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The Toronto Maple Leafs have a talented roster, but with the salary cap constraints in the NHL, they must make some difficult decisions to remain competitive. To achieve long-term success, the Maple Leafs should consider shedding certain contracts that either don’t align with their needs or hinder their flexibility. Here are a few contracts the team should seriously consider moving or buying out at all costs.

1. Matt Murray (Goalie)

Contract Overview: Matt Murray signed a two-year, $6.25 million deal in the summer of 2022, coming off a Stanley Cup win with Pittsburgh and a successful tenure in Ottawa. However, his tenure with the Leafs has been filled with inconsistency and injury concerns.

Why It Should Be Shed: The injury-plagued nature of Murray’s career has continued to haunt him in Toronto. He has struggled to find stability between the pipes, and his play hasn’t lived up to the financial commitment the team made. With other capable options, such as Ilya Samsonov, who is proving to be more reliable, Murray’s contract becomes a liability. Moving his contract would free up cap space for better investments in depth players or future talent.

How To Shed It: The most straightforward approach is for the Leafs to find a trade partner willing to take on his contract. If no suitors are found, buying out Murray could be an option, though the buyout penalties would stretch across multiple seasons. Regardless, the team would benefit from moving on.

2. John Tavares (Center)

Contract Overview: Tavares is locked into an $11 million annual salary that runs through 2025. While he remains a highly skilled player and the Leafs’ captain, his contract is one of the highest on the team.

Why It Should Be Shed: Although Tavares is still a point-per-game player, his contract is one of the highest in the league for a player who is no longer in his prime. The salary cap is a precious resource, and with Toronto already carrying substantial deals for Auston Matthews, Mitch Marner, and William Nylander, Tavares’ contract becomes harder to justify. In addition, he’s not as effective in the postseason as other stars on the roster, making his cap hit even more cumbersome when the Leafs need every penny of cap space to build a deeper, more balanced roster for the playoffs.

How To Shed It: This would be a very difficult decision, given Tavares’ leadership and legacy with the Leafs, but the team could potentially find a trade partner, though it would likely require salary retention. If not, the team may look to buy out his deal, but this comes with heavy long-term cap implications, which could make it a last resort.

3. Justin Holl (Defenseman)

Contract Overview: Holl is in the final year of a contract that pays him $2 million annually. While not an egregious cap hit, Holl has been a polarizing player for the Leafs, often underperforming compared to the expectations that come with his role as a top-six defenseman.

Why It Should Be Shed: Holl’s defensive play has been inconsistent, and with the Leafs’ defensive core needing stability, moving him would be a smart move. Toronto needs to upgrade its blue line if it wants to contend for a Stanley Cup, and Holl doesn’t provide the level of play the team needs for that. His lack of physicality and inability to shut down top forwards makes him expendable, especially with the potential of younger players like Rasmus Sandin or Timothy Liljegren stepping into larger roles.

How To Shed It: The Leafs can likely find a trade partner for Holl, as he’s a serviceable, affordable depth defenseman. If no trade options emerge, the team could look at waivers or consider a buyout, though this may not free up much cap space.

4. Alexander Kerfoot (Forward)

Contract Overview: Kerfoot signed a four-year, $14 million deal in 2021. At $3.5 million per season, his deal is one of the more manageable on this list, but his production has not lived up to the expectations.

Why It Should Be Shed: Kerfoot has shown flashes of skill but has never quite reached the level expected for a player making $3.5 million. His scoring is inconsistent, and with the Leafs’ abundance of talented forwards, Kerfoot’s role has been limited. The Leafs could use the cap space for a more reliable, consistent option, especially if a trade opportunity arises for a better fit.

How To Shed It: The Leafs should explore trade options for Kerfoot, as there could be suitors for a skilled, versatile forward with some term remaining on his deal. If a trade isn’t possible, Toronto could consider putting him on waivers or using a buyout, though it would be preferable to avoid the long-term penalty.

5. Wayne Simmonds (Forward)

Contract Overview: Wayne Simmonds, at this point in his career, is largely a depth player, earning $900,000 on a one-year contract.

Why It Should Be Shed: Simmonds is a fan favorite for his leadership and toughness, but he is no longer the player he once was. His production has dropped significantly, and while his physicality may still be an asset in certain situations, the Leafs need to get younger and faster to remain competitive. A roster spot for a player like Simmonds could be better used for a more dynamic forward or someone who can contribute more regularly.

How To Shed It: Since Simmonds is on a one-year deal, it is likely that the team will simply not re-sign him for next season. If they are looking to make changes mid-season, though, moving him to a contender looking for depth could be a possibility.

Conclusion

The Maple Leafs have an enviable amount of talent, but they also have several high-priced contracts that could limit their future success. Shedding the contracts of players like Matt Murray, John Tavares, Justin Holl, Alexander Kerfoot, and Wayne Simmonds could open up cap space for better investments and allow the team to build a more well-rounded roster. Although some of these moves would be difficult or controversial, they may ultimately be necessary for Toronto to contend for a Stanley Cup in the near future.