The 25 Worst Trades in Toronto Maple Leafs History: #1 to 5

Trades #1-5 of the 25 Worst Trades in the modern history of the Toronto Maple Leafs.

Intro - Leafs Logo Simple

Links to the other individual articles in this series: Intro, #21-25, #16-20, #11-15, #6-10

And here we are, the five worst trades in the modern history of the Toronto Maple Leafs.  What you’ve read up until this point is but an appetizer to the main course of self-loathing, depression and frustration that you are about to digest.  And if you haven’t read the previous trades, shame on you!  Before we begin, let us revisit #6-25 on the list.

  • #25: Ken Wregget to the Philadelphia Flyers for a 1989 1st Round Pick (Rob Pearson) and a 1989 1st Round Pick (Steve Bancroft) (March 1989)
  • #24: Alyn McCauley, Brad Boyes and a 2003 1st Round Pick (Boston selected Mark Stuart) to San Jose Sharks for Owen Nolan (March 2003)
  • #23: Dallas Stars receive Peter Zezel and Grant Marshall (August 1994) as compensation for Toronto signing Dallas RFA Mike Craig (July 1994)
  • #22: Laurie Boschman to the Edmonton Oilers for Walt Poddubny and Phil Drouillars (March 1982)
  • #21: A 2007 1st Round Pick (St. Louis selected Lars Eller), a 2007 2nd Round Pick (St. Louis selected Aaron Palushaj) and a 2009 4th Round Pick (Nashville selected Craig Smith) to the San Jose Sharks for Vesa Toskala and Mark Bell (June 2007)
  • #20: Fredrick Modin to the Tampa Bay Lightning for Cory Cross and a 2001 7th Round Pick (Ivan Kolozvary) (October 1999)
  • #19: Jim Pappin to the Chicago Blackhawks for Pierre Pilote (May 1968)
  • #18: Frank Mahovlich, Garry Unger, Pete Stemkowski and the rights to Carl Brewer to Detroit for Norm Ullman, Paul Henderson, Floyd Smith and Doug Barrie (March 1968)
  • #17: Larry Murphy to the Detroit Red Wings for Future Considerations (Cash) (March 1997)
  • #16: “Three G’s Salary Dump” (June 1996)
    • #16A: Todd Gill to the San Jose Sharks for Jamie Baker and a 1996 5th Round Pick (Peter Cava)
    • #16B: Dave Gagner to the Calgary Flames for a 1996 3rd Round Pick (Mike Lankshear)
    • #16C: Mike Gartner to the Phoenix Coyotes for a 1996 4th Round Pick (Vladimir Antipov)
  • #15: Tuukka Rask to the Boston Bruins for Andrew Raycroft (June 2006)
  • #14: Kenny Jonsson, Sean Haggerty, Darby Hendrickson and a 1997 1st Round Pick (Roberto Luongo) to the New York Islanders for Wendel Clark, Mathieu Schneider and D.J. Smith (March 1996)
  • #13: Toronto’s Craig Muni becomes an Unrestricted Free Agent, signs with the Edmonton Oilers (August 1986)
  • #12: Boston Bruins claim Gerry Cheevers from Toronto in the NHL Intra-League Draft (June 1965)
  • #11: Lanny McDonald and Joel Quenville to the Colorado Rockies for Pat Hickey and Wilf Paiement (December 1979)
  • #10: The Tampa Bay Lightning claim Brian Bradley from Toronto in the 1992 Expansion Draft (June 1992)
  • #9: Jason Smith to the Edmonton Oilers for a 2000 2nd Round Pick (Kris Vernarsky) and a 1999 4th Round Pick (Jonathon Zion) (March 1999)
  • #8: Darryl Sittler to the Philadelphia Flyers for Rich Costello, a 1982 2nd Round Pick (Peter Ihnacak) and Future Considerations (Ken Strong) (January 1982)
  • #7: Doug Jarvis to the Montreal Canadiens for Greg Hubick (June 1975)
  • #6: Russ Courtnall to the Montreal Canadiens for Jon Kordic and a 6th Round Pick in 1989 (Mike Doers) (November 1988)

And now… on with the not-so-grand finale!

