The Toronto Maple Leafs made what they perceived was a win-now deal for defenseman Brandon Carlo at the 2025 trade deadline.
It turned out to be more of a lose-indefinitely deal.
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Toronto is at risk of losing its first-round pick in the 2026 NHL Draft depending on how tonight's NHL Draft Lottery shakes out. If the Maple Leafs' pick falls outside the top-five, they'll send their selection to the Boston Bruins as part of the Carlo deal.
Let's get into how the Maple Leafs got here and what their draft lottery night could look like.
The franchise-altering trade
Toronto was among the NHL's best teams by the 2025 trade deadline and was looking to add the right piece to get Auston Matthews and Co. over the dreaded playoff hump. The Leafs reportedly considered Rasmus Andersson, Mikko Rantanen, Luke Schenn and Rasmus Ristolainen before ultimately landing on Carlo, whose time in Toronto has been underwhelming and injury-ridden.
In exchange for Carlo, Toronto gave up forward Fraser Minten, a 2025 fourth-round pick and a top-five protected 2026 first-round pick. Minten has since become a rising star in Boston, while the 2026 pick has a strong chance of landing somewhere in the 5-10 range.
How would Toronto keep its pick?
Toronto has the fifth-best odds at picking No. 1, so its chances of remaining in the top five are high but not rock-solid by any means. If it falls inside the top five, the Maple Leafs can begin their rebuild in earnest while giving the Bruins their first-round pick in either 2027 or 2028. The exact year is undetermined as Toronto also gave up a top-10 protected 2027 first-round pick in the Scott Laughton trade.
What's next for Toronto?
The future for the Maple Leafs is admittedly bleak. Rumors of Matthews' departure are swirling, the general manager hiring was widely panned and the draft pick situation is a mess. The Maple Leafs own the NHL's longest Stanley Cup drought at 59 seasons, and all indications are that won't change any time soon.
This article originally appeared on For The Win: 2026 NHL Draft: How Maple Leafs could lose 1st round pick after trade