Worst Leafs Trades Since 1967 Countdown – No. 1: Rask for Raycroft

Tuukka Rask is the all-time leader in wins among goaltenders drafted by the Toronto Maple Leafs. Every single one of those wins has been with the Boston Bruins.

After the 2005-06 season, it was clear that the Leafs needed a new starting goaltender. Despite boasting a strong offence, poor goaltending was a key reason why the Leafs came up just short of making the playoffs in the first season after the lockout.

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Father Time had clearly caught up with Ed Belfour, as the 40-year-old future Hall of Famer posted a .892 save percentage in 49 starts. Former top prospect Mikael Tellqvist clearly wasn’t the solution, as he had put together a .895 save percentage over 40 career starts. The de facto best option was journeyman J-S Aubin, who came in and put up a .924 save percentage in an 11-game heater down the stretch. But Aubin was a career backup, so buying into a small sample size like that obviously wouldn’t have been prudent.

Toronto had goaltenders in their system, but none of them were close to being ready to take over an NHL net.

There was Justin Pogge, Toronto’s third-round pick from the 2004 draft. Pogge was coming off an amazing season in which he posted a .926 save percentage for the Calgary Hitmen of the WHL and led Team Canada to gold at the World Juniors with a sparkling .952 save percentage in six games.

There was also Tuukka Rask, Toronto’s first-round pick from the 2005 draft. Rask had also put together a great 2005-06 season. He had a .926 save percentage in 30 games in Finland’s top professional league and he put together a .940 save percentage in six games at the World Juniors.

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As great as these prospects were, neither would be able to help the team in the immediate future. So general manager John Ferguson Jr. looked for a deal to make. He had his eyes on Boston’s Andrew Raycroft who, in 2003-04, just before the lockout, had won the Calder Trophy as the league’s top rookie and finished fifth in Vezina Trophy voting.

The Bruins were in a completely different situation than the Leafs when it came to goaltending. They had Raycroft, Tim Thomas, who came out of nowhere at the age of 31 and looked like a legitimate starting goaltender, and prospect Hannu Toivonen, a former first-round pick who had earned a look at the NHL level.

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Raycroft, like many players on the Bruins, had a rough time in 2005-06. The unexpected trade of captain Joe Thornton to San Jose shook the Bruins’ locker room. The team went from being a legitimate contender before the lockout to randomly trading away their best player and finishing fifth-last in the league.

Raycroft put up a .879 save percentage in 30 starts that season, struggling through injuries and ultimately losing the net to Thomas. As a result, Raycroft, just one season shy of winning the Calder Trophy, became expendable.

As much as we liked Andrew Raycroft, we knew he needed a fresh start somewhere,” Bruins general manager Jeff Gorton says, looking back at the situation in hindsight. “At that draft, we started shopping Andrew and Nick Boynton. Toronto right away had a lot of interest and they had two young goalies at the time that they were really high on and essentially gave us a choice of one of them for Raycroft.

That other goaltending prospect, of course, was Pogge, who had gained plenty of notoriety that year due to his amazing showing at the World Juniors. But Boston had wanted Rask for quite some time. At the previous draft, the Bruins were ready to take him with the 22nd overall pick, but the Leafs swooped in and picked him just one spot before that at 21st overall.

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So, this was a chance for Boston to finally get their guy. Rask would be a long-term project, but with Thomas in the mix, the Bruins had plenty of time to be patient. Toronto also supposedly had their guy. Raycroft was somebody who could help lift the team back into the playoffs after a disappointing season. Win-win, right?

Wrong. 14 years later, this is the most lopsided deal in Leafs history (since 1967), and it’s only getting worse.

Raycroft was a flop for the Leafs. In his first season, he posted a .894 save percentage over 72 starts. Ironically, Raycroft tied a single-season Leafs record for most wins in a season, though that mostly came down to the volume of games he appeared in. Meanwhile, Justin Pogge, Toronto’s supposed goalie of the future, struggled in his first season as a professional with the Marlies.

As a result, the Leafs had to make another bad trade in the off-season in order to shore up their goaltending situation. They sent a first-, second-, and fourth-round pick to San Jose in exchange for Vesa Toskala, who ended up being yet another flop.

Raycroft would last just two seasons in Toronto before signing as a free agent with the Colorado Avalanche. Pogge would also go on to play just a handful of games in the NHL. Toronto would struggle through the enigmatic goaltending carousel of Toskala, Martin Gerber, a 41-year-old Curtis Joseph, Jean-Sebastien Giguere, Jonas Gustavsson, James Reimer, Ben Scrivens, and Jonathan Bernier before finally solidifying their net by acquiring Freddy Andersen from the Ducks in 2016.

In Boston, Rask would slowly but surely develop into the top goaltender than the Bruins had hoped he would become. He spent the 2006-07 season in Finland and then played two seasons for Boston’s AHL affiliate in Providence in 2007-08 and 2008-09. Finally, in 2009-10, he got called up and posted a .915 save percentage while splitting the net with Thomas.

The rest is history. Rask backed up Thomas as the Bruins won the Stanley Cup and then took over the net permanently soon after that. In 2013, he led the Bruins to the Stanley Cup Final after putting up a dominant showing against the Leafs in the first round. Again, in 2019 Rask took the Bruins to the Final, and, of course, that all started with a great first-round showing against Toronto.

All told, Rask has 291 wins, 50 shutouts, a .922 save percentage, a Vezina Trophy, a Jennings Trophy, and a Stanley Cup. When it’s all said and done, there’s a very good chance he’ll end up in the Hall of Fame.

This trade continues to haunt Toronto. Not only did they get completely hosed in the one-for-one value of the deal as Rask became a much better goaltender than Raycroft, but they also helped build the long-term future of their division rival. Rask now plays a key role in the reason why Toronto can’t make it out of the first round of the playoffs.