#5A: Toronto trades a 2nd Round Pick in 2000 (Ivan Huml) to the Washington Capitals for Dmitri Khristich (October 20th, 1999)
#5B: Toronto allows the Chicago Blackhawks to claim Steve Sullivan via waivers (October 23rd, 1999)

On the surface, the first trade looks harmless.  Boston didn’t do much with the draft pick, and Khristich’s numbers in year one (30 points in 53 games) suggest a decent hockey player.  But don’t let that fool you, he was AWFUL.  His second season (9 points in 27 games) was so bad the Leafs dealt him back to Washington for a 3rd round pick in 2001 (which turned into Brendan Bell… who then, in keeping with Leafs’ tradition, turned into 17 games and 5 points from Yanic Perreault).  Khristich is the closest thing to a Maple Leaf player that I hated besides Mike Craig.  Now you may be wondering why a moderate gamble of a second-round pick for a 6-time 27+ goal scorer (pre-Toronto) ranks so highly on this list.  Well, there are two very valid reasons.  First, there were rumblings (which I believe) that Boston walked away from Khristich’s arbitration settlement, which would have made him an unrestricted free agent.  But instead of simply SIGNING him, Leafs GM Pat Quinn traded a 2nd round pick to Boston for Khristich’s rights to “keep the peace”, after which point Quinn signed Khristich.

The second reason why this trade ranks so highly is because in order to make space on the roster for Khristich, Quinn put a young, small forward on waivers.  Quinn preferred veterans, and big tough players.  Sensing an opportunity, the Chicago Blackhawks plucked Steve Sullivan off waivers.  After leaving Toronto, Sullivan posted seven consecutive seasons where he scored 22+ goals and recorded 60+ points.  If those seven seasons had been in a Toronto uniform, five of them would have placed him SECOND in Leafs scoring, and the other two would still have been in the top five.  Yes, I am saying that in those seven post-Sullivan seasons, five of those seasons lacked a Leafs player scoring 60 or more points who wasn’t named Mats.  Sullivan scored 118 goals and 303 points in 370 games for Chicago, raising his stock to the point where the Nashville Predators acquired him at the 2004 trade deadline.  The cost was a pair of 2nd Round draft picks.  He then scored 158 points in 150 games for the Predators before sitting out the 2007-08 season due to injury.  And after coming back, he posted a pair of 17-goal, ~50-point seasons (’09-10 and ’11-12).  As of the start of the 2012-13 NHL season, Sullivan had 283 goals and 730 points in 969 career games.  Just a terrible, TERRIBLE trade, one that confirmed the Leafs squandered all the resources they received from the Doug Gilmour trade.  Depressingly, each of Sullivan, Jason Smith and Alyn McCauley can be found on this list.  Imagine how good that trade would look if those three players had spent the bulk of their careers in Maple Leaf uniforms.

#4: Toronto trades Randy Carlyle and George Ferguson to the Pittsburgh Penguins for Dave Burrows (June 14th, 1978)
Leaf fans recognize Randy Carlyle as their head coach, but many would be fairly surprised at finding out he was a former Maple Leafs player.  But those of you reading this list will likely NOT be shocked at the idea that trading him early in his career for veteran help worked out badly for Toronto.  The Leafs wanted a steady hand on their blueline, and so they approached the Pittsburgh Penguins.  Though hardly a powerhouse at the time (their struggles in the late 70s and early 80s eventually led to their getting Mario Lemieux first overall in the 1984 Entry Draft), they did have a player who fit the bill: Dave Burrows.  Unfortunately, Burrows did absolutely nothing for Toronto.  In two seasons and change, he recorded 32 points in 151 games, and played in just nine playoff games during that span.  He was then traded back to Pittsburgh in a deal that did nothing for either team.

The Penguins, meanwhile, made out like bandits.  George Ferguson recorded four straight 20-goal seasons, and was even a strong performer in Pittsburgh’s first-round playoff exits (15 points in 22 games).  But Randy Carlyle was the true gem of this deal.  He played 397 games as a Penguin, recording 323 points.  As a DEFENSEMAN.  In fact, he won the Norris trophy as the NHL’s best defenseman, recording 83 points in 1980-81.  He then went on to play another 564 games for the Winnipeg Jets, recording another 306 points.  Despite playing on some truly terrible teams that rarely made the playoffs, he still managed to contribute 31 points in 53 playoff games after leaving Toronto.  Again, as a defenseman.

