Toronto Maple Leafs: The Top 15 Biggest Mistakes in Franchise History

Brad LeClair@beerad87Correspondent IAugust 18, 2011

Toronto Maple Leafs: The Top 15 Biggest Mistakes in Franchise History

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    As we take a look back at some of the worst moments in Leafs history, we really don't have to look back too far. The terrible trades, terrible draft picks, letdowns in the playoffs and mostly some very bad hires have resulted in the Leafs' demise the past 40 years or so.

    In this article, I hope to outline the 15 worst trades, draft picks, signings and hires in Leafs history. I hope I can take a good consensus on the moves, and hopefully, I can get all of them.

    Without further interruption, it's time to take a stroll down memory lane.

15. The Hiring of Gord Stellick as Leafs General Manager

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    The youngest GM in franchise history, Gord Stellick, 30, seen here pondering a trade that would forever change the landscape of Leafs Nation.

    Stellick will best be remembered for his terrible trade of Russ Courtnall to the Montreal Canadiens for John Kordic. Courtnall was one-third of the Hound line that featured Gary Leeman and Leafs legend Wendel Clark.

    Kordic, on the other hand, was a known alcoholic with anger issues. Essentially, he was a drunken Colton Orr with a Marty McSorley like temper.

    Stellick, in conclusion, dealt a scoring winger for an enforcer, one of the worst moves a GM can make.

    The Leafs would finish 19th out of 21 teams and out of the playoffs with a paltry record of 28-46-6.

    Stellick, who was best known for standing-up to Leafs owner at the time Harold Ballard, had enough and announced his resignation in 1989, thus ending a pretty sad one year career as Leafs GM. He would get hired as an assistant GM with the Rangers, but was later fired in 1991.

14. Should We Retire Numbers, or Just Memorialize Our Legends?

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    This is likely the thing that irks me the most about the Leafs, and that is the fact they rarely retire number; rather, they memorialize and honor numbers instead.

    Countless franchises with storied pasts retire numbers, such as the Montreal Canadiens and New York Yankees for example.

    The Yankees only have two numbers up to nine still available to be worn. Derek Jeter wears the No. 2, and Joe Torre wore the No. 6. Both of these legends will likely have their numbers retired in due time after they retire.

    Anyway\, this way of doing things angered Leafs legend, and one of the top players ever to dawn a Leafs jersey, Dave Keon. Keon's No. 14 still isn't in the Leafs rafters as of yet, and the former captain is fine with that.

    Keon finished with 986 points in 1296 career games in the NHL. He was very small at 5'9" and 160 pounds, but his tenacity and ability on the ice was nearly unmatched. He, along with George Armstrong, helped lead the Leafs to their cup runs in the 1960's, something that hasn't happened in Leafs Nation since their departures.

    The Rouyn-Noranda native has rarely been seen around the Leafs since his retirement from the NHL.

13. Why Exactly Did Leafs Nation Boo Larry Murphy?

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    The Leafs who were in dire need of scoring on the back end decided to trade for Larry Murphy off the Pittsburgh Penguins. The Leafs sent a second round pick and Dmitri Mironov in return for Murphy.

    However, Murphy was the object of disapproval for Leafs fans, as he was booed mercilessly by Leafs Nation.

    Murphy was actually quite good initially with the Leafs, as he scored 60 points his first year with the Leafs, a feat only matched by few in a Leafs jersey. The last to do it was Bryan McCabe, and before McCabe, it was Al Iafrate.

    That wasn't good enough for Leans Nation as they booed him out of town, and the Leafs dealt Murphy to the Detroit Red Wings for future considerations.

    Adding to the rather rank odor of this deal, the Leafs were on the hook for 66.7 percent of Murphy's salary.

    Murphy is now a Hall of Famer and one of the best defencemen to play the game. In his rookie season of 80 games, he recorded 76 points! Murphy is seen here with his Hall of Fame class members Cliff Fletcher (left), Paul Coffey (immediate right) and Ray Bourque (far right).

