After missing the playoffs for the first time in a decade, the Toronto Maple Leafs underwent massive changes in the offseason. John Chayka and franchise legend Mats Sundin were hired to lead a new front office and reshape the organization.
New general manager Chayka and his senior advisor Sundin started their tenure with a stunning win in the NHL Draft Lottery. They rode that momentum and added key pieces, turning over half of the roster. They also hired a new head coach in Jim Hiller.
Noteworthy Leafs' additions included Gavin McKenna with the first overall pick in the NHL Draft, defenseman Darren Raddysh in a sign-and-trade, and decorated free-agent goaltender Sergei Bobrovsky. Chayka and Sundin's high-profile moves come with the minimum expectations of returning to the postseason. Here, in ascending order, are five Maple Leafs feeling the heat heading into the 2026-27 season.
5. Gavin McKenna
There has been much talk about McKenna being insulated by stars like Auston Matthews, William Nylander, and John Tavares as he acclimates to the NHL. The theory is that, unlike previous top picks such as Connor Bedard and Macklin Celebrini, McKenna won't be expected to carry the load.
While there is some truth to that, it is mitigated by the fact that the top prospect is playing in hockey-mad Toronto, which is a whole different animal. If the Leafs hit the quarter mark of the season outside the playoff picture and McKenna has 2 goals and 6 assists, the grumblings of the Toronto fans will start, especially if others from his draft class are performing well.
4. Morgan Rielly
Somewhat miraculously, the Maple Leafs' longest-serving player, defenseman Morgan Rielly, remains on the roster. Early in the offseason, it was a foregone conclusion that he would leave in a trade.
Rielly is still a Leaf because of insufficient trade offers and the Leafs' inability to capably replace his twenty-plus minutes a night. Rest assured, however, if there is not an uptick in his play and he can't be a reliable defender, this year might be his last in Toronto.
3. Darren Raddysh
Raddysh joining his hometown team after a breakout season is potentially a great story. His booming shot gives the Maple Leafs a weapon for the team's power play.
The right-handed defenseman made the most of his opportunity with the Tampa Bay Lightning in 2025-2026. He put up 22 goals and 48 assists in 73 games, making up for Victor Hedman's absence. Chayka signed him to an eight-year deal with an $8.5 AAV. It puts pressure on him to live up to the contract and show his numbers weren't a one-year blip.
2. Sergei Bobrovsky
Chayka, likely at the behest of veteran Leaf players, decided the Maple Leafs needed a reliable, steady presence in net. So, he signed the NHL's oldest goaltender to a 3-year, $21 million deal in free agency.
Bobrovsky is coming off the worst season of his career. However, he is a multiple Stanley Cup and Vezina Trophy winner who has played fifty-plus games in 11 of his 16 NHL seasons. He must give the Leafs a year or two of league-average or better goaltending to justify their investment.
1. Auston Matthews
Despite all the talk about the Maple Leafs' shiny new toys, it's Matthews who holds the key to a Toronto revival. After two injury-marred, subpar seasons, the Leafs' captain will face serious questions should he and the team falter again.
Matthews needs to stay healthy and return to his place among the NHL's most feared goal scorers. He is under pressure to stop his regression and re-establish himself among hockey's elite players. A third straight down season would bring questions about his future in Toronto with only two years remaining on his current deal.
Whether it is justifying a massive contract, returning to previous glory, or surviving intense media scrutiny, the pressure may reach a boiling point for Matthews and the rest of these Maple Leafs players during the 2026-27 season. The hot seat is officially occupied, and how these five individuals respond under the microscope will ultimately dictate whether this roster can achieve playoff glory or if Chayka may be forced to trigger more major roster changes.
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