But wait, it gets worse (as if we needed something worse giving up a consistent 20-goal man and a 1,000-game defenseman).  The Penguins further benefitted from this trade through BRILLIANT asset management.  Ferguson and the 1st overall pick in 1983 were traded to Minnesota for the North Stars’ first round pick and two players.  The players didn’t amount to much, but Pittsburgh selected Bob Errey, who spent a decade in a Penguins jersey, winning two Stanley Cups.  Meanwhile, Carlyle was traded to the Jets for a 1st round pick in 1984 and Future Considerations.  The draft pick ended up being Doug Bodger, while the FC became Moe Mantha.  Mantha recorded 168 points in 232 games for the Penguins, before becoming part of the Paul Coffey trade.  Coffey (after helping Pittsburgh win the 1991 Cup) in turn helped net the Penguins Kjell Samuelsson, Rick Tocchet and Ken Wregget from Philadelphia (which led to the 1992 Cup).  As for Doug Bodger, he contributed 167 points in 299 games.  Pittsburgh then traded him to the Buffalo Sabres for goaltender Tom Barrasso, an integral part of their back-to-back championship teams.  So the Penguins turned Randy Carlyle into various components of one of the few back-to-back Cup champions of the last 20 years, AND got another decade of service from a quality player for George Ferguson.  *sigh*  It’s very depressing writing about a team that knows how to continually turn over their high-value assets into new, long-term assets.  If only Craig Patrick had been Leafs’ GM… he would have moved Tucker, McCabe and possibly Sundin in 2005, rather than signing them to no-movement clauses after yet another 1st-round exit.

#3: Toronto trades Rick Kehoe to the Pittsburgh Penguins for Blaine Stoughton and a 1st Round Pick in 1977 (Trevor Johansen) (September 13th, 1974)
Rick Kehoe was a quality hockey with the Maple Leafs, scoring 33 goals and 75 points in his first full year with the team.  But his ice time decreased when Lanny McDonald and Inge Hammarstrom joined the team, and he wanted out.  Pittsburgh game along with a tempting offer of young talent, and the Leafs jumped at the deal.  Kehoe was an absolute beast for some pretty terrible Penguins teams.  Between ’74-75 and ’82-83, he averaged 33 goals and 65 points.  He never scored fewer than 29 goals or 50 points, and had a career-best 55 goals and 88 points in the 1980-81 season (the one where Carlyle won his Norris).  He suffered a neck injury in the ’83-84 season, when he was still scoring at close to a point-per-game, and he was forced to retire early in the ’84-85 season.  Over a twelve-year period, he never scored fewer than 18 goals or 40 points.

Johansen was a bust for the Leafs; in parts of three seasons, he contributed a total of 57 points and 282 penalty minutes over 286 games.  He ended up being shipped to Colorado for Paul Gardner, who then went to Pittsburgh with Dave Burrows (from trade #4) for Kim Davis and Paul Marshall.  Combined, Gardner, Davis and Marshall played just 56 games in Toronto uniforms.

Appearances to the contrary, this is NOT Jesus or one of the Bee Gees.

Now the good news is Blaine Stoughton turned into a tremendous NHL player.  But the bad news is, of course, it wasn’t in Toronto.  Stoughton played parts of two seasons for the Leafs.  His first showed promise: 23 goals and 37 points.  But he opted to leave Toronto for the WHA, just as Bernie Parent and many other Leafs prospects did.  Apparently Harold Ballard had a strict no-matching policy when players approached management with WHA offers, which cost the Leafs a significant portion of their depth and contributed significantly to their downward slide that bottomed out in the 1980s.  Stoughton was a member of the New England (later Hartford) Whalers when the WHA folded, and Toronto allowed Hartford to grab him in the 1979 Expansion Draft.  Stoughton celebrated his return to the NHL with four straight 43+ goal, 73+ point seasons, including a fantastic 56-goal, 100-point performance in ’79-80.  He ended up scoring 224 goals and 384 points in 371 NHL games after leaving the Maple Leafs.  It’s amazing that even when they are a part of a trade involving two youngsters who each became 50-goal scorers, the Leafs STILL find a way NOT to benefit.  I don’t care if that sentence is grammatically correct or not, because it is emotionally apt.  DAMN YOU BALLARD!!!

