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Toronto Maple Leafs: 5 Biggest Trades in Team History

As one of the Original Six franchises in the NHL, the Toronto Maple Leafs naturally have one of the largest fanbases and are under the biggest microscope for any Canadian team. Over the years, the Leafs have made some great trades, while also making some moves that didn’t work out at all. With a very long history to pick from, what were the biggest trades in franchise history? Let’s break down the five biggest trades the Leafs have made.

Phil Gets His Ring(s)

Phil Kessel had come up with the Boston Bruins but entered his prime with the Maple Leafs when he was acquired in 2009. In his six seasons with Toronto, Kessel put up 394 points in 446 games as one of the team’s top scoring threats. With the franchise struggling, they decided that a prime Kessel was ripe for trade bait to help the rebuild.

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The result was Kessel being traded (along with Tim Erixon, Tyler Biggs and a 2016 2nd round pick) to Pittsburgh in exchange for Kasperi Kapanen, Scott Harrington, Nick Spaling and two draft picks. The draft picks ended up not being much while the players Toronto acquired didn’t have an impact. Kessel, on the other hand, played four seasons with Pittsburgh where he won two Stanley Cups and put up 303 points in 328 games.

No Niedermayer

At the beginning of the 1989-90 season, the Maple Leafs traded away their 1991 first round draft choice to the New Jersey Devils in exchange for veteran defenseman Tom Kurvers. Kurvers started his career with Montreal before moving to Buffalo and then New Jersey where he was a fine player, but not great.

The move didn’t help the Maple Leafs at all, as they were one of the worst teams in the NHL and only got 89 games out of Kurver before sending him to Vancouver. Meanwhile, that first round pick became the third overall in the 1991 NHL Draft, which the Devils used to select Scott Niedermayer. Niedermayer would end up having a Hall of Fame career with a Norris Trophy, four All-Star Team selections and four Stanley Cup wins.

The Tuukka Mistake

In 2005, the Maple Leafs drafted Finnish goaltender Tuukka Rask, the top rated goalie prospect from Europe, with the 21st overall pick. However, the Leafs felt like they already had their “goalie of the future” with Justin Pogge. With that, they sent Rask to the Boston Bruins before he played an NHL game, acquiring Andrew Raycroft to be their goalie until Pogge was ready.

Raycroft spent just two seasons in Toronto, posting a records of 39-34-14 before signing with teh Colorado Avalanche in 2008. Rask, on the other hand, became a staple in Boston for many years, winning a Vezina Trophy to go along with his multiple All-Star nods. Perhaps Rask could’ve been the one to get the Leafs over the hump during the 2010s.

Sundin Comes To Toronto

Mats Sundin was a quick star with the Quebec Nordiques after making his debut in the 1990-91 season. After four years with the team, though, the Maple Leafs came calling and acquired the eventual Hall of Famer along with Garth Butcher, Todd Warriner and a first round pick. In return, they sent Wendel Clark, Sylvain Lefebvre, Landon Wilson, and a first round pick to Quebec.

Sundin spent 13 total seasons in Toronto, putting up 987 points in 981 games. Though he didn’t win a Stanley Cup, Sundin was the biggest star for the Leafs, becoming a franchise legend in the process.

The 1992 Calgary Blockbuster

By January 2, 1992, Doug Gilmour was already one of the best defensemen in the NHL after spending several seasons with St. Louis and Calgary. Then GIlmour was involved in the biggest trade in NHL history at the time with 10 players involved. Gilmour was acquired by the Maple Leafs along with Jamie Macoun, Kent Manderville, Ric Nattress, Rick Wamsley. 

Meanwhile, the Flames acquired Craig Berube, Alexander Godynyuk, Gary Leeman, Michel Petit, and Jeff Reese. Of course, Gilmour was the centerpiece of the trade, spending seven different seasons in Toronto during his Hall of Fame career. Gilmour posted 452 points in 393 games, winning a Selke Trophy in the process.

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