Can a team built with four players making so much of the salary cap win a Stanley Cup, or will a salary cap hole swallow up their shot at greater success?

The Edmonton Oilers face a critical season ahead as they look to capitalize on their current roster while managing the implications of a salary cap largely dominated by their top players. If they don't win the Stanley Cup in 2024-25, they may struggle to do so at all. 

Last season, Connor McDavid, Leon Draisaitl, Evan Bouchard, and Zach Hyman elevated their game, nearly leading the team to a Stanley Cup victory, falling one win short in a tight 2-1 Game 7 loss against the Florida Panthers. However, the looming question remains: can a team with a significant portion of its salary cap allocated to just a few players achieve ultimate success?

With discussions surrounding an eight-year, $13.5 million extension for Draisaitl and a potential $15-16 million deal for McDavid in 2025, the Oilers must navigate the complexities of a roster that could soon be heavily weighted toward its elite players. 

Early projections suggest that in 2026, the quartet of McDavid, Draisaitl, Nurse, and Bouchard is likely to consume about 48 percent of a roughly $100-million salary cap. Currently, that same quartet of top four players accounts for approximately 38 percent of the team's total salaries. This raises questions about the sustainability of such a financial model, especially given the Toronto Maple Leafs' struggles with a similarly high payroll.

The Maple Leafs have been criticized for their inability to advance beyond the first round of the playoffs, largely due to the financial burden of their core four — Auston Matthews, Mitch Marner, William Nylander, and John Tavares — who consume over 53 percent of their cap space. This experience serves as a cautionary tale for the Oilers. While McDavid and Draisaitl are among the most talented players in the league, history suggests that a top-heavy roster can be problematic when it comes to building a balanced team capable of deep playoff runs.

Fans are sure to debate the comparisons between the Leafs' core and the Oilers' core, but that's an argument for another day. The fact is that investing too much in too few players is an issue. 

For the Oilers, the next season is critical. They must make the most of their current salary cap situation, where their star players' contracts are still manageable. Value deals for Ryan Nugent-Hopkins ($5.125 million), Hyman ($5.5 million), Mattias Ekholm ($6 million), and Stuart Skinner ($2.6 million) provide some flexibility. However, once McDavid and Draisaitl secure their lucrative extensions, the team could struggle to retain depth players and address other positional needs.

Ultimately, the Oilers have a narrow window to prove that a roster heavy with star power can indeed contend for a championship. The debate about whether a team can win the Stanley Cup with four players making the bulk of the salary cap will be tested in the coming seasons. This isn't to suggest winning a Cup is impossible with your best players making most of the team's money, but it's a lot more difficult when a franchise is paying full value for that talent. 

The only alternative is to either convince these stars to take team-friendly deals or trade someone.