#2: Toronto trades Bernie Parent and a 2nd Round Pick in 1973 (Larry Goodenough) to the Philadelphia Flyers for a 1st Round Pick in 1973 (Bob Neely) and Future Considerations (Doug Favell) (May 15th, 1973)
There are bad trades… and then there are truly wretched trades.  Cam Neely from Vancouver to Boston.  Ron Francis from Hartford to Pittsburgh.  Phil Esposito from Chicago to Boston.  I could go on, but suffice it to say that this Leafs trade definitely falls into the second category.  Toronto had a young goaltender on their roster who left the club to play in the World Hockey Association, which instantly made him an outcast in the eyes of Leafs management and ownership.  Having played previously in Philadelphia (both with the NHL’s Flyers and the WHA’s Blazers), Parent requested a trade to Philadelphia.  His request was granted, and all he did in his first two seasons back with the Flyers was win two Stanley Cups, two Conn Smythe trophies as the MVP of the playoffs, and two Vezina trophies for helping the Flyers post the lowest goals-against total in the league.  So he was the best goaltender in the league, and the most valuable player on the back-to-back Stanley Cup champions.  He was incredible during his second tour with the Flyers, posting a record of 177-60-57 in 298 games over six seasons.  And he also had a record of 33-22 in the playoffs.  Larry Goodenough was merely Decentenough (sorry), scoring 71 points in 129 games for Philadelphia, but he was a hero in their failed attempt to three-peat in 1976, scoring 14 points in 16 games.  He was eventually traded to Vancouver.

Meanwhile, in Toronto. Doug Favell was a complete bust.  He was decent for the Leafs in his first season, just plain AWFUL in his second, and gone just three games into his third season.  He was sold to the goaltending hell that was the Colorado Rockies.  For cash.  Now the trade with the Flyers DID give the Leafs three first round picks in the 1973 Entry Draft.  The Leafs were STELLAR with the other, selecting Lanny McDonald and Ian Turnbull.  But sadly, Bob Neely was who they chose with the pick acquired from the Flyers.  Neely posted decent-but-not-great numbers as a Leafs defenseman: he contributed 89 points and 264 penalty minutes in four-plus seasons, as well as 12 points in 26 playoff games.  But he played just 22 games after leaving Toronto.  And he too was shipped to the Colorado Rockies for cash.  That’s right; all we had left to show in for giving up on Bernie Parent in net was CASH.  Essentially, the Leafs received just over four seasons (three of them decent) from a mid-level defenseman and two seasons (one of them somewhat good) from a back-up goaltender, and cash.  In exchange for a hall-of-fame keeper who was possibly the best money goaltender in the 1970s.  BRILLAINT!!!  And in case it sounds like 20-20 hindsight is making me bitter, Parent posted better numbers in his two seasons in Toronto than Favell did in his entire career.  Never mind his stats from his first tour with the Flyers when they joined the NHL in 1967.  The man was clearly a talented goalie who deserved a roster spot in Toronto.

#1: Toronto trades a 1st Round Pick in 1991 (Scott Niedermayer) to the New Jersey Devils for Tom Kurvers (October 16th, 1989)
And here we are… the most infamous trade in Toronto Maple Leafs history (modern or otherwise).  Now earlier I stated that I ignore the draft choices made by other teams, because there is no guarantee that Toronto would have chosen that player (i.e. the Islanders choosing Roberto Luongo with the draft pick from the Leafs).  However, in this case I can argue that Toronto would almost assuredly have chosen a player of consequence.  Of the 22 players chosen in the first round, 17 played in at least 575 NHL games.  Of the other five, two of them still managed to play over 100 games (and one of them, Alex Stojanov, was traded by Vancouver for Markus Naslund).  That’s a 77% chance that Toronto would have had received 575+ games from a first rounder, and an 86% chance of receiving 100+ games (which is more than they got out of Tom Kurvers).  And the cream of the 1991 crop would be considered top-flight players in almost any NHL era.

