Debating the biggest ‘What if?’ in Stanley Cup playoff history
The Colorado Avalanche looked unstoppable…until they didn’t. The 2025-26 Presidents’ Trophy winners breezed through Rounds 1 and 2 of the playoffs, but injuries to their superstars hindered them in a shocking sweep defeat to the Vegas Golden Knights. Now, the Avs are just another playoff “What if?” story, a team that seemed poised to go all the way only to get unceremoniously bounced from the postseason early.
But they are just one of many teams who suffered spring heartbreak of that magnitude. So, Roundtable: What is the biggest Stanley Cup playoff “What if?” of all-time? It can be a bad bounce, a shocking upset, a hot goalie, a controversial call…the only criterion is that it must have happened during, or directly impacted, the playoffs.
MATT LARKIN: So many choices. Brett Hull’s skate comes to mind, as does Steve Smith’s own goal. But I must admit my first thought was Kerry Fraser’s missed high stick call on Wayne Gretzky in 1993. Unlike the Buffalo Sabres in 1999, the Toronto Maple Leafs were leading their series, up 3-2 on the Los Angeles Kings in the Western Conference Final, a goal away from Toronto’s first Stanley Cup Final since 1967. No only did Fraser miss what should’ve been (based on the rulebook at the time) a five-minute major on Gretzky for high-sticking, but Gretzky himself directly benefited, scoring the overtime winner while Gilmour was off the ice getting stitched up, forcing a Game 7, which L.A. won. We’ll never know if Toronto might’ve handled the Montreal Canadiens in the Cup Final, but the Leafs were an extremely balanced and star-studded squad. They were robbed of their best shot to end the drought.
PAUL PIDUTTI: My first thought went to Dominik Hasek’s injury at the 2006 Turin Olympics. The 2005-06 Ottawa Senators were a dominant force. First in goals. Second fewest allowed. Top seed in the Eastern Conference. The ‘Pizza Line’ of Daniel Alfredsson (103 points), Dany Heatley (50 goals), and Jason Spezza (90 points in 68 games) were at the peak of their powers. Zdeno Chara and Wade Redden finished fourth and fifth, respectively, in Norris voting. Bryan Murray’s crew was young, fast, and tough, perfectly built for the post-lockout NHL. And 41-year-old Hasek was second in the NHL in save percentage (.925) and cruising… until a brutal groin injury in Italy ended his season. The Sens lost the second round in five games to Buffalo despite outshooting the Sabres by an average of 10.2 shots per game. Ray Emery (.864 save percentage in series) went leaky and the Sens were cooked. With Hasek in net, would the Sens have won the Cup? Might a deeper run have been what the core needed to get past the Anaheim Ducks in the 2007 Final? Would a different result have shifted the course of the franchise from pesky (but Cup-less) Sens to the cap era’s first mini-dynasty? Might Ottawa have a new arena today? What if…
ANTHONY TRUDEAU: Six words:“Too many men on the ice.” The Boston Bruins were leading late in Game 7 of their 1979 NHL Semifinal matchup with their mortal enemies, the dynastic late ‘70s Montreal Canadiens, who had beaten them in the previous two Stanley Cup Finals. Boston’s Don Marcotte went over the boards to take his usual spot shadowing Habs’ superstar Guy Lafleur. The problem? With Lafleur double-shifting amid a desperate Montreal push, five other Bruins had already taken the ice for their usual matchups. Lafleur buried Jacques Lemaire’s drop pass to tie the contest at 4-4 just over a minute later, and Yvonne Lambert would later jam home an overtime winner for the Canadiens. So many dominoes might have fallen differently without the Bruins’ deployment blunder. Would Ken Dryden still have retired on a losing note? Would the loss of their four-peat relegate those legendary Canadiens beneath the subsequent Islanders and Oilers dynasties in the annals of NHL history? Would Brad Park finally have gotten his championship moment if the Bruins had advanced? And if Don Cherry doesn’t get the axe for the blunder, do his coaching credentials end up outweighing his subsequent career as a media firebrand? There are enough alternate history scenarios stemming from that one penalty to make the X-Men blush.
SCOTT MAXWELL: When you think of the best players to never win a Stanley Cup, Jarome Iginla is likely one of the first names that comes to mind. Despite a long and storied career in the league, he only came close to winning a Cup once in 2004. That year’s Cup Final also had a controversial decision determine the series: the infamous Martin Gelinas no-goal in Game 6. Whether you think the puck had crossed the line or not, it played a pivotal role in the series and gave the Tampa Bay Lightning the juice they needed to win that game and beat the Calgary Flames in seven. If the goal counts, how does Iginla’s career play out differently now having the Cup in his trophy case? Heck, do the Lightning still find a way to tie that game anyways, and does the series plays out the same? Regardless, having one decision leave one of the game’s best players without a Cup is certainly one of the sport’s biggest ‘What Ifs.’
And don’t get me started on the 2014 free agency, when Iginla chose the regressing Colorado Avalanche over the rising Lightning. He possibly could have been the piece that put them over the edge in the 2015 Cup Final against the Chicago Blackhawks. Iginla’s entire career is littered with ‘What Ifs’ that could have resulted in Stanley Cup wins.
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