    After the trade to Detroit, Murphy would close out his career with 52 points, 52 points, 40 points and 21 points in his final four seasons. One of the biggest mistakes in Leafs history here was booing this guy, despite his rather slow feet.

12. Acquiring Dmitri Khristich

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    Khristich was a decent NHLer for many years with the Capitals and Bruins. A six-time 25-plus goal scorer, Khristich had a knack for finding the back of the net. In his last season with the Bruins, Khristich scored 29 goals and added 42 assists for 71 points and a plus 11 rating.

    However, when he hit the Leafs, it seemed his career plummeted into the abyss, as he only scored 30 points in his first season with the club.

    The worst thing about this move is that the Leafs traded a second rounder to the Bruins for Khristich.

    Khristich was awarded upwards of $3 million from an arbitrator, but according to reports, the Bruins and Harry Sinden were going to walk away from the offer, thus making him an unrestricted free agent.

    The Leafs (Pat Quinn) decided to jump in on that and acquire the rights to Khristich for a second rounder. The Leafs would sign Khristich and the results you've already read.

    Why did the Leafs offer a second rounder for an eventual free-agent? I guess we'll never know.

11. The Tuukka Rask Trade, Opt to Go with Justin Pogge Instead

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    The Leafs under John Ferguson would trade Tuukka Rask for Andrew Raycroft. Razor, as he was affectionately known to Leafs fans, was a former Calder trophy winning goalie who by all accounts was a decent goalie. However, when the Leafs acquired him, he was coming off a terrible season in which he went 8-19 with a 3.70 GAA.

    Those numbers carried over to the Leafs, where he finished with a Leaf record 37 wins, but with a 3.00 GAA and an .894 save percentage. Pretty pathetic numbers.

    Rask, on the other hand, would go on to take over for Tim Thomas one season and finish with a 1.97 GAA and .931 save percentage. Last season, he lost the starting job to an eventual Vezina Trophy winner, so he's still got plenty of upside.

    Luckily for the Leafs, they managed to draft James Reimer, so this move isn't as bad as it could have been, but still, the move reeks to high heaven.

10. The Owen Nolan Trade and the 2003 NHL Draft

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    Another one of those infamous trades that make the Leafs the old has been group they were known for.

    The Leafs traded Alyn MacCauley, Brad Boyes and a first round pick (Mark Stuart) in return for Nolan who really didn't show anything with the Leafs that he had with the Sharks.

    Boyes went on to be a 40-goal scorer, and the Leafs could have used the first round pick on Ryan Kesler, Mike Richards, Corey Perry, Loui Eriksson, Shea Weber or Patrice Bergeron.

    This deal definitely hurts to look at over and over again. Any one of those players would look awesome in a Leafs jersey.

    To add to the misery, the Leafs' first pick was John Doherty at 57th. The Leafs could've selected David Backes, Jimmy Howard, Clarke MacArthur, Joe Pavelski, Tobias Enstrom, Dustin Byfuglien, Jaroslav Halak and Matt Moulson.

    Yes, obviously this trade was a pretty awful move for the Leafs. The 2003 draft is widely regarded was one of the deepest drafts in NHL history as well. Overall, just a messy, messy situation that year, and one that set the Leafs back many years.

9. Steve Sullivan Released to Waivers, Claimed by the Chicago Blackhawks

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    The Timmins tornado was acquired by the Maple Leafs from the New Jersey Devils, along with Jason Smith and Alyn MacCauley, in return for Doug Gilmour.

    Sullivan would start out his Maple Leaf career slowly; however, in the 1998-99 season, he would finish with a career high 20 goals and 40 points. The next season, Sullivan started out with only one assist in seven games and was unceremoniously released by the club.

    He was claimed off of waivers by the Chicago Blackhawks, where he finished out the season with 22 goals and 42 assists for 64 points in 73 games. All I can say is take that, Leafs management.