Right off the bat, I will state this; Tom Kurvers by himself was NOT a bad acquisition.  The year before the Leafs acquired him, they went 28-46-6 (’88-89 season) and missed the playoffs.  With him in 1989-90, they went 38-38-4 and scored 78 more goals than the year before.  Kurvers recorded 52 points and a not-too-bad -8 rating in 70 games, along with 3 assists in 5 playoff games.  Quite decent, and demonstrating that Kurvers was worth trading for… just not at the cost of a first round pick.  But then the next season (’90-91), with just 3 assists in 19 games, the Leafs dealt him to Vancouver.  The Leafs would finish the season with a record of 23-46-11, missing the playoffs by 11 points.  In exchange for Kurvers, the Leafs received Brian Bradley.  Yes, that would be the very same Brian Bradley that the Leafs held onto for one-and-a-half seasons, before letting him go in the ’92 Expansion Draft (for nothing) to the Tampa Bay Lightning.  So in total, dealing their 1991 1st Round Draft Pick resulted in 55 points in 89 games from Tom Kurvers, and 42 points in 85 games from Brian Bradley.  To summarize, dealing the first rounder gave Toronto 97 points in 174 games.  And the WORST of it all was that Bradley left Toronto on June 18th, 1992, four days before the entry draft.  The draft hadn’t even HAPPENED yet, and the Leafs had already lost the trade.  Of the 17 players chosen in the first round of the 1991 Entry Draft with at least 575 NHL games played in their careers, Scott Lachance (a defensive defenseman) had the lowest point total (143 in 819 games).  Hell, Pat Peake only played 134 games, and HE still managed 69 points.  And so by this alone, the Leafs screwed up enough for this trade to end up in the top ten trades that make it possible for jerseys like these to exist:

And now comes the clincher, the reason why this trade is #1 with a bullet.  The Leafs were bad in 1990-91… so bad in fact that they were on pace to finish last in the NHL behind the Quebec Nordiques.  Toronto was feeling the sting of Kurvers not working out as expected, and they were terrified at how bad they would look if the cost of Kurvers was the first overall pick.  So the Leafs traded prospect Scott Pearson and a pair of 2nd Round picks to Quebec, which the Nordiques used to select Tuomas Gronman and Eric Lavigne.  The draft picks were busts: Gronman played 38 NHL games (none for Quebec), while Lavigne played exactly one NHL game for the L.A. Kings).  Pearson never really amounted to much in Quebec, and the Nordiques traded him to Edmonton for Martin Gelinas.  Unfortunately, the Nordiques let Gelinas go on waivers, and he went on to score the bulk of his 309 career goals for Vancouver, Carolina and Calgary.  In return for this package of failed potential, Toronto received Lucien DeBlois, Aaron Broten and Michel Petit.  DeBlois didn’t do much, but the Leafs did flip him to Winnipeg for Mark Osborne’s second tour of duty in Toronto, and he was a part of their deep playoff runs in ’93 and ’94.  Petit had decent offensive numbers for Toronto, and was a part of the blockbuster 10-player deal with the Flames that brought Doug Gilmour to Toronto.  Broten somehow managed to post a +12 rating in 27 games for the Leafs (but just 10 points), and was allowed to walk as a free agent.  So on the surface, this trade looks like a big win for Toronto.

But here’s the thing: “winning” this trade was not even remotely the priority for Quebec.  They sent three regulars players to Toronto.  Now they weren’t exactly all-stars, but they were regular players on a terrible team.  And their removal accomplished one key thing: it necessitated their replacement with younger, less talented players.  Therefore, it made Quebec worse.  The Leafs even picked up another Nordique (Claude Loiselle) near the trade deadline just in case.  Now why you ask would the Leafs trade Pearson (their 1988 1st Round choice) and a pair of second round picks for three players from the worst team in the league?  Because by making Quebec slightly worse and Toronto slightly better, it decreased the chances of Toronto finishing last overall in the league.  And it worked: in the end, Quebec’s 46 points put them 21st (out of the NHL’s then 21 teams), behind Toronto’s 57 points (which ranked 20th, three back of the New York Islanders).  So what could almost sound like a noble goal (improving your team at the cost of an opponent’s immediate success) clearly wasn’t done with noble intentions.  Because the SOLE reason the Leafs made this deal with Quebec was to avoid finishing dead-last, which would have given the first overall pick to New Jersey.  Which in turn would have resulted in New Jersey turning Tom Kurvers… into teenaged phenom Eric Lindros.

