dryden and Lafleur weren't.
In '76, they were ready to take the Flyers down and cut their dynasty short. In '69, they wouldn't have been. Flyers in 6.
6. 1994 New York Rangers vs. 11. 2018 Washington Capitals. For all the hype over them, it's easy to forget that the '94 Rangers were among the least deserving Stanley Cup Champions ever. Not just because they were big-money assembled. Not just because half the team was Edmonton Oiler retreads. And not just because Messier is an asshole.
But because they came damn close to both losing the Conference Finals -- both in Game 6 and at home in Game 7 -- and blowing a 3-games-to-1 lead in the Stanley Cup Finals, losing Game 5 at Madison Square Garden and Game 6 in Vancouver before finally holding the Vancouver Canucks off in Game 7 at home.
Mike Richter stopped Pavel Bure on the most famous penalty shot in hockey history. He could stop Ovechkin. And maybe, as a team, the '94 Rangers had more talent than the '18 Caps. But the Caps would not be intimidated by the Rangers. Caps in 7 -- winning at The Garden.
7. 2006 Carolina Hurricanes vs. 10. 2004 Tampa Bay Lightning. Both of these teams should have lost the Finals to a team from Alberta, the former to the Oilers, the latter to the Calgary Flames. Both got robbed by the referees and their boss Gary Bettman. The Bolts needed more help to win. 'Canes in 7.
8. 2017 Pittsburgh Penguins vs. 9. 2003 New Jersey Devils. Sidney Crosby, meet Scott Stevens. If you survive that, meet prime Martin Brodeur. Devils in 7.
Western Conference, 2nd Round
1. 1984 Edmonton Oilers vs. 20. 1967 Toronto Maple Leafs. In 1984, the Oilers dethroned the 1980s Islander dynasty. Now, they face the end of the 1960 Maple Leaf dynasty. Can Tim Horton (then very early in the donut business), Allan Stanley, and the goaltending tandem of Johnny Bower and Terry Sawchuk hold off Gretzky, Kurri, Messier and Anderson? I doubt it. Oilers in 6.
2. 2001 Colorado Avalanche vs. 19. 1961 Chicago Blackhawks. If there were a "Mount Rushmore" of 4 guys who popularized hockey in America, it would be Gordie Howe, Bobby Orr, Wayne Gretzky and Bobby Hull. But, given that I've made all teams full-strength, and thus Peter Forsberg gets added to a very strong and deep Colorado team, I don't think the Golden Jet can do enough here. Avs in 6.
4. 2002 Detroit Red Wings vs. 15. 1997 Detroit Red Wings. The '97 Wings broke a 42-year drought, and are the most beloved team in franchise history. But the '02 Wings, including many of the same players, are the best. '02 Wings in 6.
5. 2008 Detroit Red Wings vs. 12. 2014 Los Angeles Kings. Jonathan Quick is not ready for this Motor City madness. Wings in 4.
6. 1999 Dallas Stars vs. 11. 1952 Detroit Red Wings. Go ahead, Derian Hatcher: Mess with a team that has Gordie Howe on it. I dare you. Wings in 4.
7. 2010 Chicago Blackhawks vs. 10. 1998 Detroit Red Wings. Arch-rivals. There could be some fights. If it were the '13 or '15 Hawks, they might win. But it was the '10 Hawks who had the better record. Experience wins out here. Wings in 6.
8. 2007 Anaheim Ducks vs. 9. 1996 Colorado Avalanche. Patrick Roy. "Roy" is a variation on "Roi," which is French for "King." I don't care how many Niedermayer brothers are on the Ducks. Avs in 5.
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Eastern Conference Quarterfinals
1. 1977 Montreal Canadiens vs. 17. 1960 Montreal Canadiens. Too soon. This should have been the ultimate Finals: The 4-time champs vs. the 5-time champs. The '60 Habs had maybe the best top 10 in NHL history. But the '77 Habs may have had the best top-to-bottom team. '77 Canadiens in 7 -- maybe in overtime.
3. 1972 Boston Bruins vs. 11. 2018 Washington Capitals. How's this for a matchup: Bobby Orr vs. Alexander Ovechkin! But it's also Phil Esposito vs. Braden Holtby. Bruins in 5.
5. 1975 Philadelphia Flyers vs. 7. 2006 Carolina Hurricanes. Let's see how these pampered 21st Century players handle the Broad Street Bullies. Flyers in 4 straight.
1. 1984 Edmonton Oilers vs. 17. 1962 Toronto Maple Leafs. These Oilers have already taken down one part of the Sixties Leafs dynasty in this tournament. No reason why they can't take down another. Oilers in 5.
Still, the '52 Wings could boast a Hall-of-Famer at every starting position: Sawchuk in goal, a defensive pairing of Red Kelly and Marcel Pronovost, and the Production Line of Gordie Howe, Sid Abel and Ted Lindsay. Do the '01 Avs, with Roy, a healthy Forsberg, and the way led by Sakic and the retiring Ray Bourque, have enough depth to get past that? Maybe, but I don't think so. Wings in 7.
4. 2002 Detroit Red Wings vs. 10. 1998 Detroit Red Wings. Yet again, the '02 Wings take on one of their recent forebears. Yet again, they just have too much talent. '02 Wings in 6.
5. 2008 Detroit Red Wings vs. 9. 1996 Colorado Avalanche. This was Lidstrom's team, with Steve Yzerman having retired. I think they may be missing a little something here. Avs in 7.
