Former Bruins GM revisits worst trade in Maple Leafs history

The Toronto Maple Leafs and Boston Bruins had frequently been trade partners during this part of the century. However, for whatever reason, it just seemed like each time, the Bruins would outright win the trade while the Leafs often being left with the short end of the stick. Whether it be the Phil Kessel debacle back in 2009 that ended up giving Boston Tyler Seguin and Dougie Hamilton, or the more recent Brandon Carlo laugher that made Toronto cough up top prospect Fraser Minten AND a first and fourth round draft pick, the Leafs always handed the Bruins a plethora of riches.

Well, despite all of that, none of them likely even measures up to what perhaps could be the worst Maple Leafs trade in the history of the franchise in the Tuukka Rask for Andrew Raycroft, one-for-one deal back during the 2006 offseason. The straight swap of two goaltenders that set the Leafs back a decade.

It was so bad that even former Bruins GM Jeff Gorton had to bring it up again during the hockey podcast Agent Provocateur with hosts Allan Walsh and Adam Wylde.

Maple Leafs certainly had a hard time recovering from Tuukka Rask trade with Bruins

So Gorton brought up the fact that the Bruins were in the midst of a rebuild in the mid-2000s with many moving parts at the time. But the big one that stood out to him was the massive trade of goalies between the Maple Leafs and the Bruins that ultimately changed the landscape for both clubs in the end. More significantly was the fact that Boston made the right decision on the goalie of pursuit.

“The trade with Tuukka … they (Toronto) had given us a choice of (Justin) Pogge or Tuukka. And I’m happy that we picked the right one,” Gorton said. “It was great for the Bruins, it was good for my career probably, and maybe not good for you as a fan of the Leafs.”

Practically everyone, except the Maple Leafs, came out great from the deal. The Bruins ultimately became contenders again as Rask eventually took over the reigns in net after Tim Thomas. For Rask himself, he was a two-time NHL All-Star, along with winning the Vezina trophy as the league’s top goaltender in 2013-14 and the William M. Jennings trophy alongside fellow netminder Jaroslav Halak in 2019-20 as the top goaltending duo in the NHL. Not to mention winning the Stanley Cup as a backup in 2011, as well as reaching the finals another two times in 2013 and 2019.

Had Toronto held on to Rask and dealt Pogge instead without giving Boston the choice, who knows how their paths would have went from there on out. Obviously, the Leafs ended up failing miserably with Raycroft and Pogge. Raycroft would have one decent season with the Leafs in 2006-07 in which he posted a 37-25-9 record with a 2.99 GAA and .894 save percentage in 72 games played that year. However, he would be gone after the following season after a disastrous 2007-08 campaign with the Maple Leafs. As for Pogge, his Leafs and NHL career would last all of seven games in 2008-09, as he would end up heading overseas after a few years in the AHL just to resurrect his professional hockey career.

Leafs fans everywhere all knew it was a monumental trade that one would rather forget. But Gorton, of course, just innocently and casually had to bring it up again just to make sure the sting hurt just a little longer. Nevertheless, maybe it’s a good lesson that the Maple Leafs should learn to avoid the Bruins at all costs with respect to any trade in the future.

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