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The 25 Worst Trades in Modern Toronto Maple Leafs History

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02-13-2013, 02:24 PM
  #1
the1jasontaylor
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The 25 Worst Trades in Modern Toronto Maple Leafs History

Hello all,

A few years back (2008), some folks in this forum were kind enough to link to (and read through) a list I made of the worst trades in Leafs' history.

I recently completed a revised version of the list, and expanded it to a Top 25 list. As a disclaimer, I am a genuine Leafs' fan; I was even at the Gardens when Gilmour scored his famous wraparound goal against CuJo in 1993. So this isn't a Leafs-bashing enterprise from a sarcastic Habs fan, merely an honest look back by a disgruntled Leafs fan. Anyways, I've posted the list in the following sections (in case anyone would like to skim or read certain portions of it):
Introduction, #21-25, #16-20, #11-15, #6-10 and #1-5.

I had a lot of fun doing the research (especially into the ones that had lasting repercussions to the franchise), and even defended a few deals that get a bad rap sometimes.

I would love to get feedback from other hockey fans, be it positive or negative. I had a lot of fun writing the list, and I hope some fellow puckheads enjoy my writing.

I'm also working on a Best Leafs Trades list, no ETA as of yet. Anyways, I hope you enjoy it, and feedback is both welcomed and appreciated!


Last edited by the1jasontaylor: 06-11-2013 at 09:04 AM.
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02-13-2013, 03:14 PM
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LeBlondeDemon10
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Nice work. I think you'll complete the 'best trades' list a lot quicker.

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02-13-2013, 03:56 PM
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the1jasontaylor
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Nice work. I think you'll complete the 'best trades' list a lot quicker.
Sadly, that is proving to be the case; it looks like I'll have a solid Top 10, but pushing past a Top 15 could be dicey. There isn't much "meat" there is to a Best-Of list of Leafs' trades outside of the Top 10, and virtually NOTHING to choose from in the 70s and 80s. Other than getting Rick Vaive from Vancouver, the pickings are pretty slim until Cliff Fletcher arrived and shook things up (Fuhr, Gilmour, etc).

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02-14-2013, 09:29 AM
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tony d
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Good work here. That Kordic trade has to haunt Leafs fans to this day and it really should be higher on the list.

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02-14-2013, 09:41 AM
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Good work here. That Kordic trade has to haunt Leafs fans to this day and it really should be higher on the list.
Definitely.

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02-14-2013, 12:43 PM
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the1jasontaylor
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Good work here. That Kordic trade has to haunt Leafs fans to this day and it really should be higher on the list.
I could arguably see the Courtnall deal placing ahead of the Sullivan/Khristich clusterf**k, since each was about jettisoning a useful, skilled player more because they didn't fit in with the coaches' style (Brophy wanted a goon, and I believe Quinn thought Sullivan was too small/soft).

But I don't think you can place the loss of Courtnall ahead of Carlyle (Norris-trophy winner), Kehoe (perennial 30-goal scorer), Parent (HOF) or a Top-3 draft pick. Russ was good, but he wasn't an all-star (I think he only made one all-star game in 1994).

That being said, thanks for the feedback!

For an interesting take on the Courtnall trade, I recommend checking out a posting from Down Goes Brown that actually DEFENDS the Courtnall-Kordic swap.

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02-14-2013, 01:20 PM
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We need Mad Mike vs. the GMs of Toronto thread

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02-14-2013, 02:34 PM
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We need Mad Mike vs. the GMs of Toronto thread
Seriously, the talent that man traded away is MIND-BOGGLING. Luongo, Palffy, Bertuzzi, McCabe, Berard, Chara, Jokinen, Redden, Salo and I believe Karparaitus... wow. I'm surprised Islanders fans aren't more suicidal. Although with the team leaving I supposed they simply don't care anymore.

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02-14-2013, 03:37 PM
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Seriously, the talent that man traded away is MIND-BOGGLING. Luongo, Palffy, Bertuzzi, McCabe, Berard, Chara, Jokinen, Redden, Salo and I believe Karparaitus... wow. I'm surprised Islanders fans aren't more suicidal. Although with the team leaving I supposed they simply don't care anymore.
The Kasparaitis deal wasnt so bad. They traded him and Andreas Johansson for Bryan Smolinsky. Milbury didnt really get bad until after the 95-96 season. The Kenny Jönsson trade was probalby the last great trade he made.

