Pressure is a significant factor in the NHL, manifesting differently across teams. While certain clubs focus on development with hopes of playoff berths, others carry the heavy expectation of winning the Stanley Cup, with time always a looming factor. The Florida Panthers have recently made reaching the Stanley Cup Final seem straightforward, even achieving victory last season with remarkable ease. However, the path to success is not uniform, and for teams yearning to win their first Cup, the ongoing failures prompt tough conversations each offseason. This analysis will delve into several teams facing considerable pressure and the potential need for significant changes to break their playoff droughts.

The Toronto Maple Leafs are now in a position where they must confront their postseason failures. After parting ways with Mitch Marner, who opted not to re-sign with the club, the Leafs face a critical juncture despite retaining Auston Matthews and William Nylander and extending John Tavares and Matthew Knies. However, pressing questions remain regarding the defense, particularly the performance of Morgan Rielly as the team's primary defenseman. Additionally, the health of goaltenders Joseph Woll and Anthony Stolarz will be vital for Toronto's success. General Manager Brad Treliving's recent moves suggest a shift toward a more physical team capable of competing with rivals such as Florida as well as Ottawa and Montreal. Should these efforts fall short again, the upcoming summer may raise doubts regarding the team's long-term strategy.

The New York Rangers, after what many perceived as a partial overhaul last season, have continued their reconfiguration with another wave of changes. Owner James Dolan's expectations for a Stanley Cup are unyielding, and the departures of Chris Kreider and K'Andre Miller raised eyebrows. However, the addition of J.T. Miller and the signing of Vladislav Gavrikov indicate a strategic realignment under new coach Mike Sullivan, who boasts a talented roster including Mika Zibanejad, Artemi Panarin, and Igor Shesterkin. With Panarin set to enter free agency next summer, the stakes are high. Failure to secure the Cup or even make the playoffs could lead to significant organizational shifts for the Blueshirts.

The Los Angeles Kings, having faced the Edmonton Oilers in the playoffs repeatedly over the last four years, were unable to reverse their fortunes last season, prompting a leadership change in the front office. Newly appointed General Manager Ken Holland aims to revitalize the team, particularly given the aging core featuring Anze Kopitar and Drew Doughty. Holland's acquisition of seasoned players like Cody Ceci and Brian Dumoulin aims to fortify the defense. While the Kings possess promising young talent, including Quinton Byfield and Brandt Clark, the expected transition is yet to materialize. Should the aging roster falter or if they again succumb to the Oilers, the organization may need to reconsider its strategy for the future and contemplate reshaping their veteran presence.

The Washington Capitals' approach during free agency last year garnered mixed reactions, with some viewing it as a desperate attempt to support Alex Ovechkin, while others saw it as an opportunity following a successful playoff run. The acquisition of Jakob Chychrun was seen as a strategic move to bolster the defense alongside John Carlson. The Capitals emerged as the top team in the Eastern Conference during the regular season, yet the challenge remains for the franchise to plan for life post-Ovechkin. If they cannot replicate their previous success or secure the Cup, decision-making will need to shift from a hopeful approach to a more discerning strategy.

The Dallas Stars find themselves on the brink of potential major changes this season after parting ways with coach Pete DeBoer following another trip to the Western Conference Final that ended in disappointment. The return of Glen Gulutzan suggests a desire to reinvigorate the squad. However, the situation surrounding elite forward Jason Robertson, who is an impending restricted free agent, poses challenges for Dallas' salary cap management and future planning. With significant commitments already in place for other players, an unsuccessful playoff campaign may necessitate tough choices regarding their roster, particularly concerning Robertson.

The Edmonton Oilers are undeniably in a 'win-now' window, having come agonizingly close to the Cup two seasons ago and facing disappointment in the recent playoffs. The defensive vulnerabilities exposed in their playoff series against Florida serve as a reminder of the difficulties inherent in navigating through a competitive Western Conference. The uncertainty surrounding Connor McDavid's future in Edmonton intensifies the pressure. Should the Oilers fail to secure the Cup and McDavid decline to extend his contract, the organization may find themselves at a crossroads, making extensive changes nearly inevitable.