John Chayka has executed his first trade as GM of the Toronto Maple Leafs, sending goaltender Joseph Woll and defenseman Simon Benoit to the Philadelphia Flyers in exchange for goaltender Samuel Ersson, left-shot defenseman Emil Andrae, and a third-round pick in 2026.
Well, the Leafs‘ goalie domino has dropped.
Following a season in which Dennis Hildeby played well at the NHL level and Artur Akhtyamov put together a very good AHL campaign, the Leafs were always likely to move a goalie. Hildeby could no longer be sent down to the AHL without passing through waivers, where he likely would have been claimed. Joseph Woll was the easiest of the group to move; he had no trade protection and some pedigree around the league, compared to Anthony Stolarz’s 16-team no-trade clause.
There are two parts to this trade to discuss: was Woll the right goalie to trade, and what about the return?
As part of the deal, the team also moved off the final year of Simon Benoit’s contract. Clearing the cap space is not a particularly big deal, as the Leafs have plenty of cap room, and even if they waived Benoit, he would have counted for only $200K against the cap. Clearing the roster spot, however, was noteworthy. The Leafs had all seven of their defensemen from last year under contract heading into the offseason, and there was no world where they could have returned with that same unit. They had to move a defenseman at some point, and it started with Benoit, who really struggled after signing a three-year deal and, in some ways, represented a broader issue of the team prioritizing size over any ability to move the puck.
In terms of moving Woll, he was always going to be the easiest goalie to trade. He has been very good at times, has a reasonable cap hit, is only turning 28 this summer, and has zero trade protection to work around.
For Woll, it has never been a question of talent. It has always been about his dependability. He stepped away from the team at the start of this past season and played just 39 games total. The season before that, he got hurt and played 42 games. Before that, he suffered an injury attempting a save in the final second of Game 6 when the team held a multi-goal lead. He missed Game 7, though he did not require surgery or anything significant from the injury. Generally, most would agree he’s a good goalie when healthy, but you couldn’t fully rely on him.
While I’d argue Anthony Stolarz is more talented—and significantly better at playing the puck—he is also more unreliable and four years older. Stolarz has played more than 30 games just once in his career.
Considering this is Woll’s return, you can see how difficult it would have been to move Stolarz. Given the Leafs took on positive value—a decent young defenseman and a third-round pick—while also dumping Simon Benoit, the alternative may have been having to pay to move Stolarz, if anything.
Moving forward, if the Leafs are going to roll with younger, unproven goalies like Hildeby or even Akhtyamov — which is likely — then they want a steady and reliable veteran anchoring the position throughout the season. Stolarz is talented when he is in the lineup, but he is completely unreliable, arguably even more so than Woll at this point.
That is where the crux of this deal comes into question. The Leafs want to be good next season, and while they have legitimate talent in net, they cannot rely on a single option. If the goaltending goes up in flames because Stolarz keeps getting hurt and plays around 25 games while the younger options are not ready to carry the workload, it would sink their season regardless of what else they do.
They did acquire Samuel Ersson in the deal, who is a goalie, but he has not shown well at any point in North America, and you could argue they should simply not qualify him rather than sign him to be part of their mix. It’s hard to view him as reliable veteran insurance in this case.
The noteworthy piece of the return is Emil Andrae. He is a pending RFA, and AFP Analytics projects a two-year deal for him at just over $2.1 million per season.
Naturally, his size — 5’9″ — immediately stands out. That likely limits his overall upside, but he has shown well as a third-pairing defenseman in the league.
In an upcoming write-up on RFAs to target, Andrae was on my list. The production has not been there, but he is a good puck mover who can break out and make plays with the puck. It is hard to overstate just how bad the Leafs’ defense was with the puck last season. Not only could they not break out cleanly, but they could not make plays with the puck, whether it was Benoit, Philippe Myers, or Brandon Carlo, who represented a significant portion of their regular defensive group. Andrae at least adds mobility and puck movement, and he won his minutes last season 36-22. On a Flyers team that was +12 overall at five-on-five, that means they actually lost their minutes at five-on-five when Andrae was not on the ice.
Andrae accomplished that while playing just 15:20 per night, so it is fair to question whether he has much more upside than being a third-pairing player. At this point, however, if the Leafs can get him to be a third-pairing defenseman who can move the puck and win his minutes, that is a significant improvement over what they ran out there last season. Again, it is almost impossible to overstate just how poor the Leafs’ defense was with the puck.
Even if Andrae does not progress beyond a third-pairing player, the other question is whether he can progress offensively. He was stuck behind two other smaller defensemen, Jamie Drysdale and Cam York, whom the Flyers have invested heavily in. Andrae was never going to pass them on the depth chart, and he averaged just 23 seconds per game on the power play, fifth among Flyers defensemen. Right now, his competition in Toronto is Morgan Rielly and OEL, two players he likely will not pass either, but there is a clearer path for him to get a chance and show what he can do. That may be particularly true if there is more surgery to come on the backend, with Rielly’s name at the center of trade speculation.
The third-round pick should not be dismissed, either. For all the talk about the Leafs not owning any trade assets, after they draft first overall this season, they will have a full draft class that includes extra selections in the third and fifth rounds, with no seventh. Next season, they own a pick in every round except the third and seventh, and they also own two second-round picks and two sixth-round picks. When we also consider their ample cap space, the organization does have assets they can use to take on good but overpaid players and make deals if they choose to.
It is ultimately a disappointing return for Joseph Woll, who once looked like a potential 1A goalie for the club. We are talking about an undersized third-pairing defenseman, a third-round pick, and clearing the final year of Benoit’s contract. If Woll continues to struggle with injuries and misses significant time, and/or the other Leafs goaltenders prove capable of carrying the workload, it should turn into a pretty good trade for the team. If the goaltending craters because of Stolarz’s continued uncertainty while Woll remains a solid tandem goalie and Andrae struggles to stick as an everyday player, this is going to age poorly as John Chayka’s first move.
The range of outcomes is pretty drastic, but you can see the Leafs are pushing toward a youth movement in net and on defense, with a greater emphasis on puck movement.
