John Chayka took six weeks to make his first big change to the Toronto Maple Leafs roster — and it was a doozy.Out go Joseph Woll and Simon Benoit, and in come Swedish defenceman Emil Andrae, goaltender Samuel Ersson (maybe) and a third-round pick in the upcoming draft.Was it a good first trade for the new Leafs GM? A smart first trade? That depends on a lot, which we’ll get to.The only thing we can say for sure right now is that it’s a huge roll of the dice.The Leafs are set to enter next season with a crease of Anthony Stolarz, Dennis Hildeby and Artur Akhtyamov — a fraught and inexperienced combination for a team that is desperate to get back to the playoffs.With Woll gone and two inexperienced options in his place, the Leafs stand to become even more dependent on Stolarz. And if his short tenure in Toronto has proven anything, it’s that too much too often is trouble for the 32-year-old.Stolarz broke down after only 12.5 starts last fall, with Woll on a leave of absence. He ended up starting just 25 games because of injuries and has missed time with one issue or another throughout his NHL career.He has never started more than he did in his first season with the Leafs, when he played 33 games while also missing a chunk of time with a knee injury.Injuries have to be expected at this point.Which means that, in reality, the Leafs can probably only count on him to make 25-30 starts. Anything more would be a bonus.Which means filling in the rest — upward of 50 starts — with Hildeby and/or Akhtyamov (or perhaps adding a more experienced netminder of some kind).The excitement over the two young goaltenders is understandable. And Chayka noted, shortly after the trade was announced, that the play of both “causes you to take notice.”But in both cases, it’s dicey to read too much into anything they’ve done to this point.Hildeby was certainly impressive last season, but made only 14 starts. He has started 20 NHL games, total, in his career.The Leafs likely need him to double that next season. As Stolarz has shown, maintaining a high level of performance gets that much harder when the workload increases — from starting maybe once a week to two, three and maybe even four times.Dennis Hildeby played well last season, but only made 14 starts. (Vaughn Ridley / Getty Images)It’s almost a sure thing that Hildeby and Akhtyamov will share the crease at some point next season — one injury away from what would, presumably, be the most inexperienced crease in the NHL.What Akhtyamov can provide at the NHL level is a giant mystery at this point, even with his sparkling run for the Marlies during their unexpected run to the Calder Cup final. Goalies are a mystery box that way. It wasn’t that long ago that Garret Sparks cooked the AHL en route to a Calder Cup, only to crash out in the NHL.Of course, there’s a chance that one or both of Hildeby and Akhtyamov rise up and shine next season and beyond.But did the Leafs and their new GM need to take that chance with so much on the line — Auston Matthews’ long-term future with the team in question above all?Woll was far from perfect. He got hurt a lot and never felt like the most reliable goaltender because of it. This was never more apparent than in the 2024 playoffs when Woll was suddenly unavailable to play in Game 7 against the Bruins because of injury.He still has yet to start more than 41 games in an NHL season and will turn 28 later this summer.Yet, Woll was the most proven goaltender the Leafs had, with growth potential still in the cards.Woll won more games than any Leafs goaltender over the last four seasons and played two of the best games of the bunch before that injury in 2024 — gems that kept the Leafs’ season alive in Games 5 and 6 against the Bruins.He has a career save percentage of .906 and the 31st-ranked cap hit ($3.67 million) among NHL goaltenders next season.In trading him, Chayka is betting that either Hildeby or Akhtyamov can deliver a similar level of performance for less. He might be proven right in the long term, but Woll looks clearly like the better bet in the short term.And the Leafs, with none of their own first-round picks in 2027 and 2028, need short-term performance in goal.Chayka didn’t offer much in the way of explanation about why Woll was the guy to go, though he was clearly the one with the most (any?) trade value.The Leafs GM explained that the team wanted to leverage the depth it had in goal and “create flexibility and accrue some assets — young assets too.”“We think flexibility and optionality are assets to any great organization,” Chayka said.By which he meant cap space and what he described as added roster flexibility, “just with how the profile of Emil lines up with some of the other players that we’re looking to add or are part of our roster currently.”In other words, the Leafs were able to add a young defenceman on the left side in an offseason that may see a longtime stalwart there, Morgan Rielly, moved in a trade.Andrae, he said, is a “smart, competitive player” who would give the Leafs more puck-moving pop and offensive prowess (traits the team will require even more so if/when Rielly is dealt). And he is only 24, youthful by any measure but especially on a defence stuffed with 30-plus types.There was also that draft pick, another asset to play with for the GM — either in a trade or as another prospect for a pool that needs help.“From my (standpoint), having options and having flexibility, I think, is undervalued, candidly,” Chayka said, “and for us, I think it sets up very well for future moves.”Zoom out, though, and the Leafs have swapped their No. 1 goalie for an intriguing defenceman, but a third-pairing defenceman essentially, and a mid-round pick. Ersson, a pending RFA, may or may not be qualified.That’s a tough move to justify, especially for a team that wants to contend next season and didn’t necessarily have to do anything in goal.Was losing Hildeby for nothing, potentially, next fall worth what was gained here, including the added cap space for a team that already has plenty of cap space?If this was the best the Leafs could do with their most attractive trade asset in goal, they may as well have stood pat and let things play out.Instead, they are rolling the dice in three ways:They’re betting that …1. A crease of Stolarz, Hildeby and Akhtyamov will be good enough to get the Leafs to the playoffs next season.2. Andrae, a pending RFA this summer, can add much-needed spice to the bottom of their blue line (a reasonable bet).3. One of their young goalies will be better than Woll now and later.It’s possible Chayka will be proven right on one or all of those fronts, that he’ll be proven shrewd for getting out in front of this. Or, if he’s wrong and the Leafs miss out on the playoffs next season and goaltending is a problem, we’ll look back on this as the first unforced error from the new Leafs GM.