    The season afterwards, Sullivan recorded a career high 34 goals and 75 points with the Blackhawks. Oh, it gets worse.

    After the trade, in an 82 game average, Sullivan could've recorded between 65 and 75 points a season if fully healthy.

    With all the issues finding Mats Sundin a scoring winger all these years, they actually had one, and let him get away for nothing at all. Yet another reason why the Leafs haven't seen a Stanley Cup Final in many years.

8. The Leafs Trade Randy Carlyle to Pittsburgh

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    Toronto trades Randy Carlyle and George Ferguson to the Pittsburgh Penguins for Dave Burrows.

    This deal ultimately helped the Penguins nab Mario Lemieux first overall in 1984 and helped guide them to their cup runs of the early 90's.

    Burrows was an absolute stud (sarcasm), scoring 32 points in 151 games. Ferguson, on the other hand, had four-straight 20 goal seasons with the Penguins, and he was the throw-in in the deal.

    Randy Carlyle, though, was the real stud the Leafs lost here. After the trade, Carlyle scored 83 points, 75 points and 56 points in the three seasons following the deal. He won the Norris Trophy in the 1980-81 season, in which he scored 83 points.

    He was then dealt to the Winnipeg Jets, where he enjoyed plenty of success there as well. He was a top two defenceman the Leafs essentially dealt for nothing, and you wonder why the Leafs stunk in the late 70's and 1980's.

    The Penguins used Ferguson ,along with other assets, to acquire pieces to their Cup teams as a result of this team. Ken Wregget, Bob Errey, Rick Tocchet, Kjell Samuellsson and others can have their Pittsburgh roots traced back to this deal.

    The Leafs just keep on giving, don't they?

7. The 1984 Draft and What Could Have Been

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    Al Iafrate had some pretty good seasons as a Maple Leaf. He had a cannon from the point; think Shea.

    Iafrate dealt with numerous injuries throughout his career, including a torn anterior cruciate ligament in his knee, sciatic nerve damage in his back and a ruptured appendix.

    Due to these injuries, Iafrate missed all of the 1994-95 and 1995-96 seasons and played less than 70 NHL games after his 28th birthday, retiring after the 1997-98 season at age 32.

    Iafrate attempted comebacks during the 1998–99 and 2001–02 seasons, although these comebacks didn't get past training camp with the respective teams.

    The what could have been really hurts the brain, though, when you look back on who could have been picked fourth overall in the Mario Lemieux draft.

    Shayne Corson went eighth, Gary Roberts went 12th, Kevin Hatcher went 17th, Patrick Roy went 51st, Brett Hull went 117th, Luc Robitaille went 171st and Gary Suter went 180th.

    Scott Mellanby and Stephane Richer went in the second round. Ray Sheppard went in the third, and Kirk MacLean in the sixth round.

    I really could go on, but in any case, the Leafs really screwed up their drafts in the 80's. Iafrate is a bit of an unknown due to his injuries. If he was healthy, this slide may not be in my slideshow, but since he was injured the majority of his career, he lands here by default.

6. Darryl Sittler Dealt to the Flyers

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    Toronto traded Darryl Sittler to the Philadelphia Flyers for Rich Costello, a second round pick in 1982 (Peter Ihnacak) and future considerations (Ken Strong).

    Obviously looking at that deal, you want to say what the heck! I couldn't blame you. Sittler was likely one of the best, if not the best, Leaf player ever, and still holds the record for points in a game with 10.

    He was 84 points away from recording 1,000 in a Leafs jersey. He would've been the only Leaf to ever do that, but the Leafs took that accolade away from him. Mats Sundin with 994 points is the closest to ever reach 1,000 as a Leaf.

    Costello and Strong would play around 27 games between the two of them in the NHL, while Ihnacak would play 337 games and score 201 points as a Leaf before returning to Europe.

    Sittler would go on to record 178 points in 191 games as a Flyer, and the organization was forever in debt for getting Sittler for essentially a bag of potato chips and a couple of scratch tickets. Another deal that just makes me shake my head.

