One of the biggest questions in Penguins history if not THE biggest when it comes to playoff series What If's, is the outcome of the second round playoff defeat to the Washington Capitals in 2018. The defeat would go on to deny the Penguins of the three peat and would allow Washington to storm on to eventually win there first Stanley Cup.
To think the Penguins were only one shot away like a Tom Kuhnhackl post shot from forcing a game seven in a game six where it was fully evident they were out of energy and so hurt is very impressive and itself.
Pittsburgh was simply out of gas and they ran there course
After game two, the signs of fatigue showed for the Penguins as Washington took advantage of both the small and heavy mistakes which costed the Penguins games three and five. Heading into the 2018 playoffs looking to three-peat, the Penguins played 214 combined regular season and Stanley Cup playoff games over the previous two seasons which led them to back to back Stanley cups. Those 214 games clearly got to them and it showed as it was a main factor of losing the series. They simply ran out of the tank that was running on full in 2016 and half tank in 2017 for the previous two seasons.
What if the Penguins win game six in OT and game seven in Washington for back to back to back seasons
With the Penguins sneaking into a third consecutive Eastern Conference Finals and Washington failing once again changes the complete trajectory of the National Hockey League and the Capitals would have more than likely fired Head Coach Barry Trotz and moved on from heavy amounts of core guys like Devante Smith-Pelly, Lars Eller, maybe even one of T.J. Oshie or Jakub Vrana. For the Penguins they would be making more history and moving on to attempt a dynasty.
Pittsburgh would have actually beaten the Tampa Bay Lightning in the ECF
Riding off the moementum of another victorious but sneaky series win over the Capitals, I would in full confidence have the Penguins beating the bolts in six if not seven games in the same fashion the Capitals beat them. Pittsburgh outmatched Tampa and had that veteran experience that would have put them over Tampa Bay, they wouldn't have faced a team like Pittsburgh. Cruising by New Jersey and Boston didn't cement very much since both team's they defeated weren't as deep as them throughout the lineup. Pittsburgh in my opinion with all factors of beating two very good hockey team's would have won a third consecutive Eastern Conference Finals and moved onto the Stanley Cup Finals.
Former Friend is now a foe in Stanley Cup Finals match-up
Facing Marc-André Fleury in the Stanley Cup Finals would have been such long term storytelling and setup the series of the ages in the history of the National Hockey League. The advertising and the timeline would have made the finals and TV ratings skyrocket. The Penguins in my humble opinion would have beaten the Vegas Golden Knights the same way the Capitals did, in dominating fashion and would have cemented the officially label as a dynasty with a three peat as they beat the Golden Knights in five games to win the Stanley Cup. That entire Penguins lineup knew flower very well and would have known how to get him off his game in the Stanley Cup Finals and beat him at his own game. Guys like Derick Brassard, Jamie Oleksiak, and the big guns would have got them to that Stanley Cup. The presence throughout the lineup would have been enough despite how banged up with injuries they were and how tired, they would have got the job done.
What happens now that the Penguins have won once again ?
The entire league would have been grasping to get any player on that Penguins roster especially after winning three straight. The team would have looked radically different and very well Jimmy Rutherford wouldn't have run this team into the ground like he did. The other side of the coin would have been that, the rebuild might have come faster since the Penguins would have lost if they continued to go at it, and they start a quick and early rebuild as Crosby, Malkin and Letang would have four Stanley Cups under their resume's. As of 2025 in the altered timeline, the Penguins would only now be or would have slowly began to creep back into the playoff picture after a rebuild. They had nothing left to prove if they win that third straight cup.
The endless amounts of drama, timeline changes, and stories of a third straight Stanley Cup would have been etched into Hockey history forever for the Pittsburgh Penguins. What If the Penguins were able to achieve this feat. So many questions never can be answered by Penguins fans but we can only say and ask ourselves What If.