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As the Maple Leafs face the end of a disappointing season, Keith Pelley has begun a comprehensive evaluation of the organization to determine if a front-office overhaul is necessary.

The Toronto Maple Leafs are preparing to embark on their final long road trip of the season as they get set to fly to St. Louis before a three-game set in California. But with no playoff aspirations, it appears it is not too early to start the process of determining what management will look like next season.

On the latest installment of TSN’s Insider Trading, Chris Johnston revealed that one-on-one conversations have already started within the Maple Leafs organization as they look to make some decisions. Johnston noted that this is a process MLSE CEO Keith Pelley has typically done with other MLSE sports entities, such as the Toronto Raptors and Toronto FC.

“But of course, when it comes to the Leafs, there's a little urgency to it," Johnston says. "And I should point out that Pelley hasn't limited his meetings to just within the organization, but is also meeting with people and picking the brains of people throughout the industry and throughout the league".

The urgency stems from the fact that Pelley has more than one major decision to make, starting with the General Manager position. Brad Treliving has one more year left on his contract, and Pelley must decide whether to stick with Treliving or make a change at the top.

After finishing last season with a 52-26-4 record and first place in the Atlantic Division, the Leafs struggled to find their game this year amid significant changes. This included the key off-season departure of forward Mitch Marner to the Vegas Golden Knights. Things went off the skids for Toronto following a three-week Olympic break; the Leafs have gone 4-8-4 since then, falling well out of the playoff race for 2026. Once officially eliminated, it will snap a playoff streak of nine consecutive seasons.

As Johnston mentioned, there are several decisions to make regarding the staff at the end of the season. The Leafs already made one minor staff change earlier in the year when, amid a struggling power play, they parted ways with assistant coach Marc Savard in December. Through games completed on March 26, 2026, the Leafs have a 31-29-13 record and sit seventh in the Atlantic Division, two points ahead of the two-time defending Stanley Cup champion Florida Panthers.