Cap Hell continues to rain down on the Leafs and NHL.

This task was far from easy, as the Maple Leafs' top-heavy roster, with four players accounting for $40 million, coupled with the flat cap, wreaked havoc on the Leafs' management team.

Presently, the team finds itself entangled in two major negotiations involving William Nylander and Auston Matthews. Matthews, being integral to the Maple Leafs' operations, will determine the team's long-term prospects by committing to an extension that facilitates cap management. I believe Matthews will stay and do his part to help the organization work within the cap constraints.

However, the elephant in the room for the Toronto Maple Leafs is what to do with winger William Nylander. Nylander's game has shown consistent improvement over the past three years, particularly in his playoff performances.

When the Maple Leafs faced adversity and their offence stalled, Nylander consistently stood out as a goal-scoring threat and posed a constant challenge to his opponents. He quietly maintains a 75 to 85-point season and displays exceptional poise with the puck.

The team now faces a critical decision. With newly appointed general manager Brad Treliving at the helm, the organization must determine whether they are willing to retain Nylander, who demands an annual salary of around $10 million or trade him to free up cap space and acquire assets to advance the team's interests.

Trading Nylander may be a tough pill to swallow for many Leafs fans who have grown fond of him as a player. However, Nylander might become a casualty of the business side of hockey, as the Maple Leafs must make changes to fit better under the cap. The team also struggles with short-terming and lowballing their bottom six and defence due to financial constraints imposed by the large contracts upfront.

In the past three days, the Maple Leafs have undergone a significant roster overhaul, removing six players and bringing in replacements on one-year deals. Aside Reaves who signed a multi year deal, the additions of Klingberg, Domi, and Bertuzzi have pushed the Maple Leafs over the cap by more than $8 million.

Fortunately, the team can utilize an LTIR position for Jake Muzzin, which frees up over $5 million of cap space, leaving them with around $3.2 million in overage.

Four other NHL teams, including the Tampa Bay Lightning, Canucks, Vegas, and Pittsburgh, also find themselves above the salary cap limit. The flat cap issue has made it increasingly challenging for teams to make deals, leading them to seek financial support from other organizations through salary retention and draft pick exchanges.

NHL general managers are hopeful that this cap conundrum will come to an end after this year. There are indications that the cap will begin to rise again, potentially increasing by almost $4 to $5 million per season. This development is of utmost importance, as the current cost of doing business hinders teams' ability to improve through conventional means.