In defense of Milbury though, he inherited an awful team with dodgy ownership. '96 was awful since the "stars" didnt want to play for the team. Never really like Muller after his primadonna act for that team. Schneider and Clark didnt really want to play there either and team morale was **** poor.

I dont think the bad thing was the asests he traded away but what he traded them for.

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02-14-2013, 05:01 PM
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Good work, and this is from someone's who's skeptical of anyone who doesn't condemn the Kessel deal, but at the same time, a proper evaluation of that deal won't be possible for another 5 years or so at least, until we see how everyone in the deal develops.

I like your take on the Vaive-Eddie O deal.


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02-15-2013, 08:55 AM
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Good work, and this is from someone's who's skeptical of anyone who doesn't condemn the Kessel deal, but at the same time, a proper evaluation of that deal won't be possible for another 5 years or so at least, until we see how everyone in the deal develops.

I like your take on the Vaive-Eddie O deal.

Basically, I see the Kessel trade as our overpaying for a quality player. There was, and isn't, anything wrong with Kessel being on the Leafs; he's a consistent 30-goal scorer in an era where those players are far too rare. Yes, we paid far too much for him, but for a deal to be TRULY horrid, the assets you acquire have to be devalued (such as a fading veteran) or worthless (such as a draft choice who never makes the NHL).

But you are absolutely right, this trade can't meaningfully be judged until all the players are at the point where they can be properly slotted in terms of their calibre as an NHL player (assuming all of the Boston prospects make it).

Thanks for the feedback on the Vaive-Olczyk deal! That was a trade that I imagine was TOUGH for Leafs' faithful to accept at the time, especially given Vaive's track record and captaincy. But it worked out like gangbusters. And it created quite an asset chain: Vaive --> Olczyk --> Ellett --> Sullivan, McCauley, Smith. Makes the Leafs' squandering of what New Jersey gave up for Gilmour/Ellett even more depressing!

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02-15-2013, 11:15 AM
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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.
Here's the way I remember it going down, when the Bruins walked away from the award.

The rule at the time was that if you walk away from an award, you retained right of first refusal on a contract worth 85% or less (something like that) of the original award. So effectively TOR gave BOS the pick so that they wouldn't match. Which was a bit strange since BOS clearly didn't want the guy. Probably that old boys club mentality between Quinn and Harry Sinden in terms of a "keep the peace" thing, similar to why there are not very many offer sheets.

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02-15-2013, 01:00 PM
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Sadly, that is proving to be the case; it looks like I'll have a solid Top 10, but pushing past a Top 15 could be dicey. There isn't much "meat" there is to a Best-Of list of Leafs' trades outside of the Top 10, and virtually NOTHING to choose from in the 70s and 80s. Other than getting Rick Vaive from Vancouver, the pickings are pretty slim until Cliff Fletcher arrived and shook things up (Fuhr, Gilmour, etc).
Which is why a similar top 25 bad trades list for the Canucks would make me puke in my mouth, even Ballard era Leafs made us look bad...

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02-15-2013, 01:04 PM
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Originally Posted by the1jasontaylor View Post
Seriously, the talent that man traded away is MIND-BOGGLING. Luongo, Palffy, Bertuzzi, McCabe, Berard, Chara, Jokinen, Redden, Salo and I believe Karparaitus... wow. I'm surprised Islanders fans aren't more suicidal. Although with the team leaving I supposed they simply don't care anymore.
I think Trading Luongo and Jokinen for Kvasha and Parrish so that they could draft Dipietro over Heatley has to be the worst roster management ever. Most bad trades were defensible at the time. That was always stupid.

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02-15-2013, 01:12 PM
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The Rask deal has to be higher, as it has been more devastating to the franchise than putting Sullivan on waivers. The Leafs had two goalies in developmental, and there was really no reason to trade one of them off in 2006. Rask was still in the Finnish League, and Pogge had yet to play in the AHL. Basically, neither goalie was blocking the other one from playing, so it would have been beneficial to the team to at least see what they had. In Raycroft's last season with Boston, he had a .879 SV%. An absolutely terrible season, and though he was only a season removed from his Calder year, there was doubt on whether he could regain his form. Basically, he shouldn't have cost a Rask.

Just think of how different the Leafs would look right now with Rask, provided he developed into the same goaltender. Even if the Kessel deal gets done, it's doubtful the Leafs finish as low as they did, as you would have to assume that stable goaltending in 09-10 would have pushed them out of the basement, and even better in 10-11. The team won a lot more with James Reimer in the second half of 10-11, and they slowly rose from the basement.

