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15 Worst Trades in Maple Leaf History (Part 1 of 3)

2013 UPDATE: I have refreshed and expanded this list on another website.  Check out the series here: Introduction, #21-25, #16-20, #11-15, #6-10 and #1-5.

I know this blog is pop-culture focused, but sports are definitely a part of popular culture.  And one sport that struggles for popularity outside of a few stronghold countries is hockey.  But like any sport, there are a few teams that are institutions.  Baseball has the Yankees, basketball has the Lakers and Celtics… hockey has the Original Six teams.  And possibly the most painful of those teams to be a fan of is the Toronto Maple Leafs.

The picture above shows the four most popular Leafs captains of the past 30 years.  None of them were allowed to retire as Leafs captain, and two of them were dealt in such brutal trades that they fall into the list which begins shortly.  You see the Leafs were once a storied NHL franchise, rich in success, talent and Cup wins.  A number of factors helped contribute to their downfall; then the NHL began expanding, the rival World Hockey Association began siphoning off talented players, and the infamous Harold Ballard took over as majority owner and drove what little pride remained from Maple Leaf Gardens.  Some teams would be able to persevere through these challenges, if they can continue to make smart personnel moves.   Unfortunately… the Leafs have made more than their share of bad trades since they won their last Stanley Cup some 40 years ago.  Here are the first “highlights” from that group.

DNQ: Toronto trades Rick Vaive, Steve Thomas and Bob McGill to the Chicago Blackhawks for Ed Olczyk and AL Secord
This trade is mentioned frequently as an awful trade, due to Vaive’s success with the team (and the fact that he is one of only two players to score 50 goals in a single season wearing a Leafs jersey).  However, the numbers tell a different story.  Vaive played just 106 games in Chicago, scoring 55 goals, before being dealt to Buffalo, where he was a shadow of his former self, and he faded away a few seasons later.  Thomas was strong for the Blackhawks, but not a star; he recorded 198 points in 231 games before being shipped off to the New York Islanders.  Bob McGill was servicable, but didn’t do much of note in four seasons with Chicago.

Now Al Secord was a mistake to acquire, one which the Leafs rectified just a year and a half later by shipping him to Philadelphia.  But Ed Olczyk was spectacular.  He averaged 37 goals and 84 points in his 3 full seasons with Toronto.  And when he was traded to Winnipeg, he netted the Leafs Dave Ellett, who was a huge component of the beloved ’92 and ’93 Leafs teams.  Given Olczyk’s performance and Vaive’s disctinct lack of staying power post-Leafs, I’d actually call this trade a win rather than a loss.  And ironically enough, everyone but Vaive ended up having a second stint with the team that traded them (Olczyk and Secord played again in Chicago, while Thomas and McGill were Leafs in the 90s).

Dis-Honourable Mention: Toronto trades Alyn McCauley, Brad Boyes and a 2003 1st Round Pick (Mark Stuart) to the San Jose Sharks for Owen Nolan
People talk about this trade like it was the end of the world.  I will freely admit, losing McCauley (hero of the 2002 playoff run) sucked, as he has turned into a terrific defensive player.  But he wasn’t critical to the team.  And while Brad Boyes was a 40-goal scorer last year with St. Louis.  But he has never been anything above average until last year, and he’s been traded twice SINCE this deal.  And Mark Stuart was a bust, never even playing for San Jose.  Owen Nolan’s pickup was heralded as the “right move” in 2003 because of his strong clutch play and leadership reputation.  Yes he bombed, and yes he had a bitter divorce with the team due to injury lawsuits.  And his acquisition was a mistake.  BUT… it isn’t bigger than the 15 mistakes coming up next.  And on a side note, it is intensely depressing that Boyes was the first NHLer drafted by Toronto to get 40 goals in a season since Wendel Clark, who was drafted in what, 1986?  So very, very sad…

#15: Toronto trades Tukka Rask to the Boston Bruins for Andrew Raycroft
I will fully admit that I have some bias here.  I knew the SECOND we 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 thing, this trade will still belong on this list.  And it’s not the first time Toronto gifted a great goaltender to Boston.

