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 Picks for Phil Kessel in 2010
It’s always a gamble when you trade picks and, for the Leafs, this one didn’t pay off at all when the Buds grabbed Phil Kessel from the Boston Bruins in exchange for draft picks. Firstly, through a combination of poor play, poor scouting and bad luck, the Bruins were able to select Tyler Seguin with the second overall pick in the 2010 draft. Take another look at that 2010 draft if you get a chance, the Leafs only lose on this one if the Bruins draft Tyler Seguin or Taylor Hall; and the Bruins were able to take Seguin at number 2 after the Leafs skated to just 74 points in 2009-2010. Secondly, the Leafs’ scouts (and their fans) really never understood Phil Kessel as a hockey player. As a Leaf, he was a natural talent with zero drive – he’ll get you 35 goals, but he won't be your franchise player. By his own acknowledgement, Phil Kessel just likes playing hockey.
14 Randy Carlyle to the Penguins in 1978
Fun fact: no Toronto Maple Leafs blueliner has won a Norris trophy, but the Buds have given some away. In 1978, the Leafs traded defenseman Randy Carlyle (and forward George Ferguson) to the Pittsburgh Penguins for Dave Burrows (also a defenseman). Three years later, Carlyle would win the Norris Trophy and would continue to be one of the NHL’s best defenseman for the next 12 years. Dave Burrows? Although an All-Star before coming to Toronto, Burrows didn’t work out and was dealt back to the Penguins in 1980-81 (ironically the year Carlyle won the Norris) and retired thereafter.
13 Signing Jeff Finger in 2008
“Go on take the money and run” pretty much sums up the story of Jeff Finger and the Toronto Maple Leafs. In 2008, the Leafs signed Finger to a 4-year contract that paid him $3.5 million per season. Why? There is no rational answer to that question. Prior to the 2008 season, Finger had spent time in the East Coast and American Hockey Leagues before playing one full season with the Colorado Avalanche, where he grabbed a total of 19 points. After one and a half seasons with the Leafs, Finger was back in the AHL and, after his 4 years with the Leafs franchise were done, he was out of professional hockey altogether.
12 Picks for Vesa Toskala in 2007
Picks again, here we go. In 2007, the Leafs gave away their 1st and 2nd round draft picks (and a 4th rounder in 2009) to the San Jose Sharks for Vesa Toskala – picks that were later dealt to the St Louis Blues. In his two full seasons with the Maple Leafs, Toskala actually had a winning record on a team that was basically .500, though the rest of his stats aren't as passable. However, when you look to middle America, St. Louis took Lars Eller in the 1st round and Aaron Palushaj in the 2nd. Today, Toskala is retired and Palushaj has only played a handful of games in the Show, but Eller has proven to be a quality NHL center man with the Montreal Canadiens
11 First Rounder, Alan McCauley and Brad Boyes for Owen Nolan in 2003
At the time, this seemed like an unbelievable deal for the Leafs. Owen Nolan was arguably the best power forward in the NHL at the time and the Blue and White picked him up just prior to the 2003 playoffs. In Toronto, Nolan never looked like the player he was in San Jose. In the 2003 playoffs, he had just two points and, although he had a respectable 48 points in 65 games in 2003-2004, he would leave the squad after the lockout season in 2004-2005.
10 Signing Mike Komisarek in 2009
Prior to his arrival in Toronto, Mike Komisarek was an NHL All-Star with the Montreal Canadiens (albeit by fan vote). Again, like the Nolan trade, signing Komisarek seemed like a great idea at the time, as at $4.5 million a season for 5 years, the Leafs seemed on their way to solidifying their blueline with a shut down defenseman that could hit and block shots. Sadly, Komisarek, through a combination of injuries and unfulfilled expectations, was sent down to the AHL and later released by the Leafs as a free agent.
9 Doug Jarvis to the Canadiens in 1975
Alright, this one is particularly bad and, in hindsight, could be placed much higher on the list. After selecting Doug Jarvis in the 1975 NHL draft, the Leafs dealt him to Montreal in exchange for Greg Hubick. Here’s the rub. Jarvis went on to play 964 consecutive NHL games, as he didn’t miss a single game throughout his entire career. Additionally, Jarvis won the Frank J. Selke in 1984 and is widely considered one of the NHL’s best defensive forwards. Hubick, on the other hand, played one season with the Buds followed by four straight seasons in the CHL.
