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Unfortunate Stat Line Highlights Maple Leafs' Worst Trade in Franchise History


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Nick Matthews
August 31, 2025  (4:25 PM)
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Tukka Rask
Photo credit: Sergei Belski-USA TODAY Sports

The worst trade in Maple Leafs history seems pretty obvious due to one statistic that almost certainly draws the ire of the entire fan base.

The Toronto Maple Leafs are heading into next season with a solid goaltending tandem of Joseph Woll and Anthony Stolarz.
However, goaltending has long been a controversial topic for the Leafs -- especially when it comes to developing their own prospects.
Back in 2006, Toronto made what is widely regarded as the worst trade in franchise history, dealing away goaltending prospect Tuukka Rask to the Boston Bruins in exchange for Andrew Raycroft.
The move has haunted the organization ever since. Adding to the sting, Rask went on to become arguably the best goaltender ever drafted by the Maple Leafs, despite never having played a game for them.
As per Marcussi_MA on X:
"In 2006, the Maple Leafs sent Tuukka Rask to the #NHLBruins in exchange for Andrew Raycroft.

Rask went on to record 308 career wins with Boston, the most ever by a goalie drafted by Toronto."
Rask carved out an outstanding NHL career, posting 308 wins across 564 games with a sparkling career 2.28 goals-against average and a .921 save percentage. He also captured a Vezina Trophy and hoisted the Stanley Cup with Boston.
For the Leafs, the lesson is clear -- patience with young goaltenders is essential. Today, the team boasts strong depth in the pipeline with Dennis Hildeby, Artur Akhtyamov, and Vyacheslav Peksa developing in the minors.
In the meantime, Toronto can rely on their current tandem of Woll and Stolarz. While goaltending appears stable for now, the organization will be reminded for years to come of the painful lesson learned from that two-decade-old mistake.
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Unfortunate Stat Line Highlights Maple Leafs' Worst Trade in Franchise History

Is the Tuukka Rask for Andrew Raycroft trade the worst in Maple Leafs history?

Yes69077.4 %
No20122.6 %
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