#01 Eric Lindros NHL Jersey#01 Eric Lindros Draft

Before with full historical perspective, you might be tempted to downplay my ominous tone. But keep in mind that in 1991, Eric Lindros was THE next great player.  Not an Alexander Daigle “he might be the next one” falsely-hyped saviour.  We’re talking a Sidney Crosby “he WILL be the next one”, a guaranteed marketing goldmine and game-changer for any franchise.  Lindros scored 71 goals and 149 points in 57 games during his last juniour year.  He was so good that he was picked as an 18-year-old to play on the 1991 Canada Cup team with Gretzky, Messier, Coffey, Robitalle and more.  A team so deep that Steve f’n YZERMAN was cut from the squad.  And even though Lindros’ career can arguably be classified as disappointing, he still recorded 372 goals and 865 points in 760 games.  Four 40+ goal seasons, a positive +/- rating in his first eight seasons, and pretty much a lock for 30-50 assists a year.  He also almost brought the 1997 Cup to Philadelphia single-handedly, scoring 12 goals and 26 points in 19 games.

Fortunately for the Leafs though, their Quebec raids paid off and the Nordiques finished last in the league, giving Quebec the first overall draft pick.  Quebec chose Lindros and, after he refused to play there and held out for a year, Quebec traded him to the Flyers for a package (including Peter Forsberg and Ron Hextall) that transformed the Nordiques from laughing stock to (as the Colorado Avalanche) Stanley Cup champions.  And if the rumour mill is to be believed, Toronto offered a package including Doug Gilmour, Wendel Clark, Dave Ellett and possibly Felix Potvin.  When all they would have had to do was NOT acquire Tom Kurvers three years prior.

But getting back to original Kurvers trade.  Lindros would have conceivably been the only true superstar that this generation of Maple Leafs fans have ever seen.  No offense to Gilmour and Sundin, but Gilmour’s run at the top was too short, and Sundin’s lack of individual accolades (and playoff success) held him back from Superstar status.  As it was, the Leafs breathed a sigh of relief when Quebec’s poor finish and the creation of the San Jose Sharks meant that New Jersey would pick third overall.

But the Devils chose very, VERY well; they picked Scott Niedermayer.  Niedermayer is one of the true great defenseman of this (or possibly any) generation.  He scored 476 points in 892 games and posted a +172 ratings in 12+ seasons with New Jersey, winning Stanley Cups in 1995, 2000 and 2003 (and very nearly another one in 2001).  He then signed with the Anaheim Ducks as a free agent, where he added another 264 points in 371 games, as well as fourth Stanley Cup ring in 2007.  In addition to his incredible 740 career regular-season points, he also recorded 25 goals and 98 points in 202 playoff games.  Niedermayer’s success extended well beyond the NHL level: he also won a Memorial Cup (the championship for Canadian hockey at the juniour level), and gold medals at the World Juniour Championship, the World Championship, the World Cup (of hockey) and the Winter Olympics.  The man was a winner on every single stage that he played.  The truly sad part… picking first or third (assuming they were smart enough to pick Niedermayer) would have given the Leafs a TRUE franchise player who would have spent a decade in their line-up.  Any number of players from the 1991 draft could have boosted the club’s fortunes longer term than Kurvers/Bradley.  You want scoring?  Peter Forsberg went 6th overall, and other options from the first round included Brian Rolston, Alexei Kovalev, Markus Naslund, Glen Murray and Martin Rucinsky.  Defense?  Scott Lachance, Aaron Ward, Richard Matvichuk and Philippe Boucher all played 700+ quality games.  Even a “bust” like Pat Falloon still scored 322 points.

This was the trade that truly bottomed out the franchise at the end of 1980s.  Think of a 19-year-old Eric Lindros or Scott Niedermayer playing on the 1992-93 Leafs alongside Gilmour, Andreychuk, Clark and Potvin.  It would have completely changed the dynamic of the team.  And Sundin would have had some help in keeping the team from being awful in the mid-to-late 1990s.  Lindros or Niedermayer might have been enough to turn one of those Conference Finals runs into a Stanley Cup Final appearance… or heaven forbid, a championship.  And worst-case scenario, Lindros might even have helped out the Blue Jays.