8 Kenny Jonsson and More to the Islanders in 1996
The Kenny Jonsson deal is tough to evaluate, even years later. In sum, the thought process here was to reclaim the heart of the team by bringing former captain Wendel Clark back to Toronto (who, despite his popularity, was actually part of one of the best transactions in Leafs history when he went to Quebec for Sundin). The breakdown of this transaction is as follows: Kenny Jonsson, Sean Haggerty, Darby Hendrickson and, here it is, a 1st round draft pick to the New York Islanders for Wendel Clark, Mathieu Schneider and D.J. Smith. Neither Jonsson nor Schneider played their best for the Buds, but were both excellent NHL blueliners throughout their careers, so we’ll call that a wash. Wendel Clark is awesome, period. And the other players in this deal are essentially non-factors. That draft pick turned out to be Roberto Luongo, which means the Leafs lost this deal handily.
7 First Rounder (Scott Niedermayer) for Tom Kurvers in 1989
It’s been well established here that the Leafs, for whatever reason, love to give away draft picks. Coupled yet again with poor foresight, this 1st round pick was for the 1991 draft, which brought Tom Kurvers to the Leafs. That draft, which included: Lindros, Forsberg, and Niedermayer would come back to haunt the Buds big time. At number 3, the New Jersey Devils selected Scott Niedermayer and the rest is - well, history. Niedermayer went on to hoist four Stanley Cups, a Norris Trophy, and a Conn Smythe Trophy in 18 NHL seasons. Additionally, he won two Olympic Gold Medals in 2002 and 2010 (where he captained the Canadian squad). In the unlikely event that you’re wondering what happened to Kurvers, he lasted two seasons with the Leafs and played on seven NHL teams over his 11 years in the league.
6 Ken Wregget to the Flyers in 1989
In 1989, the Leafs dealt proven goaltender Ken Wregget to the Philadelphia Flyers in exchange for two 1st round ricks. Therefore, in 1989, the Maple Leafs had three 1st round draft picks: the 3rd, 12th, and 21st. Mats Sundin was the Quebec Nordiques’ 1st overall pick, which left names like: Guerin, Foote, Lidstrom, and Federov as potential Leafs. With the third pick, they took Scott Thornton and with the two Philly picks they took Rob Pearson and Steve Bancroft. And despite actually trading “for” picks, which is a rarity, the Leafs lost on this one too. Ken Wregget would provide steady netminding to both Philly and Pittsburgh over the next 10 seasons, grabbing a Cup with Pens in 1992, while all of three of those picks would come nowhere near their expectations.
5 Tuukka Rask to the Bruins in 2006
In 2006, the Leafs traded Tukkaa Rask, their 2005 first round pick (21st overall), to the Boston Bruins for Andrew Raycroft. The following pretty much sums up how this trade turned out for the Leafs: the starting goaltender in the 2016 Winter Classic for the Bruins was Tuukka Rask, while Raycroft was between the pipes for the Bruins in the 2016 Winter Classic Alumni game. Rask also won the Vezina Trophy in 2014 while Raycroft was playing out his career in Sweden.
4 Russ Courtnall to the Canadiens in 1988
After exciting Leafs’ fans for six seasons with his speedy wheels alongside Wendel Clark and Gary Leeman on the “Hound Line,” Russ Courtnall was dealt to the Montreal Canadiens for tough guy John Kordic. No doubt that NHL teams need (or did need) enforcers. And had Courtnall not gone on to be such a solid NHL player for the next 11 seasons, this transaction would look much better. However, Kordic was out of the league four years after this deal was made and, to be frank, was a very forgettable Maple Leaf.
3 Lanny McDonald to the Rockies in 1979
Sending Lanny McDonald to the Colorado Rockies, or anywhere else for that matter, made absolutely no sense. However, this transaction did bring #99 to the Maple Leafs. No, not “that” #99 - the other one, Wilf Paiement. In December of 1979, Lanny McDonald along with Joel Quenville left for the Rockies and the Leafs grabbed Wilf Paiement and Pat Hickey in return. McDonald would eventually score 66 goals in 1982-83 (which places him in very select company) and lift the Stanley Cup with the Calgary Flames in 1988-89, while the two players acquired by the Leafs did nothing of note.
2 Darryl Sittler to the Flyers in 1982
What’s worse than trading away Lanny McDonald? Trading away Darryl Sittler. Anyone who spent his or her youth as a Leafs’ fan in the 70s is well aware that there wasn’t much to cheer about. However, there was Darryl Sittler, the captain and certainly one of the most beloved Toronto Maple Leafs players of all time. In 1982, after a couple of years of feuding with Leafs’ management, Sittler was dealt to the Flyers for a mixed bag of Rich Costello, a 1982 2nd round pick, and future considerations. This transaction was a total loss on all fronts. The Leafs gave away their most popular and best player and in return picked up a career AHLer in Costello and the draft pick turned out to be Peter Ihnacak, the definition of NHL mediocrity.
1 Bernie Parent to the Flyers in 1973
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.