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Darren Dreger suggests the Maple Leafs have another big move on the way


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Alexander Cole
September 29, 2026  (7:20 PM)
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Toronto Maple Leafs general manager John Chayka speaks to the media during an introductory news conference at Real Sports Bar.
Photo credit: Dan Hamilton-Imagn Images

The Toronto Maple Leafs may not be finished reshaping their roster. TSN insider Darren Dreger appeared on OverDrive and teased that the club "might not be done," then urged listeners to tune into Insider Trading for the full breakdown.

The timing makes the tease even more intriguing. Toronto has already overhauled its forward group by sending Matthew Knies to Columbus for Kirill Marchenko.
Earlier in the day, Dreger explained that the deal was a lengthy negotiation between Blue Jackets general manager Don Waddell and Leafs general manager John Chayka.
Marchenko's extension was completed as part of the trade, and Toronto is now waiting on immigration paperwork to learn whether he can debut in the home opener against the Montreal Canadiens.

Why Another Trade Would Not Be Shocking

Chayka has shown he is willing to act decisively. After the Leafs missed the playoffs in 2025-26, the pressure to improve has been obvious.
Parting with a homegrown winger like Knies proved that no one on the roster is truly untouchable, and that mindset opens the door for more activity.
Dreger did not name a target in the teaser, so any speculation should stay measured.
Still, several situations around the league remain unsettled, including Connor Hellebuyck's future in Winnipeg and Dylan Larkin's status in Detroit, both of which Dreger addressed in his earlier segment.
Whether either connects to Toronto is unclear, but a hint from a well-sourced insider rarely comes out of nowhere.

What Leafs Fans Should Watch Next

First, keep an eye on Marchenko's status for the opener, since his arrival shapes how Toronto's lineup looks against Montreal.
Second, watch Insider Trading for any specifics on what Dreger is hearing, including whether the next deal involves a forward, a defenseman or a goaltender.
Third, monitor how the Leafs balance cap space and roster spots if another transaction materializes.
For now, the message from Dreger is simple: Toronto's busy stretch may not be over. Chayka has already surprised the league once, and another big swing would fit the pattern he is building.
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Darren Dreger suggests the Maple Leafs have another big move on the way

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