*
Eastern Conference Semifinals
1. 1977 Montreal Canadiens vs. 5. 1975 Philadelphia Flyers. We already know how this will turn out, since, more or less, it happened, in between, in 1976. Maybe it won't be a sweep this time, but beautiful hockey wins out over winning ugly. Canadiens in 5.
3. 1972 Boston Bruins vs. 4. 1982 New York Islanders. With Clark Gillies, John Tonelli, and even goalie Billy Smith, the early Eighties Isles could fight. Of course, so could the Big Bad Bruins of the Seventies. So the question is: Do the Bruins of Orr, Esposito, Johnny Bucyk and Gerry Cheevers have the talent to overcome the Isles of Smith, Denis Potvin, Mike Bossy and Bryan Trottier? I don't think so. Isles in 7.
Western Conference Semifinals
1. 1984 Edmonton Oilers vs. 11. 1952 Detroit Red Wings. This won't settle the "greatest player ever debate" between Howe and Gretzky. But it will put the Oilers against a tougher team than anybody they'd yet faced. (And let's face it: While they would beat the Flyers in the Cup Finals in '85 and '87, those were not the Flyers of '74 and '75.)
Having the speed advantage won't help the Oilers, because they might not actually have it here. Having Sawchuk rather than Fuhr might help the Wings. Wings in 7.
*
Eastern Conference Finals: 1. 1977 Montreal Canadiens vs. 4. 1982 New York Islanders. Here's how good the early Eighties Isles were: They had the speed and quick-strike capability of the late Seventies Habs, the early Seventies Bruins and the Eighties Oilers; and the toughness of the mid-Seventies Flyers, the early Seventies Bruins and the Eighties Oilers.
The 1982 New York Islanders
But that won't be enough here. Ken Dryden is in goal. Serge Savard, Larry Robinson and Guy Lapointe are on defense. The attack features Guy Lafleur, Yvan Cournoyer, Jacques Lemaire, Steve Shutt and Bob Gainey. That's 9 Hall-of-Famers. And that doesn't count these guys, who aren't in the Hall but were still pretty good: Peter Mahvolich, Doug Risebrough, Doug Jarvis, Yvon Lambert and Rejean Houle.
Take a look at the team photo. See the trophies? From left to right: The Art Ross trophy for most points by a player, Lafleur; the Hart Memorial Trophy, for the Most Valuable Player of the regular season, also Lafleur; the Prince of Wales Trophy, for Eastern Division Champion (now for the Eastern Conference Champions); the Stanley Cup; the Vezina Trophy, for best goaltender, Dryden; the James Norris Trophy, for best defenseman, Robinson; and the Conn Smythe Trophy, for MVP of the entire Playoffs, Lafleur again.
Throw in the Ross, and only Orr in '70, Lafleur in '77 and Gretzky in '85 have ever done it. Orr, as you might guess, also won the Norris in '70, and he scored the Cup-clinching goal, giving him perhaps the greatest individual season in NHL history. Lafleur with Robinson, and Gretzky with Coffey, had their teammates win the Norris in their respective seasons.
Throw in the Vezina, though, and the '70 Bruins didn't turn the trick, as Tony Esposito of Chicago won it. (In fact, no Bruin won it between Frank Brimsek in 1942 and Pete Peeters in 1983.) Nor did the '85 Oilers: Grant Fuhr won it in '88, but in '85, it went to Pelle Lindbergh of the Flyers. But with the '77 Habs, Dryden got it.
Oh yeah: Scotty Bowman won the Jack Adams Award for coach of the year, a trophy not pictured here. The only major award available to the '77 Habs that they didn't win was the Calder Memorial Trophy, for Rookie of the Year, which went to Willi Plett of the Atlanta Flames.
The winningest coach ever, with 9 Hall-of-Fame players, between them winning 7 major trophies. The Habs were just too strong. Canadiens in 7.
Western Conference Finals: 4. 2002 Detroit Red Wings vs. 11. 1952 Detroit Red Wings. No way does one Detroit team roll over so that the other will be stronger and fitter for the overall Finals. The old Wings had a great starting lineup. So did the more recent wings, and they had a strong bench, too. So it's a question of whether the old guys' pride will be enough. It won't. '02 Wings in 7.
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All-Time Stanley Cup Finals: East 1. 1977 Montreal Canadiens vs. West 2. 2002 Detroit Red Wings. A team coached by 43-year-old Scotty Bowman, taking his 3rd Cup, vs. a team coached by 69-year-old Scotty Bowman, taking his record 9th and last Cup.
I've named the '77 Habs stars. Here's what the '02 Wings come with: Steve Yzerman, Brett Hull, Igor Larionov, Brendan Shanahan, Luc Robitaille, Chris Chelios, Dominik Hasek. All past their prime, but all still showing why they're in the Hall of Fame. Nicklas Lidstrom and Sergei Fedorov. Still very much in their prime, and in the Hall. Pavel Datsyuk, not in the Hall yet, but still in his prime then. Kris Draper, Darren McCarty, Kirk Maltby and Tomas Holmstrom, good holdovers from the 1997 and '98 Champs.
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The 2002 Detroit Red Wings
Would Bowman being older and wiser in 2002 make the difference? Probably not: As I said in my NFL piece, everybody involved has been fully briefed on what has happened since. Any knowledge available to '02 Bowman is also available to '77 Bowman. The old man may have a better idea of how to use it, but the middle-aged man can still use it.
The difference may well be in the goalies. In the regular season, Hasek was as good as anyone, ever. But in the postseason, especially the further he got, the shakier he got. Dryden got better the further he got. Canadiens in 7.
The 1977 Montreal Canadiens: All-Time Stanley Cup Champions.
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