#14: Toronto loses Gerry Cheevers to the Boston Bruins in the Intra-League Draft
Okay, so technically this isn’t a trade.  And losing Cheevers was necessary to keep both Johnny Bower and Terry Sawchuk, the goaltending tandem that won the Leafs the Stanely Cup in ’67.  But come ON, did they have to let Gerry CHEEVERS go?  The guy won two Stanley Cups with Boston, helped win the Summit Series against the Soviet Union in 1972, posted a record of 230 wins, 102 losses and 72 ties  in 418 games, and won FIFTY-THREE of 88 playoff games with the Bruins.  And he came up with the coolest goalie mask ever.  How could they let him go for NOTHING???

#13: Toronto trades Fredrick Modin to the Tampa Bay Lightning for Cory Cross and a 7th Round Pick in 2001 (Ivan Kolozvary)
I was hesitant to put this on the list, because I sincerely doubt Modin would ever have developed into a decent hockey player in the hockey fishbowl that is Toronto.  However, he developed into a solid forward for Tampa Bay,  averaging 24 goals a season over six years with the club, including three seasons of 50+ points and two 30-goal seasons.  You know, the kind of seasons one needs from decent offensive wingers, which have been sorely lacking from Toronto for a number of years.  Meanwhile poor Cory was a healthy scratch half the time, and despised by many fans the other half of the time.  Funny story; I attended a game in Tampa during the late 90s between Florida and Tampa.  8 fights, 3 of them involving Enrico Ciccone.  These four guys in front of me were riding Cory ALL night, taunting him every time he touched the puck.  Anyways, on one play a Lighting player was hit VERY hard into the glass and knocked out, leading to a huge brawl.  The arena erupted into jeers and everyone was pumped up.  All of the sudden, one of the four guys went “Oh its okay, it was only Cory.”  And all four promptly sat back down again, calmly sipping their beers and waiting for play to resume, despite the rest of the arena calling for blood.

#12: Toronto trades Larry Murphy to the Detroit Red Wings for Future Considerations
This trade irks me to no end.  Toronto traded for Murphy from Pittsburgh, and the guy recorded 60 points.  As a DEFENSEMAN.  And Leaf fans rode him mercilessly.  I’m pretty sure the last Leaf defenseman to do that was Al Iafrate in 89-90, and I don’t think it happened again until Bryan McCabe two seasons ago (and look how beloved he is).  Anyways, the Leafs were SO desparate to get rid of Murphy that Detroit simply had to pay 2/3 of what was left on his contract.  That’s right; the Leafs paid 1/3 of Murphy’s salary AND got nothing in return.  And all he did was score 171 points over the next four seasons and win two Stanley Cups.  And DURING those two Cup wins, he scored 26 points in 42 games for the Wings.  ARGH.


#11: 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.
Okay, first off you can COMPLETELY ignore the fact that the Islanders selected Luongo.  There is no guarantee that the Leafs would have picked him.  Had the Leafs owned Luongo’s rights and traded HIM to New York, then this trade would be much higher on the list.  Anyways, fans were SCREAMING for Wendel to return to Toronto, and ownership sadly listened.  Clark got 15 points in 13 games after returning, and then scored 30 goals the next season.  But Fletcher alledgely turned down an offer of a 1st rounder from Pittsburgh for Clark that year, uttering the infamous “draft-shmaft” quote.  Clark played one more mediocre season in Toronto before leaving as a free agent.  Meanwhile, while Haggerty was a bust and Hendrickson was back in Toronto the next season, Kenny Jonsson was a fixture in New York for a decade.  He played 597 games for New York, recording 232 points, many of them in a time where quality Leafs blueliners were few and far between.  Never mind the first rounder; Jonsson was a rare gem; a Leafs draft pick that blossomed, and played quality hockey for nearly a decade.  Mathieu Schneider is the only reason this trade wasn’t in the “Top” 10; he was solid for the Leafs, and then traded for Alex Karpovtsev, who in turn brought in Bryan McCabe.  Still, an awful trade compounded by the fact that Clark walked for nothing, and he could have brought a first rounder back.

I know this was a longer read for a blog, but like I said; I’m a long-time Leafs fan, and this blog has finally given me a forum to vent on just how frustrating it can be to BE a Leafs fan at time.  I hope you’ve enjoyed Part 1; Part 2 (Trades #6-10) is posted here, and Part 3 (Trades #1-5) is posted here.  Feedback is always welcome!

2013 UPDATE: I have refreshed and expanded this list on another website.  Check out the series here: Introduction, #21-25, #16-20, #11-15, #6-10 and #1-5.

July 28, 2008 Posted by | Sports | , , , , , , , , , | 7 Comments