5. The Leafs Trade Bernie Parent

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    Toronto trades Bernie Parent and a second round pick in 1973 (Larry Goodenough) to the Philadelphia Flyers for a first round pick in 1973 (Bob Neely) and future considerations (Doug Favell).

    The Leafs were never a team that took pride in drafting players, and they obviously didn't do their homework after making this deal.

    Parent went on to become the Flyers best goalie in the franchise's history. Funny fact, the Flyers have not found a goalie since Parent to lead them for years. Hopefully they found one now in Ilya Bryzgalov.

    The Leafs had a young goalie on their hands, but he decided to split and head to the WHA, which essentially made him persona non grata with Leafs management and ownership.

    Parent requested a trade to Philadelphia after that, and in his first two seasons with the Flyers, Parent won two Stanley Cups, two Conn Smythe trophies and two Vezina trophies. He was the best goalie in the league, in other words.

    He was masterful in posting a record of 177-60-57 in 298 games over six seasons with the Flyers.

    Neely was a decent defenseman for about four years, but after that, he disappeared, and as for Favell, he had a decent year with the Leafs in his first season, but after that, he just got worse before eventually being dealt to the Colorado Rockies.

    The Leafs, however, had two more first rounders that year and drafted Lanny MacDonald and Ian Turnbull with their two other picks. The deal sucks, but at least the Leafs totally didn't screw up at the draft.

4. The Hiring of John Ferguson Jr.

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    John Ferguson, Jr. may be one of the worst GM's ever in Leafs history. He is known around the NHL circles as the No-Trade Clause Man; he seemed to give them out like candy during his tenure. However, I'll give it to him for his drafting, which wasn't that bad.

    Some of his moves just reeked which included the Rask deal (listed earlier), drafting Jiri Tlusty and many others.

    Here are a sample of his moves.

    • One-year deal given to Jason Allison
    • Traded Ken Klee for Alex Suglobov
    • Bryan McCabe $5.75 Million NMC
    • Tukka Rask for Andrew Raycroft Deal
    • Brendan Bell and second for Yanic Perrault
    • Fourth round pick for Luke Richardson
    • Eric Lindros one year Deal
    • Hal Gill $2.00 Million per three years
    • Alexander Khavanov signing
    • Ed Belfour Deal in 2004 (led to his buy out)
    • Mikael Tellqvist for Tyson Nash and a fourth
    • Fired Pat Quinn, Hired Paul Maurice
    • Jarko Immonen and first round pick for Brian Leetch (only one season)
    • Darcy Tucker four-year, $12 million deal
    • Joe Nieuwendyk and Gary Roberts let go, signed in Florida
    • Opted not to bring back Doug Gilmour after he injured his knee in Calgary
    •  Signed Calle Johansson
    • Did not re-sign Michael Peca
    • Ron Francis for fourth round pick
    • Pavel Kubina $5 million contract with a no-trade clause
    • Jason Blake five-year contract

    Draft Picks Traded

    • First round 2004
    • First round 2005 (Tuukka Rask)
    • First round 2007
    • Second round 2005
    • Second round 2007
    • Second round 2008
    • Fourth round 2005
    • Fourth round 2006
    • Fourth round 2009
    • Fifth round 2006

    I'll spare the heartache in listing everyone who was drafted, or at least could have been drafted with these picks.

3. The 1988 and the 1989 Gord Stellick Draft

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    In these two drafts, you can arguably say the Leafs massively disappointed everyone with their picks.

    In 1988, they had the sixth overall selection and opted to take Scott Pearson.

    Jeremy Roenick, Rod Brind'Amour and Teemu Selanne were taken eighth, ninth and 10th overall shortly after. Martin Gelinas was taken right after Pearson. These four players each played a minimum of 1,259 games in the NHL and amassed over 4,400 points between the four of them.

    Later on in the '88 draft, Alexander Mogilny was also drafted.

