Are the Toronto Maple Leafs in danger of repeating the Rask for Raycroft trade?

There’s an old quote attributed to NHL coach turned broadcaster Harry Neale that states, “Goaltending is 75 percent of your hockey team, unless you don’t have it. Then it’s 100 percent.” Over the last decade the Toronto Maple Leafs’ scouting team has taken this mantra to heart, selecting a goaltender in six of the last eight drafts, with the dividends finally beginning to payout at all levels of the organization. 

Joseph Woll continues to prove himself as a full-time NHLer. Dennis Hildeby has been the AHL’s best goaltender during his first season with the Toronto Marlies, posting a .943 save percentage across his first seven games. Artur Akhtyamov has been putting up some outstanding numbers during his first full season in the KHL, and Vyacheslav Peksa has left the Russian leagues to join the Newfoundland Growlers this season where he had a stellar 20 saves on 21 shots debut, before struggling over his next couple of games.

Combine this with some depth free agent signings such as Dryden McKay and Keith Petruzelli, and suddenly the Toronto Maple Leafs appear to have one of the best young goaltender pipelines across the NHL.

Another iconic quote exists that has less to do with hockey, but can still be applied. Winston Churchill once paraphrased Spanish philosopher George Santayana by stating, “Those that fail to learn from history are doomed to repeat it.” While it’s unlikely that Churchill or Santayana ever had to manage a hockey team, their lesson applies here.

Every Leafs fan can either vividly remember, or has heard countless horror stories about, one of the worst trades in franchise history – if not NHL history – when in June of 2006, the Maple Leafs decided to acquire third-year netminder Andrew Raycroft in exchange for the recently drafted Tuukka Rask.

To be fair to then-General Manager John Ferguson, there was some sense to the trade at the time. Raycroft was a Calder Trophy winner who had just gone through a rough sophomore slump and could be seen as a buy-low opportunity. Meanwhile, while Rask was putting up fantastic numbers in Finland, he wasn’t even seen as the best goaltending prospect in the Leafs organization, with Justin Pogge dominating at both the international and club level. In 2006 alone, Justin Pogge backstopped Team Canada to a World Juniors gold medal with a stunning .952 save percentage and 3 shutouts in 6 games while also recording a .926 save percentage with the Calgary Hitmen and winning not only WHL Goaltender of the Year, but also WHL Player of the Year and CHL Goaltender of the year.

Even though the Maple Leafs had just recently used a 2005 first round pick on Tuukka Rask, the 2004 third round selection of Justin Pogge seemed to have burst onto the scene as not just one of the Leafs’ best goaltending prospects, but one of the best prospects in all of hockey. Because of this, when Ferguson Jr went looking for immediate goaltending help in the summer of 2006, Rask seemed like the most expendable option available necessary to require the young and somewhat proven Andrew Raycroft.

The rest, as they say, is history. A tragic history for Leafs fans, and a memorable heist for the Boston Bruins who acquired one of the generations best goaltenders that would lead them to a Stanley Cup victory and playing over 500 NHL games, while Justin Pogge spent most of his career playing in Europe after failing to replicate his junior success as a pro.

Fast forward to 2023 and a similar story seems to be emerging. The Maple Leafs have had a decent, but by no means stellar start to the season. Much of their early season falters can be attributed to the struggles of Ilya Samsonov, who quickly lost his status as Toronto’s starting goalie to Joseph Woll.

If Samsonov continues to struggle, or if either netminder suffers an injury, then GM Brad Treliving may be forced to make a move. Especially when you consider that even with Woll’s excellence this season, having him play over 60 games is a non-option as the young goaltender has never appeared in more than 37 games at any level and nearly doubling that number in his first pro season risks significant injury and fatigue come playoffs.

While Marlies goaltenders Martin Jones or Dennis Hildeby will likely be given an opportunity, the temptation to make a trade for a bonafide starter will always be there, and any team trading away a proven NHL quality goaltender will likely ask for one of the Maple Leafs’ goaltending prospects in return. 

Even if Toronto doesn’t choose to acquire a goalie via trade, players like Hildeby, Akhtyamov, and Peksa are among the most valuable assets in the Maple Leafs’ system, and could be a key part of any in-season trade. If the Maple Leafs want to acquire a tough blueliner or scoring winger at the deadline to make a deep postseason run, then it’s very likely that at least one of those names are brought up during negotiations.

What comes next could very well define the tenure of this Maple Leafs management team top to bottom, from Treliving and Shanahan to every scout and coach. A goaltender who puts up good numbers is arguably the most valuable trade piece in the modern NHL, and the Maple Leafs currently have a few in the system who are putting up some of the best numbers in their respective leagues. 

If the Leafs trade away one of these young goaltending prospects for a difference maker that helps end the longest Stanley Cup drought in NHL history, then it was all worth it, and whether that goaltender flames out or becomes a superstar is irrelevant. But the risk of losing the next Tuukka Rask is always there, and having it happen a second time would only further prove that the Toronto Maple Leafs simply refuse to learn from their mistakes.

Brad Treliving was given a good team when he took over as Maple Leafs General Manager earlier this season. His job now is to turn that team from good to great, without destroying the future with yet another regrettable trade.