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02-15-2013, 01:56 PM
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Originally Posted by bruins309 View Post
Here's the way I remember it going down, when the Bruins walked away from the award.

The rule at the time was that if you walk away from an award, you retained right of first refusal on a contract worth 85% or less (something like that) of the original award. So effectively TOR gave BOS the pick so that they wouldn't match. Which was a bit strange since BOS clearly didn't want the guy. Probably that old boys club mentality between Quinn and Harry Sinden in terms of a "keep the peace" thing, similar to why there are not very many offer sheets.
Hmm, I hadn't heard that. I thought I remembered Damien Cox from
the Toronto Star stating that the Bruins were ABOUT to walk away, in which case the player becomes a UFA. I was under the impression that refusing an arbitration award meant you forfeited rights to the player. But I can't find a conclusive answer either way. But if you're right, I'm SURE the Leafs could have given up less than a second round pick; the Bruins were SUPER cheap which is why they kept losing star players during that time. They wouldn't have matched.


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Which is why a similar top 25 bad trades list for the Canucks would make me puke in my mouth, even Ballard era Leafs made us look bad...
I'm actually eying a Top 15-25 Worst Trades for each of the Canadian franchises. Every team has the "one that got away" or that trade where they got fleeced; Neely (VAN), Gilmour (CGY), the majority of the dynasty dismantling (EDM), Demitra (OTT), LeClair (MTL) and Selanne (WPG). Although, personal bias being what it is, I'd LOVE to put together a Habs list and cause some mental anguish for that fanbase. =)


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Originally Posted by Nalyd Psycho View Post
I think Trading Luongo and Jokinen for Kvasha and Parrish so that they could draft Dipietro over Heatley has to be the worst roster management ever. Most bad trades were defensible at the time. That was always stupid.
He's Mad Mike for a reason. Although I'd put the Kurvers/Lindros saga ahead of ANY terrible Islanders deal.


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Originally Posted by popculturereference View Post
The Rask deal has to be higher, as it has been more devastating to the franchise than putting Sullivan on waivers. The Leafs had two goalies in developmental, and there was really no reason to trade one of them off in 2006. Rask was still in the Finnish League, and Pogge had yet to play in the AHL. Basically, neither goalie was blocking the other one from playing, so it would have been beneficial to the team to at least see what they had. In Raycroft's last season with Boston, he had a .879 SV%. An absolutely terrible season, and though he was only a season removed from his Calder year, there was doubt on whether he could regain his form. Basically, he shouldn't have cost a Rask.

Just think of how different the Leafs would look right now with Rask, provided he developed into the same goaltender. Even if the Kessel deal gets done, it's doubtful the Leafs finish as low as they did, as you would have to assume that stable goaltending in 09-10 would have pushed them out of the basement, and even better in 10-11. The team won a lot more with James Reimer in the second half of 10-11, and they slowly rose from the basement.
You do raise some valid points, and I was tempted to put Rask higher. But the problem is he's still leaning towards the "potential" side of the equation; this is his first year as The Man, without being part of a tandem with a veteran star like Tim Thomas. While he is proving himself, and I have no doubt he will be a long-term star in the NHL, he isn't there yet. Plus even with Rask in the farm, Ferguson would've still likely made the Toskala trade or something similar.

I agree with you 100% on the warning signs around Raycroft and the high cost. Just like the Leafs always seem to fleece the Flames, for some reason Boston ALWAYS has Toronto's number in trades. The only "wins" that come to mind are the Kaberle trade and the Tom Fergus-Bill Derlago swap in the 80s.

Rask with Reimer as a back-up would have the Leafs in a FAR better situation, and having Rask stay with Toronto could have helped Pogge develop with less pressure. It didn't help that management never showed any faith in the poor kid; didn't Scott Clemmensen get all the starts when the Marlies had a deep playoff run one year?

The Leafs have had two pressing needs since the lockout: a #1 goalie post-Belfour, and a #1 centre post-Sundin. Neither has ever truly been addressed.

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02-15-2013, 02:50 PM
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Originally Posted by the1jasontaylor View Post
You do raise some valid points, and I was tempted to put Rask higher. But the problem is he's still leaning towards the "potential" side of the equation; this is his first year as The Man, without being part of a tandem with a veteran star like Tim Thomas. While he is proving himself, and I have no doubt he will be a long-term star in the NHL, he isn't there yet. Plus even with Rask in the farm, Ferguson would've still likely made the Toskala trade or something similar.

