Daily Faceoff's The Sheet host Jeff Marek recently sat down with NHL.com's Dan Rosen to dissect the Toronto Maple Leafs offseason and forecast the team's future. Like many prognosticators, they are not sure what to expect in the 2026-27 season.
Maple Leafs general manager John Chayka had a very busy first offseason in Toronto, trying to improve the team after missing the playoffs in 2025-26. He brought in defenseman Darren Raddysh in a sign-and-trade, drafted hot prospect Gavin McKenna with the first overall pick in the NHL Draft, and signed free-agent goaltender Sergei Bobrovsky from the division rival Florida Panthers.
Marek and Rosen discussed their concerns with Chayka's reconstruction of the Leafs and specifically mentioned both Bobrovsky and Raddysh. Yet neither was the biggest threat to sabotage the Maple Leafs' chances of success for the upcoming season.
Jeff Marek and Dan Rosen deconstruct the Maple Leafs' biggest obstacles
While many have praised Bobrovsky's conditioning and his ability to stay in great shape, Marek noted that Bobrovsky is the oldest goaltender in the NHL. Rosen added that his former team, the Florida Panthers, known for making all the right personnel moves, walked away from the Leafs' new goaltender. They signed Jacob Markstrom for just two years, at a $1 million lower AAV. Rosen also noted that Bobrovsky is coming off his worst season. He wondered if it was due to a combination of exhaustion and the Panthers underperforming because of injuries.
Rosen questioned if Bobrovsky is starting to decline. He also stated another Maple Leafs issue: its defense in front of the goaltender is not nearly as strong as Florida's. Marek then gave his thoughts on the Leafs' defense. He wondered, "Who is going to get the puck to (Auston) Matthews, and can they still improve this back end?"
Specific to Raddysh, Rosen called the Maple Leafs' new defenseman a "great story" but added, "Nikita Kucherov is not feeding him the puck anymore on the power play." He also pondered if Raddysh would be less of a focus on Toronto's power play with other shooters like Matthews and William Nylander.
Rosen described all of Toronto's offseason moves as "motion" and "didn't really move the needle forward." The NHL.com writer then gave his biggest hurdle for the Leafs. "The hardest part for Toronto, for me, is the division. Where do they stand in the division?" Rosen predicted five teams from the Atlantic Division will go to the playoffs.
"The hardest part for Toronto, for me, is the division. "Dan Rosen on the Leafs' biggest obstacle
He called the division "loaded." He predicted the only way a team from the Metropolitan Division gets a wild-card berth is if the Atlantic Division teams beat each other up. He listed Florida, Tampa, and Montreal as his favorites. The Maple Leafs are in a group with Buffalo, Boston, and Ottawa as teams with questions. Rosen explained the Leafs could finish fourth or fifth in the division, or they could finish in last place again.
Marek agreed that five teams from the Atlantic would make the playoffs this season, but The Sheet host queried: if Toronto makes the playoffs, which teams would be out? If both the Maple Leafs and Panthers return to the postseason in 2026-27, two Atlantic Division playoff teams from 2025-26 would be out.
Rosen's response was Ottawa. Captain Brady Tkachuk's loss could see them regress. He also wondered if Boston overachieved in 2025-26 and would fall back this year, and if Buffalo could repeat what they did last season. Marek countered that despite losing Bowen Byram and Alex Tuch, he still thinks the Sabres are a playoff team.
Over the past decade, getting out of their division has been a tough challenge for the Leafs. Since 2019, the Atlantic has had multiple Stanley Cup Finalists (7) and Cup winners (4). From Marek and Rosen's discussion, one thing is clear. The challenge of getting out of their division could sabotage the Maple Leafs' season.
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