The 25 Worst Trades in Toronto Maple Leafs History: #11 to 15

Links to the other individual articles in this series: Intro, #21-25, #16-20, #6-10, #1-10

Welcome to Part Four in a series examining the worst trades in Toronto Maple Leafs history.  We’re getting to the mid-point of the list, and the trades are getting darker.  But any Bruins fans will start feeling even better about themselves for sure.  Please “enjoy” #15 through #11 of the Top 25 Worst Toronto Maple Leafs trades of the modern era.

#15: Toronto trades Tuukka Rask to the Boston Bruins for Andrew Raycroft (June 24th, 2006)
When I put this trade on my original list in 2008, here is what I wrote prior to Rask playing a single NHL game:

“I knew the SECOND (the Leafs) traded for Raycroft that it was a mistake.  NO Bruins’ goaltender since Andy Moog has ever been good for more than 18 months.  Jon Casey, John Blue, Blaine Lacher, Jon Grahame, Byron Dafoe, Bill Ranford (the second time), Jim Carey (not the actor)… the list goes on.  And you can add Raycroft to this list.  If Rask even turns out to be HALF as good as people (think), this trade will still belong on this list.”

I’m quite proud of that, if I do say so myself (and this is my website, so I do say so).  Although his durability is a little questionable, Rask still unseated Tim Thomas, a Vezina winner and fan-favourite in Boston (prior to a mental meltdown during the 2012 U.S. election season, anyways).  Rask has been incredible for the Bruins.  As of the start of the 2012-13 season, Rask has gone 47-35-11 with 11 (!) shut-outs, a 2.20 GAA and a .926 save percentage.  Now it remains to be seen if Rask can put up a strong year as “the man” in Boston, without Thomas as a safety net.  He will be hard-pressed to prove he’s not just another in a long line of failed Boston goaltenders.  But the fact remains that the Leafs thought Justin Pogge was going to be the better keeper… and they dealt Pogge to Anaheim for a “conditional pick” in the summer of 2009.   He played just seven games for Toronto in 2008-2009, and hasn’t made it past the AHL level since (even playing in the ECHL for short stint).  Even if Rask flames out, he’s still provided a high quality level of goaltending that hasn’t been seen in Toronto since the crease lineage of Fuhr-Potvin-Joseph-Belfour was interrupted by the ’04-05 lockout.

I can understand the appeal of Andrew Raycroft to ex-Leafs’ GM John Ferguson Jr. at the time (somewhat).  Raycroft won the Calder trophy in 2003-04 as the NHL’s rookie of the year.  He struggled in the first season after the lockout, but that can be common as scouts and competitors learn a young upstart’s tricks and tendencies.  Ferguson likely thought he was getting an under-valued asset.  But to give up a PRIME prospect like Rask for an uncertainty like Raycroft… that’s not brave, that’s reckless.  And that is evidenced by the fact that all we have to show for trading one of the most promising goalies in the NHL is 91 games over two sub-par seasons from Razor, a man whose post-Toronto career has seen him fail to play more than 31 games in a season for any of his three NHL teams (over a four-year period), before he finally ended up playing in Italy.  The Leafs would have been better off hedging their bets by keeping Pogge AND Rask in the minors to push each other, and then signing a stopgap solution like Mike Dunham to fill until one of them became a the #1 guy post-Belfour.  But Ferguson was trying to save his job, and no one in management was thinking long-term:  they were thinking of a few more lucrative home playoff gates.  And wouldn’t you know it, I think the last one we saw at the ACC was back in 2004.  The last time Andrew Raycroft was considered an NHL-calibre starting goaltender.  Ugh.

#14: Toronto trades Kenny Jonsson, Sean Haggerty, Darby Hendrickson and a 1st Round Pick in 1997 (Roberto Luongo) to the New York Islanders for Wendel Clark, Mathieu Schneider and D.J. Smith (March 13th, 1996)
Many people will see this trade ranked “only” #14 on my list, and point out that this trade gifted Roberto Luongo to the Islanders.  Now the Islanders completely squandered Luongo’s talents, but that’s a story for another day (note to self: begin researching the Top “Mad” Mike Milbury trades).  However, I will ignore that for one very simple reason: there is no guarantee that the Leafs would have selected Luongo in the draft.  Now if the Leafs had owned Luongo’s rights and THEN traded him to New York, this trade would be much higher up the list.

