For much of the last decade (and you could easily argue, the ones preceding it), the Toronto Maple Leafs have found unique ways to torture their fans.

Through heartbreaking playoff losses, star players leaving the franchise, and more twists and turns than an M. Night Shyamalan thriller, cheering for the Leafs isn’t exactly for the faint-of-heart.

But in case you haven’t been that tuned in recently, rock bottom might still be on the way for the Leafs, who are in the midst of their worst season in years, as they sit dead last in the Atlantic Division and are on pace for just 77 points.

A pair of trades made last season by Toronto could end up haunting the team, with the Leafs’ short-term playoff push potentially proving harmful for their long-term outlook.

Last year, the Leafs made trades with the Boston Bruins and Philadelphia Flyers, picking up defenceman Brandon Carlo and forward Scott Laughton.

The motivation behind the trades made sense at the time, even if one could argue about the process. Toronto was facing an uncertain future with star forward Mitch Marner, and was putting in all their chips to push for a long playoff run, eventually falling to the Stanley Cup champion Florida Panthers in Game 7 of the second round.

But the risk of the trades seems to have a big chance to haunt the Leafs. Even disregarding the fact that both players have missed games due to injury this season, what they gave up in those trades is something the Leafs could certainly use in a tough season.

The Leafs won’t have first-round picks in 2026 (traded to Boston for Carlo) or 2027 (traded to Philadelphia for Laughton), unless their 2026 pick is top-five or their 2027 pick is top-10, due to conditions of each trade.

Toronto also parted ways Fraser Minten in the Bruins deal and Nikita Grebenkin in the trade made with the Flyers.

If Toronto falls into the top-five of next spring’s draft lottery, they’ll have the option to bump their draft pick trades back a year, meaning they’d still be able to land a top prospect. But if the pick lands sixth or later, they’ll be forced to part with it.

Either way, Toronto will be without two first-round picks in the next three years, in a time where they could be using them to help with a rebuild. And if those picks end up turning into productive NHL players (or even, heaven forbid, star players), Leafs fans won’t likely stop wondering what could’ve been anytime soon.

Lead photo by

Dan Hamilton/Imagn Images