    Tony Amonte, Marl Recchi and Rob Blake went in the fourth round, along with Keith Carney and Joe Juneau, who both had good, long careers in the NHL.

    Dmitri Khristich and Bret Hedican were taken very deep in the draft, and I won't harp on them for not taking these guys.

    In 1989, the Leafs used their third overall selection to take Scott Thornton. Stu Barnes and Bill Guerin went directly after Thornton, and Bobby Holik, Mike Sillinger and Olaf Kolzig also went in the first round.

    Adam Foote was the first pick in the second round, and Nicklas Lidstrom went in the third round; yes, the third round.

    Sergei Fedorov went in the fourth round, Pavel Bure in the sixth round and Donald Audette in the ninth round.

    Thornton played 941 games in the NHL; however, only scored a measly 240 points.

    Pearson was even worse, playing in only 292 games and scoring a mere 98 points.

    These were the down years in Leaf-land, and you can understand why.

2. Leafs Trade Their First and Second Round Picks in 1991

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    Here are the two trades.

    Leafs traded their third overall selection to the New Jersey Devils in return for Tom Kurvers. The Devils used that pick to select captain Scott Niedermayer, and the rest is history.

    The Quebec Nordiques traded Michel Petit, Lucien DeBlois and Aaron Broten to the Maple Leafs for Scott Pearson, the 1991 second round pick (No. 25, Eric Lavigne) and the 1992 second round pick (No. 29, Tuomas Gronman) on November 17, 1990.

    I mean, the second rounder never amounted to much, but the Leafs still could have selected a different players.

    Players not taken from the 1991 draft include Peter Forsberg, Brian Rolston, Alexei Kovalev, Markus Naslund, Glen Murray and Martin Rucinsky. All went in the first round after the third selection.

    After the first round, players taken include Ray Whitney, Zigmund Palffy, Sandis Ozolinsh, Chris Osgood, Alexei Zhitnik, Mariusz Czerkawski, Dmitry Yuskevich and Dmitri Mironov.

    Again, I love to stress this, but you have to build through the draft to be successful, and in the Leafs down years, you can tell the direct reason why they sucked. They needed to draft better, plain and simple.

1. Conn Smythe Selling the Leafs to a Group Which Included Harold Ballard

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    This is easily the biggest mistake that happened in Leafs history, and that was giving Harold Ballard full control of the team.

    Rumors had it, a drunken Stafford Smythe, co-owner of the Leafs at the time, was coerced into selling his share of the team to Ballard by Ballard himself. Ballard was born a crook.

    Ballard was all about making money and never about winning and making his players and employees happy. He has went down as likely the most hated NHL owner in league history.

    When Smythe eventually died in 1971, Ballard assumed total control of the squad, and really, ever since he took over, the Leafs just got worse and worse by the year.

    Ballard would run countless Leafs out of town, mainly some of the best to ever lace them up in a Leafs jersey. Darryl Sittler was dealt for practically nothing just to get his face out of the Gardens. 

    Lanny MacDonald was given away as well in a trade with the Colorado Rockies.

    Dave Keon's relationship with Ballard was tumultuous at best, and when his contract expired in 1975, the 15-year Maple Leaf was set free to sign in the WHA. Keon would receive an offer from the up and coming Islanders team; however, Ballard still held the rights to Keon and blocked the deal. Keon was allowed to finish his career out in Hartford. Keon hasn't forgiven the Leafs organization since.

    Ballard had a bad attitude towards player salaries and wanted to control them better; however, this had him at odds with the NHLPA. One member of the NHLPA at the time was Darryl Sittler, who eventually fell out of favor with Ballard, and yes, was sent packing as well by the enigmatic owner.

    A full description of Ballard's work can be found here

    Needless to say, he hurt a lot of people, and with his micromanaging of the Leafs from the time he was bought the club, to the day he died in 1990, the Leafs rarely made any playoff appearances and were a disgrace in the NHL after Sittler was dealt out of town.

    Easily the worst thing to happen to this organization in all of its existence.