Tuukka Rask
Finally, we have perhaps the biggest mistake that the Leafs made in perhaps the history of the franchise.
With Toronto moving on from Ed Belfour following the 2005-06 campaign, the Leafs needed a proven starting goalie ahead of the 2006-07 season. In their search for a No. 1 goaltender, Boston Bruins Andrew Raycroft caught their eye as he was a former Calder Trophy winner back during the 2003-04 season.
Having fallen out of favour in Boston, the Leafs jumped on what they though was a fortuitous opportunity to work out a trade for Raycroft with the Bruins. With the choice of including either goalie Justin Pogge or first round pick Tuukka Rask as part of the return, Toronto decided on Rask, given Pogge was coming off a spectacular 38-win season with the WHL Calgary Hitmen and a gold medal win from the World Juniors Hockey Championship.
That fateful decision has ended up haunting the Leafs for almost to the end of eternity ever since. For Raycroft, he would post two underwhelming seasons with Toronto despite putting up 39 wins in total. For Pogge, it was even worse as he would appear in just seven games for the Leafs for his entire NHL career.
As for Rask, he would eventually become a mainstay in the Bruins net for over a decade, posting a stellar record of 308-165-66 with 52 shutouts, along with a lifetime 2.28 GAA and .921 save percentage. On top of that, he was part of the Stanley Cup winning team in 2011, he had captured the Vezina Trophy and was named to the NHL First All-Star team in 2014, along with the William Jennings Trophy and NHL second All-Star team in 2020. (All stats from hockey-reference.com)
More importantly, Rask would have been the solution to the Leafs net for pretty much the bulk of this part of the century, instead of circling through numerous failed options over the years. And if it wasn’t already bad enough that the Leafs made the wrong decision back then in who they gave up, it was learned later that the Bruins actually intended to release Raycroft prior to the trade.
So the Leafs could have even had Raycroft without giving up any assets at all. But instead, they gave away one of the best goaltenders to have played during the past two decades in the NHL. Painfully, without a doubt, Rask would have been a huge difference maker for the club in their Stanley Cup hopes all these years.