Siegel outlines Toronto’s lineup needs clearly. The team needs a legitimate option at the third-line center position and a right-handed shooting top-four defenseman. The Maple Leafs already have right-handed shot defensemen such as Chris Tanev, Jani Hakanpää (injured), Conor Timmins, and Philippe Myers. Still, Tanev is arguably the only one of the quartet that should command top-four minutes.

Siegel argues that Toronto should target a defenseman like Colton Parayko rather than short-term options like Luke Schenn or David Savard. An acquisition of Parayko would have plenty of challenges to overcome largely due to the full no-trade clause in his contract. Still, given that he’s averaging over 24 minutes a night with the St. Louis Blues, has already scored 12 goals in 55 games, and is known for his shot-blocking and physicality, Parayko is an ideal trade candidate for the Maple Leafs.

Ryan O’Reilly of the Nashville Predators was the only player mentioned as a potential candidate to take over third-line duties. He’s on a remarkably affordable $4.5MM salary through the 2026-27 season without trade protection and already has familiarity with the Maple Leafs organization. Whether it’s O’Reilly or another center, Toronto must improve upon Pontus Holmberg, who went scoreless in the Maple Leafs’ opening-round loss against the Boston Bruins in last year’s playoffs, as their third-line center.

As much as a big splash may satisfy Toronto’s needs, a lot rests on how much they’re willing to part with at the deadline. In the last five years alone the Maple Leafs have traded a first-round pick to offload the contract of Patrick Marleau, Trevor Moore in a package for Jack Campbell, Mason Marchment for Denis Malgin, a first-round pick for Stefan Noesen, a first-round pick to offload the contract of Petr Mrázek, a first-round pick for O’Reilly, and another first-round pick for Jake McCabe.

Some of those trades worked out better than others but Toronto has only managed to move beyond the first round of the Stanley Cup playoffs once over that stretch. All those moves were made during the last administration guided by Kyle Dubas, and current general manager Brad Treliving took a different approach last year. The highest-valued asset that Treliving moved at last year’s deadline was the New York Islanders’ 2024 third-round pick in a package for defenseman Joel Edmundson.

Siegel points out that the only way the Maple Leafs will manage to make any splashes is if they’re willing to move prospects such as Fraser Minten, Easton Cowan, or Ben Danford, and their 2026 first-round pick. Toronto has not indicated an eagerness to include any of the previously mentioned assets but it’s difficult to disagree with Siegel’s thinking.