I agree with you 100% on the warning signs around Raycroft and the high cost. Just like the Leafs always seem to fleece the Flames, for some reason Boston ALWAYS has Toronto's number in trades. The only "wins" that come to mind are the Kaberle trade and the Tom Fergus-Bill Derlago swap in the 80s.

Rask with Reimer as a back-up would have the Leafs in a FAR better situation, and having Rask stay with Toronto could have helped Pogge develop with less pressure. It didn't help that management never showed any faith in the poor kid; didn't Scott Clemmensen get all the starts when the Marlies had a deep playoff run one year?

The Leafs have had two pressing needs since the lockout: a #1 goalie post-Belfour, and a #1 centre post-Sundin. Neither has ever truly been addressed.
I guess I should have ended my post with the question, "am I right to assume that if this list was to be updated in five years, assuming Rask stays as one of the better goaltenders in the league, that you would place the trade higher?" In this post, you seem to be saying that.

But, yeah, before I edited my last post, I did talk a little about the Toskala trade. It probably would have happened. If the Leafs don't get Raycroft, and settle on whoever was available in free agency, they probably would have made the playoffs in 06-07 (Raycroft started 72 games with a .892 SV%. My guess is that even a .900 SV% in those games would have given them an extra win or two, which would have put them in the playoffs). So basically, you still have a team with huge issues, but a team that thinks it's a playoff team, which would still probably lead to the Toskala deal (or, like you said, something similar). The team would still suck, and it's probable the Leafs wouldn't have let Rask develop as slowly as he did, but at least the Leafs would have an answer for the long-term future.

Again, in my revisions, I assume that Rask develops into the same player. As for Pogge, I don't remember Clemmensen starting over him in the AHL playoffs, but Hockey-Reference tells me he started 17 games during the Marlies 07-08 playoff run. I am now vaguely remembering this, but it's been so long, and something I haven't thought of since that time, that I can't really comment.

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02-15-2013, 04:34 PM
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Great read, well written and really insightful. Nice work

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02-15-2013, 04:42 PM
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Nice work. I think you'll complete the 'best trades' list a lot quicker.
and I will argue to I am blue in the face that the Vaive/Delego deal for Tiger williams was not as big as a win for the Leafs--Tiger got the nucks to the cup finals, something Vaive did not with the leafs

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02-15-2013, 05:55 PM
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really enjoyed reading that. Would love to see the same effort behind the best/worst trades of every NHL franchise.

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02-15-2013, 06:17 PM
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Nice list. I never knew about a lot of those trades from the 70's / early 80's.


Rick Kehoe for Blaine Stoughtoin + 1st was technically actually a good trade, just bad player development. Blaine Stoughton was quite possibly one of the best rebound/garbage goal guys in the history of the NHL. I think he held the Whalers/Hurricanes single season scoring record for 20+ years.


I never knew Doug Jarvis was drafted by the Leafs. Wow, that's a bad one.


Leafs should write something into the bylaws outlawing trading #1 draft picks.

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02-15-2013, 06:36 PM
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For an interesting take on the Courtnall trade, I recommend checking out a posting from Down Goes Brown that actually DEFENDS the Courtnall-Kordic swap.
I liked Courtnall, but the way that he's somehow remembered as an excellent scoring forward is removed from reality. He was basically a better version of Jason Chimera. He had superlative speed, he had average hands, and wasn't physical or really defensively oriented. He'd show enough flashes to get put on the top two lines, but wasn't really an All-Star at any point (except for one year, when I believe he was an injury replacement).

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02-15-2013, 09:06 PM
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For an interesting take on the Courtnall trade, I recommend checking out a posting from Down Goes Brown that actually DEFENDS the Courtnall-Kordic swap.
Courtnall for Kordic was an exchange of two players with similar off-ice issues, only one player destroyed himself in very public fashion while the other kept his issues mainly under the radar until sorting himself out a decade later.

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02-16-2013, 09:14 AM
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Kessel for 2 first round picks be worse to me

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02-16-2013, 11:02 AM
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I liked Courtnall, but the way that he's somehow remembered as an excellent scoring forward is removed from reality. He was basically a better version of Jason Chimera. He had superlative speed, he had average hands, and wasn't physical or really defensively oriented. He'd show enough flashes to get put on the top two lines, but wasn't really an All-Star at any point (except for one year, when I believe he was an injury replacement).
I remember him more as a guy who should have been better. He had the physical tools, and occasionally he'd show flashes of elite skill, and occasionally he played like he cared about the outcome of the game. But mostly, he just seemed to enjoy skating.

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