But that’s both the beauty and the pain of professional sports… the what-if’s, the could-have-been’s, and the wish-they-weren’ts.  Then again, that’s also the reason why lists like this are possible.  Every team has their share of glorious moments and tragic instances, and it’s unfortunate that Toronto has had more than their share.  I hope you’ve enjoyed reading my selections for the Top 25 Worst Trades in Toronto Maple Leafs History as much as I enjoyed writing them.  And in an attempt to stave off dark thoughts and pending depression, I’ve already begun working on the best trades in Leafs history.  While I’m sure we haven’t seen the last of bad Leaf trades, we Leafs fans still cling to the hope that another Gilmour-type trade will bring the franchise back to life and finally get us a Stanley Cup parade of our own to cheer.  Go Leafs Go.


14 thoughts on “The 25 Worst Trades in Toronto Maple Leafs History: #1 to 5

  1. #2 trade, on LeafsTV way back they spoke about this trade and it was one the Leafs didn’t want to make but Bernie no longer wanted to play in Toronto (I think the reason was money).
    Hard to argue the Kurvers trade for a #1 when you are a team rebuilding. Always hated the Pappin/Pilote trade. For some reason Punch never liked Papin. Pilote was close to retiring and Pappin had lots of good hockey left. Another is trading Tim Horton to the Rangers for Denis Dupere. I know he was getting older, but his play never fell off. The Leafs D was young and inexperienced and by 70-71 the Leafs had turned it around and certainly could have used him in the playoffs that season. I never saw Horton play a bad game.

    • Regarding Parent, I believe you’re right. But the entire issue could have been avoided if they had matched the WHA offer in the first place. He played for the Philadelphia Blazers and, if I recall correctly, enjoyed it so much that he wanted to play for the Flyers when he returned to the NHL. If they cut that off and keep Parent from going to the WHA, he never becomes enamored with Philadelphia, and never demands to be traded to the Flyers.

      The Kurvers trade was brutal, plain and simple. They were guilty of what many Leafs’ GMs since have done: tried to accelerate the rebuild. They had an interesting core, and they were developing nicely: they should have continued to build rather than sacrifice the future. The Quebec trade would never have happened if the Leafs still held the rights to their pick, so it is entirely likely they would have gotten Niedermayer or possibly Lindros. Throw those two onto the Leafs’ Gilmour-led roster, and that adds an interesting dynamic. With Lindros, they would never have had to make the John Cullen trade, and they would have had a fantastic #1 and #1A lineup at centre with Gilmour and Lindros. Lindros, Anderson and Clark would make for a very interesting, and Anderson could have helped guide Lindros along in his formative years. Or going the other way, a young Niedermayer playing alongside Dave Ellett on the powerplay and feeding pucks to Gilmour and Andreychuk makes the Leafs a more dynamic breakout team. Instead the Leafs got some decent hockey from Tom Kurvers, and barely adequate offence from a pre-Tampa Bay Lightning-breakout Brian Bradley. Ugh.

      The Papin trade baffles me… but it is so similar to other moves (Nolan, Leetch, Khristich/Sullivan) that it almost becomes depressingly predictable.

      I didn’t know review the Tim Horton deal when I made the list. Looking at it briefly now, I don’t think I could have put it on the list: Dupere played in parts of four seasons for Toronto, topping out at 36 points in 61 games in ’72-73. Horton never scored more than 20 points in a season, and only once played more than 70 games over the next four seasons. He did have a stellar +28 rating for the Rangers in ’70-71, but was definitely over the hill. It’s a shame they didn’t allow him to retire as as Leaf, but they did have the wherewithal to at least try and trade a clearly-declining asset for a prospect. Something I wish they had had the guts to do more in the past.

      Excellent feedback, thank you for sharing!

  2. Great summary….well laid out, especially in the explanation of the top 5. One question for you. Knowing what we know now about Rask would you grade that as an even worse deal? From my side, it could turn into a top 5 worst deal. Thoughts?

