Stanley Cup Playoffs Pressure Rankings: Which team needs to win the most

The answers at the top are obvious.

The 2025 Stanley Cup Playoffs begin on Saturday, and this is where the pressure really kicks up a notch for everybody involved. For better or worse, fair or not, this is where reputations and legacies get made, and some teams are going into the playoffs with significantly higher expectations — and pressure — than others.

That is especially true for teams that have consistently fallen short in recent years, have not had playoff success with their current team, or are years removed from their most recent championship.

Every year those teams do not win, the outside noise gets a little louder.

So let’s take a look at all 16 teams in this year’s field and rank them based on which are facing the most pressure and highest expectations to win. Not even necessarily the Stanley Cup itself. But just the expectation for some kind of a deep playoff run with some sort of success.

1. Toronto Maple Leafs. This is the obvious and easy answer. It is the lowest-hanging fruit imaginable. This fruit is hanging so low it is practically on the ground. When it comes to expectation and pressure to win in the playoffs, there is not a team in the league that comes close to this Maple Leafs group.

In their eight previous postseasons with this core dating back to 2016-17, they have lost in the first-round seven times.

They have won just a single playoff series, and only one game beyond the first round.

They have lost as favorites, as underdogs, to rivals, they have blown leads, they lost on home ice, they have lost on the road and pretty much every way imaginable.

Defense and goaltending are always the focal point, but a lot of their recent playoff defeats have been the result of a lack of goal-scoring. Sometimes from their core players. Sometimes from their depth. Sometimes from both.

Every year we keep saying, “if they do not win this season, they might have to make some changes to their core.”

Then it never happens.

They may not have a choice this season as Mitch Marner and John Tavares are both pending unrestricted free agents. This feels like this group’s last shot at it as currently constructed. They have repeatedly failed. Will any of that change? And if it does not, how much will the roster change?

2. Edmonton Oilers. The pressure here comes from the fact they have two of the best players in the world — Connor McDavid and Leon Draisaitl — and only have two deep playoff runs to show for it in nearly a decade. They made it to Game 7 of the Stanley Cup Final a year ago, nearly pulling off an improbable 3-0 series comeback, but ended up falling just short.

Every year they have prime-era McDavid and Draisaitl on their roster there should be a championship level of expectation, and an all-in mentality from the organization.

Every year they fail to win seems like a missed opportunity.

The frustrating part for the Oilers this season is the harsh reality that this team probably is not going to win. Depth is still a concern, the defense is going to be dealing with a huge loss early on without Mattias Ekholm (half of its only good pairing) and nobody should trust Stuart Skinner in goal.

Going another year into McDavid and Draisaitl’s career without a championship is just going to keep building the pressure in future seasons.

3. Carolina Hurricanes. Every year the Hurricanes go into the playoffs as a favorite. They are consistently one of the best teams in the league, a relentless defensive team, always dominating the underlying numbers and possession metrics, and always looking like a team that has very few weaknesses.

But they always keep falling just short of the Stanley Cup Final. When you keep winning in the regular season and keep getting close in the playoffs without actually breaking through, the pressure definitely starts to build. I feel like it is even higher this season following their role of the dice on Mikko Rantanen.

Trading for him seemed like an all-in move to give them the elite, superstar level scorer they have needed.

It was a gamble given his contract status as a pending unrestricted free agent, but it was the type of bold gamble that might get a team over the hump.

But when they were unable to get him re-signed to a long-term contract extension they traded him again to the Dallas Stars.

The end result from where they started the season is a net-win in terms of long-term assets (they essentially traded Martin Necas and Jack Drury for Logan Stankoven, Taylor Hall and two first-round draft picks). If you can remove the month where they had the Rantanen storyline hanging over everything it is really hard to be mad at that.

But you can not remove the Rantanen storyline. It happened. They had him, and the hope of what he could provide even if on a short-term, rental basis.

Does any of this get them closer to a Stanley Cup this season? Will fans be left wondering what might have happened had they made one serious run with Rantanen and let the free agency result be what it was? Those are big questions that will come up if they do not win.