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Top 15 Worst Moves in Toronto Maple Leafs History

The Toronto Maple Leafs are undeniably one of the most storied franchises in the history of the National Hockey League and, more generally, one of the most financially successful professional sports franchises. From 1918 to 1967, the Buds won 13 Stanley Cups while competing in 21 Cup Finals. However, in the interest of both honesty and reality, after 1967, which is closing in on 50 years, the Leafs are the lone Original Six team not to hoist the Cup in the NHL’s post-expansion era. The Montreal Canadiens, for example, have won 10 Stanley Cups after 1967. And despite a half-century of losing, the Toronto Maple Leafs continue to be a massive, financially successful franchise with an incredibly loyal fan base.

Why so loyal? Firstly, it’s Toronto and it’s hockey. Secondly though, during those post expansion years in the 70s, 80, and even into the 90s, the Leafs always seemed to have that one player (or in some cases two) that kept the team respectable, even when they were horrible. Names like Sittler, Salming, MacDonald, Vaive, Gilmour, Clark and Sundin gave Leafs’ fans a sense of hope while following a franchise that was truly going nowhere fast.

What makes the Toronto Maple Leafs such an intriguing organization is their track record for being on the short end of so many transactions. In fact, save perhaps the deals that brought Gilmour and Sundin to Toronto in 1992 and 1994 respectively, the Leafs’ brass, from Ballard to Ferguson to Burke, have given away, in players, prospects and money, far more than they have gotten back. What’s even more remarkable is that, notwithstanding the recent overhaul of the Leafs’ front office to appease a disgruntled fan base, Toronto is still considered the hockey capital of the planet. Time will tell if Shanahan, Babcock, and Lamoriello can rewind the historical tape and return this franchise to its former glory. In the meantime, we can take a look what has occurred between 1967 and the present – The Worst Moves in Toronto Maple Leafs History.

15 15. Picks for Phil Kessel in 2010 

Greg M. Cooper-USA TODAY Sports

14 14. Randy Carlyle to the Penguins in 1978 

via suddendeathhockeyforums.ca

13 13. Signing Jeff Finger in 2008 

via thestar.com

12 12. Picks for Vesa Toskala in 2007 

via thehockeyhouse.net

11 11. First Rounder, Alan McCauley and Brad Boyes for Owen Nolan in 2003 

via thestar.com

10 10. Signing Mike Komisarek in 2009 

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9 9. Doug Jarvis to the Canadiens in 1975 

via vintagehockeycardsreport.com

8 8. Kenny Jonsson and More to the Islanders in 1996 

Robert Mayer-USA TODAY Sports

7 7. First Rounder (Scott Niedermayer) for Tom Kurvers in 1989 

via espn.go.com

6 6. Ken Wregget to the Flyers in 1989 

via the1jasontaylor.wordpress.com

5 5. Tuukka Rask to the Bruins in 2006 

Marc DesRosiers-USA TODAY Sports

4 4. Russ Courtnall to the Canadiens in 1988 

via 25stanley.com

3 3. Lanny McDonald to the Rockies in 1979 

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2 2. Darryl Sittler to the Flyers in 1982 

via grhosp.on.ca

1 1. Bernie Parent to the Flyers in 1973 

via betweentheposts.ca

What makes the Bernie Parent deal the worst transaction in the history of the Toronto Maple Leafs? Although there is no universal agreement on the subject, Parent is undoubtedly one of the top netminders of all time. The Leafs grabbed him from the Flyers in the 1970-71 season (after he had already established himself as an NHL goaltender) only to give him back to The City of Brotherly Love for a first rounder and Doug Favell two years later. Once back in Philly, Parent would go on to shelf two Stanley Cups, two Vezina Trophies and two Conn Smythe Trophies. To this day, Bernie Parent’s name echoes in reverence on Broad Street, as they chant “Only The Lord Saves More Than Bernie,” and his departure from Toronto in 1973 made for the Worst Transaction in Toronto Maple Leafs History.

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Top 15 Worst Moves in Toronto Maple Leafs History