    • I feel fairly comfortable in saying the Rask trade would DEFINITELY be in my Top 10 now, and RIGHT on the cusp of the Top 5. It is definitely more damaging to the franchise than the Courtnall deal. Steve Sullivan had a fantastic career after leaving Toronto, and he was quite good for a very long time. Rask has been excellent, but has only been the #1 netminder in Boston for a short period. For now I would slot this trade at #6, but could easily see it creeping up into the #4 or even #3 slot over the next 2-3 seasons.

      I am also quite happy that, with the benefit of hindsight, I was right about the Kessel deal. Boston couldn’t handle Seguin, and the Leafs appear confident that Kessel is their star player (as evidenced by the mammoth contract he signed recently). They still overpaid, but at least people aren’t as focused on what was given up for him as they were previously. And overpaying for a good (and occasionally great) player doesn’t make a deal a loss.

  3. The Parent trade looked ok when it was first made because Favell was highly regarded. Ballard was just released from jail and with majority control was beginning to exhibit the behaviour that destroyed the franchise.

    It is what happened in the background that was the real travesty.

    After Parent’s value was proven in the 1971 playoffs, he and the club agreed to a three year deal in the $30-40K range. At that point it was a handshake deal. As the WHA was shaping up in December, Parent’s agent advised him not to formally sign. The Leafs – thinking the WHA wouldn’t happen and with complete faith in the reserve clause – never pushed to sign him. So he played 1971-72 and was able to sign with Miami late that season. Ballard didn’t want to match the offer and by all accounts Parent parted on good terms. Ballard, like many NHL execs, never thought the league would go and all the players would return…when that didn’t happen and the Leafs stunk, Ballard’s attitudes toward the WHA and the jumping players hardened. Parent ended up with a multi-year deal with the Philadelphia Blazers in the $125K per season range.

    By the end of the 1972-73 season, the Blazers were drowning in red ink and without the money he was guaranteed, Bernie left the club in the playoffs under bad terms. Over the summer of 1973, he had two options – sign with another WHA team or go back to the Leafs. He didn’t like the empty seats and instability of the new league. So his agent approached the Leafs. Ballard – by then running roughshod over everybody – actually offered LESS than the handshake deal from the fall of 1971! Given Parent’s solid play as a Leaf, there was no way Parent was returning to the Leafs after that. He demanded a trade and Leaf GM Jim Gregory – in an attempt to salvage something – made the deal. On the surface the deal looked ok because Favell was highly regarded after some good seasons in Philly. What was ignored by the Leafs was that Favell’s back problems were worse than thought.

    Favell’s contract was in the $60 K neighbourhood. Parent – the better goalie – would have signed for that amount or maybe a little more. He was not yet regarded as high as Tony O or Dryden – plus the Leafs had his NHL rights. Had it been only been left to Jim Gregory…Ballard didn’t save a dime and his petulance hurt the team – which was the pattern with Dave Keon, Paul Henderson, Darryl Sittler, Lanny McDonald, Laurie Boschman, _______….

    • I remember hearing about a lot of those background events as well. It makes me wish the Leafs had been able to find an owner like Ilitch. *sigh*

      • I confirmed elements of the basic story with Bernie Parent himself. The offer for less money ended any hope of him rejoining the Leafs. With Ballard out of the way, I’m sure Jim Gregory would have made an honest, reasonable offer and Bernie would have signed. No doubt he preferred returning to the Flyers for family reasons, but would have played for the Leafs, who had potential. Parent also told me playing in empty arenas in the WHA was difficult.

        If you think about the way Ballard treated the stars of the team of the early 1970’s – Keon, Henderson, Ellis and Ullman – he treated them like dirt and hurt the team by essentially getting nothing for them as they entered the downside of their careers. This is the reason the team of the late 1970’s with Sittler, McDonald, Salming & Turnbull lacked depth and never entered the top echelon of the league.

        To think that where the Leafs and Red Wings were in the mid 1980’s when Mike Illitch took over and where the teams are today is depressing for any Leaf fan…

        Yeah, the ownership started to become a problem with Ballard’s deeper involvement in the 1960’s. After Stafford Smythe died and Ballard gained majority control, things went really sour.

    • Totally missed that one; a quick looks shows the trade wasn’t THAT bad in retrospect: none of the draft picks were impact NHL plyaers, although Brent Peterson did play 600 NHL games. It definitely at the very least warranted a dis-honourable mention: good catch!

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