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Toronto Maple Leafs GM John Chayka has gotten off to a good start in cleaning up Brad Treliving's leftover mess.

Tuesday’s trade between the Toronto Maple Leafs and Philadelphia Flyers underscores one of John Chayka’s main tasks as GM: Pulling mop-up duty for Brad Treliving.

One of those blunders was extending Joseph Woll. In hindsight, it’s easy to see why Treliving extended both Woll and Anthony Stolarz. Their performance during the 2024-25 season, injuries notwithstanding, promised to be the beginning of a talented, if fragile goalie tandem. Woll’s three-year deal, carrying a $3.6 million cap hit, figured to be a steal for a starting goalie. Well, that deal aged really badly in a hurry.

As for Stolarz, last year was a dreadful campaign loaded with injury issues. Stolarz could not really keep himself on the ice long enough to really run with the starting role. Still, Treliving signed him to a four-year extension worth $15 million.

That situation put the Maple Leafs between a rock and a hard place. Add to that the emergence of Dennis Hildeby as a serviceable NHL goalie, and the Leafs had to figure out what to do with the relative abundance of netminders. The easiest target to go was Woll. Woll didn’t have any trade protection for this upcoming season. So, it had to be now that Chayka pulled the trigger on a move.

While Chayka could have waited a little longer, it’s likely this was the best deal he was going to get for Woll. And it ultimately could turn into a fleecing for the Maple Leafs. If Woll continues to have injury issues, the Flyers could be stuck with a talented but oft-injured goalie.

Treliving’s Efforts to Lock Up Maple Leafs Core Backfired

Treliving attempted to lock up what he perceived to be the Maple Leafs’ core. Woll was one of them. He believed in Woll’s potential despite the relatively small sample size. Still, it was enough to convince the team that there was something more to Woll. His performance in the 2024 NHL playoffs seemed encouraging despite the first-round elimination.

Woll was pressed into service when Stolarz went down last spring against the Florida Panthers. And to be fair, he almost pulled it off. He backstopped the Maple Leafs in the second round, holding the fort long enough to push the Panthers to a Game 7.

This season, unfortunately, Woll just couldn’t follow that up. Had he remained healthy and productive for the entire season, this conversation would certainly not be happening.

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Woll Proved He Couldn’t Carry Starter’s Load

Starting goaltenders are not asked to play 60 or 70 games nowadays. 20 years ago, goalies starting 60 games or more was par for the course. The backup was generally relegated to 20 starts at most during the regular season.

However, Woll proved he couldn’t carry the load for the Maple Leafs. During a stretch last November, Woll started eight games in a row. While he started fantastically well, he just ran out of gas. He eventually landed on the shelf again, considering he had missed the first month of the season while on personal leave.

All of that illustrates why Treliving made a bad bet. He believed that Woll would be the guy to lead the Maple Leafs to a new era of contention. Well, at least Chayka hit one out of the park by actually getting back value in a deal that had all the makings of a cap dump. It’s quite surprising Chayka didn’t just get a sixth-rounder for Woll.

But then again, that’s something the Treliving would have done.