In order to understand this trade, you must understand its context.  Leafs fans decried the loss of Clark (despite the fact that the man acquired in return, Mats Sundin, ended up being possibly the best Leaf of the past 20 years, though Gilmour fans would argue otherwise).  As such, they were practically screaming for Clark to return to Toronto, and ownership unfortunately relented.  In the short-term, it looked like a good move: Clark scored 15 points in 13 games after being re-acquired, then followed that up with 30 goals in the 96-97 season.  But then-Leafs’ GM Cliff Fletcher apparently turned down a 1st Round Pick from the Pittsburgh Penguins in exchange for Clark, uttering his infamous “draft-shmaft” quote.  Clark then turned in a mediocre 47-game, 19-point season before leaving Toronto as a free agent for Tampa Bay.  For which the Leafs received… nothing.  Yeah, why have a first rounder (possibly) turn into a blue-chip prospect when you can keep your fan-favourite for one more injury-plagued year and then let him WALK???  As for the other players in the deal, Schneider was injured most of the 96-97 season, but decent overall: he recorded 56 points in 115 games as a Leaf.  D.J. Smith had a cup of coffee as a Leaf (11 games, 1 assist), before being dealt as part of a package for Marc Moro (who put in five solid years… for Toronto’s AHL teams).

As for New York, Haggerty was a bust, playing in just 10 games for the Islanders (and only 14 NHL games total).  Hendrickson only played 16 games before being shipped back to Toronto.  Kenny Jonsson, however, was a fixture on the Islanders’ blueline for a decade.  He played 597 games for New York, recording 232 points: many of them over a period where quality Leafs’ blueliners were few and far between.  Never mind the first rounder that turned into Luongo.  Jonsson was a rare gem: a Leafs’ draft pick who blossomed into a quality hockey player for nearly a decade.  Granted, not an all-star, but he was better than the vast majority of Leafs’ defensemen who played during his career.

The only reason this trade isn’t closer to the Top 10 is because the Leafs actually managed to do some decent asset management: Schneider became Alexander Karpovtsev, who in turn became Bryan McCabe.  So the Leafs still got a number of decent seasons on their blueline in the end.  But this was an awful trade done for the wrong reasons, compounded by the fact that the Leafs could have recouped their lost first rounder, but instead chose to let Wendel walk for nothing.  Draft-shmaft indeed.

#13: Toronto allows Craig Muni to become a Free Agent; Muni signs with the Edmonton Oilers (August 18th, 1986)
DISCLAIMER: I realize I’m putting a free agency departure on a “worst-of” trade list, but this came at a time when it was very rare for free agents to change teams without any sort of compensation.  Therefore, I’ve decided to include it.

Craig Muni isn’t someone many Leafs fans think of as an ex-Leaf, and I was also guilty of that when I did this list the first time around.  The Leafs chose Muni in 2nd round of the 1980 Entry draft, 25th overall.  Despite the high selection, he was never able to stick with the big club, playing just 19 games between the 1981-82 and 1985-86 seasons.  The Leafs let him play the majority of his games with the AHL’s St. Catharines Saints and, when Muni’s contract ran out, they opted to let him go.  Muni ended up signing a contract with none other than the Edmonton Oilers, and never looked back.  He scored 29 points and was a whopping +45 in 86-87 with the Oilers, winning a Stanley Cup ring.  He added two more with Edmonton in 1988 and 1990, and remained a staple on their blueline until he was traded to the Blackhawks in March of 1993.  He bounced around with a few other clubs before retiring after the 1997-98 season.

Let’s consider that for a moment.  In a COMPLETE departure from their typical development strategy in the 1980s, the Leafs allowed a highly-drafted young defenseman to mature in the minors instead of being rushed to the NHL (see Jim Benning, Gary Nylund, Al Iafrate, Luke Richardson and many more).  His AHL numbers actually indicated some decent two-way potential: Muni recorded 38, 20, 24 and 37 points in four seasons with St. Catharines.  Whatever you may think of Glen Sather and his tenure with the New York Rangers, the man was unreal in Edmonton.  He oversaw the drafting of several Hall of Famers (Kurri, Coffey, Messier, Fuhr, etc.), but he also unearthed some real free agent gems: Craig MacTavish was signed in 1985 after a year out of the NHL (spent in prison).  MacTavish rewarded Sather’s risk, playing nearly nine years with the Oilers (four times scoring 20+ goals, and winning three Cups alongside Muni).  Randy Gregg is another example: he was signed in 1982, and played on all five Cup-winning teams in Edmonton.  Muni was an asset that the Leafs seriously under-valued, as evidenced by the fact that he played 800 NHL games after leaving Toronto.  While I acknowledge that this was not a trade, it was still a decision to let a home-grown prospect leave for absolutely nothing in return at a time when free agent compensation was largely in favour of the team that lost the player (e.g. Scott Stevens, Brendan Shanahan).  No matter how you look at it, letting Muni walk was a terrible decision.

