Sports are so generous. Not only do we get the plays and games that make our blood rush and our stomachs churn, we also get to ponder how legacies and legends would be affected if a bounce, coach’s decision or a referee’s call had gone the other way. That’s how the “What If?” game works.
For the next little while, Sportsnet.ca is going to run an ongoing “What If?” feature, crafting alternative histories stemming from events big and small. This week, we wondered “What if some of the best players and teams in hockey history had not had the misfortune of bumping up against all-time dynasties?”
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The way it went
While the Chicago Blackhawks and Pittsburgh Penguins can rightly take umbrage at the idea we’re living in a post-dynasties NHL, there’s no denying things are a lot more egalitarian than they used to be.
Consider, for a moment, that between the springs of 1976 and 1988, three teams — the Montreal Canadiens, New York Islanders and Edmonton Oilers — won all 13 Stanley Cups handed out. With signature games from that era and others all over our Sportsnet channels right now, I started thinking about the teams that butted up against greatness and never broke through.
For every squad that ultimately grabs the torch from the previous standard-bearer — a la the Oilers usurping the Islanders in the mid-80s — there are others that fade into history with no glowing rings to keep their legacy illuminated.
What’s lost in the shuffle
Even the greatest outfits in hockey history win games and titles by the skin of their teeth. The Islanders’ dynasty began on an overtime goal in Game 6 of the 1980 final that was offside by no small margin. The Oilers won Cup final series that featured Game 7s and crazy triple-overtime contests that could have gone either way. Every time a revered champion grabs or defends the belt, it seems like an inevitable outcome — but that’s just hindsight working it’s hazy magic.
Possible hockey history re-writes
• We’re going to focus on three teams; the Ray Bourque Boston Bruins, the ‘French Connection’ Buffalo Sabres and the second generation Philadelphia Flyers. Let’s start with Bourque and the B’s.
When, inevitably, somebody makes a documentary about the 20-year Boston sports run that began with the New England Patriots upsetting the St. Louis Rams at the Super Bowl in February, 2002, the opening scene-setter should be footage of the parade that city threw Bourque about eight months prior for winning a Cup as a member of the Colorado Avalanche. That’s how desperate ‘Beantown’ was to celebrate winning something before it started winning everything.
Though Bourque got his happy ending, the Avalanche chapter of his career surely never happens if the Bruins teams he played on a decade earlier broke through. In addition to having an all-world defenceman, those squads also featured the signature power forward of the day, Cam Neely. Boston advanced to the 1988 and ’90 Cup final, facing Edmonton both times. I remember asking Bourque about those clubs during the leadup to the 2016 Winter Classic held at Gillette Stadium, home of the Patriots. Though acknowledging the B’s were in over their head in ’88, he really felt the squad had what it took to beat an Edmonton side that no longer featured Wayne Gretzky in 1990. “I thought we matched up way better,” he said. “I thought we were deeper. I thought we had enough to get it done.”
Boston dropped Game 1 of that final on home ice in triple-overtime and never really recovered. The next year, they had a 2-0 series lead on Mario Lemieux and the Pittsburgh Penguins in the Eastern (then Wales) Conference final. In Game 3, Ulf Samuelsson laid his infamous hit on Neely and the Penguins ripped off four consecutive wins before downing a Cinderella Minnesota North Stars team in the final. From 1988 to ’92, Bourque and the Bruins lost to the eventual Cup winner on four occasions (Edmonton twice, Pittsburgh twice) and a finalist once (Montreal in 1989).
Of course, had Bourque won in Boston, we never would have got Bob Cole’s famous, “You’ve got your Cup, Ray!” call in 2001.

• In a seven-season stretch from 1974-75 through 1980-81, the Buffalo Sabres posted a .646 points percentage. The only teams with a higher mark during that time were a dynamite Flyers club (.675) and a Montreal squad regarded by many to be the best in league history (.738).
Buffalo, led by the line of Gilbert Perreault between René Robert and Rick Martin, lost the first all-expansion final to the Flyers in six games in 1975. It also lost playoff series to Islanders teams that eventually won four straight Cups on three occasions (1976, ’77 and ’80). What if Buffalo had been able to win that Cup final versus Philly or had come along during some era other than the one where Montreal ripped off four straight championships before the Islanders did the same? Western New Yorkers — who’ve never celebrated a Stanley Cup for the Sabres or a Super Bowl for the hard-luck Buffalo Bills — would have at least have one parade to re-live over and over again.
Perreault played his entire 17-year career with Buffalo and registered 1.14 points-per-game in 90 post-season contests, good for the sixth-best total all-time among players with at least 75 career playoff games.
The only skaters with better marks — Gretzky, Lemieux, Mike Bossy and Jari Kurri — all won at least two championships.
• A decade after the ‘Broad Street Bullies’ punched their way into hockey lore with back-to-back titles in 1974 and ’75, the Flyers were back in the final led by rookie coach Mike Keenan, Norris-calibre defenceman Mark Howe and a new generation of forwards featuring Tim Kerr, Brian Propp and Dave Poulin. In the four seasons Keenan guided the Flyers from 1984-85 through 1987-88, the team posted a .637 points percentage. The only squad with a better mark during those years was, of course, the Gretzky-led Oilers (.677).
Like Bourque’s Bruins, Philly was overmatched the first time it met Edmonton in the spring of 1985. But, two years later, the Oilers required seven games to dispatch a banged-up Philly squad.
What if Philly had pulled that decisive contest out? Well, the Flyers wouldn’t be on a five-series losing streak in the Cup final. The Pat Quinn-coached 1980 squad — still powered by guys from the mid-70s Cup years — lost to the Islanders, Keenan lost twice to Edmonton, Eric Lindros was swept by Detroit in 1997 and the 2010 team with Mike Richards and Jeff Carter leading the way was downed by Chicago.
Mark Howe retired without ever getting his hands on the Cup that his dad, Gordie, lifted four times. On the flip side, had Edmonton lost to Philly in 1987, Gretzky’s record in the final would be an even 3-3. (What a bum!) Only six guys — Kurri, Gretzky, Bossy, Mark Messier and Glenn Anderson — scored more playoff goals in the 1980s than Propp, and each of the formers own at least four rings.
Propp — like Poulin, Kerr and the 1987 playoff MVP, Ron Hextall — retired without ever winning a championship.
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