#12: Toronto allows the Boston Bruins to claim Gerry Cheevers in the NHL Intra-League Draft (June 9th, 1965)
As with Craig Muni at #13, this technically isn’t a trade.  And its 1965 date puts it on the wrong side of my “modern era” cut-off.  But I feel it should be brought to Leafs fans’ attention, so I’m including it under a Public Service exemption!  The Leafs made a conscious decision to keep other assets, and allowed Cheevers to leave without receiving any compensation, which is why I included it on this list.  Now I understand that the Leafs left Cheevers unprotected in order to keep both Johnny Bower and Terry Sawchuk, the goaltending tandem that won the Leafs their most “recent” Stanley Cup in 1967.  But surely there was another way?  Perhaps they could have made a deal with Boston to get Cheevers back, or perhaps they could have exposed Sawchuk and then re-acquired him.  For example, the Vancouver Canucks traded Doug Lidster to the New York Rangers prior to the 1994 Expansion Draft for John Vanbiesbrouck; the Florida Panthers then selected Beezer, which allowed the Canucks to keep then-highly-regarded Kay Whitmore as their back-up goalie behind Kirk McLean.  So it can be done.

To say that Gerry Cheevers did well in Boston would be an understatement of epic proportions.  He was a key part of Boston’s two Stanley Cup-winning squads in 1970 and 1972.  He was also a risk-taker, jumping immediately from the 1972 Cup win to the WHA.  Cheevers he spent nearly four seasons with the Cleveland Crusaders, and was on the WHA’s 1974 Summit Series team.  He then came back and played in parts of five seasons with the Bruins, participating in the 1979 Challenge Cup.

In total, Cheevers posted an NHL record of 230 wins, 102 losses and 72 ties in 418 games, and won a remarkable 53 of 88 playoff games with the Bruins (a 60% success rate).  Plus he designed quite simply the coolest, and possibly most iconic goalie mask of all time.  And he left Toronto for absolutely nothing.  I can’t be the only one who wonders just how incredible the Leafs would have been with a tandem of Gerry Cheevers and Bernie Parent (who is coming up later on this list) in net during the 1970s.

#11: Toronto trades Lanny McDonald and Joel Quenville to the Colorado Rockies for Pat Hickey and Wilf Paiement (December 29th, 1979)
Simply put, this trade was one that began the franchise’s descent into the hell that was the 1980s.  Between 1979-80 and 1989-90, the Leafs had a record of 301-481-98, a win percentage of just .398.  Furthermore, they surrendered 660 more goals than they scored, which is an average of 60 per season or roughly 0.75 goals per game.  It was reported that this deal was also part of an ongoing war between Punch Imlach and Leafs’ Captain Darryl Sittler, and that it was done to remind Sittler who was in charge.  Only in Toronto would a personal vendetta come before the success of the club.  If anyone ever tried that in Montreal, they’d be run out of town with torches and pitchforks.

At first, Pat Hickey was an unexpected bonus, scoring 22 goals in just 45 games during his first half-year with the club.  But the next season he was quite ordinary (16 goals and 49 points), and one game into the 81-82 season he was gone.  Joel Quenville, Hickey’s counterpart in the trade, was a serviceable defenseman for Colorado.  Quenville even followed the club when it moved to New Jersey.  In total, Quenville played 710 games after leaving the Maple Leafs.

At first glance, the exchange of star players worked out well.  Paiement scored 203 points in 187 games for Toronto, while McDonald contributed 141 points in 142 games as a member of the Colorado Rockies.  Paiement even recorded a stellar 40 goals and 97 points in his first full season in Toronto.  But when he dropped to 18 goals and 58 points the following seasons, the Leafs traded him to Quebec for Miroslav Frycer and a 7th round pick (that became Jeff Triano).  Yes, you read that right; within about 18 months, all the Leafs had to show for trading heart-and-soul player Lanny McDonald… was Miroslav Frycer.  It also hurts that Colorado didn’t fare much better with their asset turnover: they dealt McDonald to Calgary, where he played another 492 games, scored another 215 goals and 406 points (including 66 goals in 1982-83), and won a Stanley Cup in his final season (1988-89).  Ironically, Joel Quenville ended up in Calgary as well.

This trade is #11 for a pair of reasons.  Firstly, looking at the numbers, the trade isn’t as god-awful as I had originally expected.  Paiement’s contributions in Toronto were actually superior to McDonald’s in Colorado, and the Rockies traded McDonald away for spare parts Bob MacMillan and Don Lever.  So both teams were guilty of squandering assets.  But what keeps this trade relatively high up the list is the fact that the Leafs were TRYING to shoot themselves in the foot simply to hurt their captain and superstar, AND they squandered the resources they received (Paiement) for a player (Frycer) who was at best a decent forward on some of the worst Leaf teams of all time.  And so this intentionally terrible deal falls just outside of the Top 10 unintentionally terrible trades.

That’s all for Part Four, and here’s Part Five, detailing the trades ranking #6-10!

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2 thoughts on “The 25 Worst Trades in Toronto Maple Leafs History: #11 to 15

  1. #11 is not a terrible trade. Edge to Colorado but not a worst trade listing IMO. Mcdonald was a solid player but overrated by Leafs fans. Paiement was just as good a McDonald (at the time) and actually had a better points per game numbers as a Leaf. McDonald I think peaked in Calgary. Quenville & Hickey equal out. Good pros.

    The idea that Punch made the trade to destroy the Leafs is not correct. Read Imlach’s book. His opinion of the Leafs stars of that era is a little more accurate than that of romanticizing fans. Salming was on the downside. It was a country club atmosphere where players where treating like gods for finishing in 7th place and winning A playoff series. The real problem was the conflict between Sittler and Imlach. It depends upon whose view you look at. Sittler thought Imlach was trying to get rid of his allies in the dressing room, Punch thought the Captain seemed more concerned about losing friends than building a real winner. It soon became poisonous. But don’t believe just the Sittler side of the story. Most fans loved Sittler and backed him completely. But if he supported Imlach instead of fighting him, the team never would have been torn apart and fallen so low. And what was Sittler’s responsibility to the Leafs as Captain? Team first, right.

    BTW good read. Lots of work you put in. I’ve enjoyed the chapters.

    • The trade wasn’t one-sided in favour of Colorado, as McDonald (141 points in 142 games for Colorado) was more-or-less an even trade-off with Paiement (203 points in 187 games for Toronto). But Paiement contributed 275 points in 367 games post-Toronto, while McDonald had 406 points in 492 games. McDonald also had a a monster 66-goal, 98-point season in ’82-83, just two-and-a-half seasons after leaving Toronto. Paiement had 39 goals and 76 points in ’83-84, but then fell steadily and was out of the league early in ’87-88. Lanny’s production also fell off, but he still fit a player-coach role on the Flames up to their 1989 Stanley Cup victory. He also had 18 points in 22 games during their run to the 1986 Cup Finals. So I rated the trade as a bad one not necessarily because of how the trade benefitted Colorado: you’re right, the trade netted out evenly for both teams. But McDonald and Quenville played 958 games post-Rockies and 386 games in Colorado: by comparison, the Leafs got 305 games from Hickey/Paiement and those players played in 552 games post-Toronto. The Leafs sacrificed longer careers at a higher skill level than what they received in the deal.

      Interesting feedback regarding Imlach, I didn’t even realize he HAD a book. I dispute Salming being on the downside, he scored 39 points in ’84-85, and was still chipping in 20+ points with positive +/- ratings from ’86-87 to ’88-89 (albeit in injury-shortened seasons). But you’re right, I did take the Sittler stance that the McDonald trade was done to demoralize Sittler and remove some of his leverage. But that’s the viewpoint echoed by most material I’ve read on that era (which may or may not include Salming and Gord Stelllick’s books… both of which I read many years ago, but can’t recall very much of). But I definitely don’t dispute your mention of a “country club” atmosphere: “blue and white disease” has been an epidemic in Toronto forever.

      Awesome feedback, thank you for sharing!

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