Seemingly lopsided trades where the "loser" ended up winning the deal

Leafs87

Mr. Steal Your Job
Aug 10, 2010
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I’m going to be this guy too.

Kessel for Seguin, Hamilton and knight. 9 years later.

Leafs have to show for it Kapanen, Andersen and Greenway. A top 9 forwar with still decent up side. A starting goalie who some view as a top end starter. A meh prospect that probably won’t equate to much.

Bruins have to show for it Zach Seneshyn, Forsback-Karlsson and Louzon. More time needed but at the moment neither seem like more than top 9 forwards or bottom pairing D at best.
 

Leafs87

Mr. Steal Your Job
Aug 10, 2010
14,765
4,855
Toronto
A bit off topic, but since Melnyk is being discussed. I'm really tempted to email the NHL and ask if he violated the apperal deal by wearing the Reebok uniform in a team-sanctioned interview.

Damn the guy doesn’t even own an up to date version of his own teams jersey :laugh:

Btw sorry for derailing this thread !
 

93LEAFS

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Nov 7, 2009
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I’m going to be this guy too.

Kessel for Seguin, Hamilton and knight. 9 years later.

Leafs have to show for it Kapanen, Andersen and Greenway. A top 9 forwar with still decent up side. A starting goalie who some view as a top end starter. A meh prospect that probably won’t equate to much.

Bruins have to show for it Zach Seneshyn, Forsback-Karlsson and Louzon. More time needed but at the moment neither seem like more than top 9 forwards or bottom pairing D at best.
They also have a Stanley Cup to show for it. I think most leafs fan would trade anyone on our team for one of those.
 

LeafsNation75

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They also have a Stanley Cup to show for it. I think most leafs fan would trade anyone on our team for one of those.
With the exception of Game 2 of the Eastern Conference Final against Tampa Bay in 2011, it's not like Seguin had that much of an impact on the Bruins winning that year. In 2013 when he was no longer a healthy scratch in the playoffs and him playing more of a bigger role, the Bruins lost in the Stanley Cup Final.
 

93LEAFS

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With the exception of Game 2 of the Eastern Conference Final against Tampa Bay in 2011, it's not like Seguin had that much of an impact on the Bruins winning that year. In 2013 when he was no longer a healthy scratch in the playoffs and him playing more of a bigger role, the Bruins lost in the Stanley Cup Final.
It wasn't Seguin that made the difference, but the cap space plus Seguin that helped. If they signed Kessel, they wouldn't have had the cap space to add Nathan Horton. That was a huge finishing piece to that team.
 
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LeafsNation75

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It wasn't Seguin that made the difference, but the cap space plus Seguin that helped. If they signed Kessel, they wouldn't have had the cap space to add Nathan Horton. That was a huge finishing piece to that team.
Thinking back I wonder if the Bruins would have matched an offer sheet if Brian Burke actually offered one to Kessel and he signed it. I remember hearing Peter Chiarelli saying he would do that no matter what and if that happened we can assume Toronto keeps their 2010 1st round pick and selects Seguin 2nd overall.
 

93LEAFS

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Thinking back I wonder if the Bruins would have matched an offer sheet if Brian Burke actually offered one to Kessel and he signed it. I remember hearing Peter Chiarelli saying he would do that no matter what and if that happened we can assume Toronto keeps their 2010 1st round pick and selects Seguin 2nd overall.
Without Kessel, its also realistic to think that Leafs finish below Oilers. Assuming lotto results held, it would be interesting where we went on Tyler vs Taylor. Taylor was the favorite but Tyler had notable support.
 

LeafsNation75

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Without Kessel, its also realistic to think that Leafs finish below Oilers. Assuming lotto results held, it would be interesting where we went on Tyler vs Taylor. Taylor was the favorite but Tyler had notable support.
I remember during that behind the draft 2010 special Brian Burke told Kevin Lowe the Oilers made the right choice. So if the Leafs kept their 1st round pick and got 1st overall that year, that leads me to believe he would have went with Taylor Hall. Of course that season Kessel also missed the first month due to his wrist surgery, so I think at worst they still finish where they did which was 2nd last overall.
 

Craig Button

The C is for Coward - Brad Marchand 2024
Jul 28, 2015
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Atleast Berard turned into Redden who was a good player for you guys.

Well, I can't say you 100% would of. But, assuming the same numbers came up, and the team that finished 31st got the same numbers assigned you would have gotten Dahlin. The 31st place team got Dahlin this year. Obviously, like Back to the Future or a bunch of sci-fi movies, you change one small thing in the past it can alter the present in unforeseen ways.

would've
would have
 

93LEAFS

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I remember during that behind the draft 2010 special Brian Burke told Kevin Lowe the Oilers made the right choice. So if the Leafs kept their 1st round pick and got 1st overall that year, that leads me to believe he would have went with Taylor Hall. Of course that season Kessel also missed the first month due to his wrist surgery, so I think at worst they still finish where they did which was 2nd last overall.
Who knows, but we were tied for last at that point before Phil's return (Phil Returned November 3rd) and 8 points behind the Oilers.
 

Beville

#ForTheBoys
Mar 4, 2011
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Obviously the popular opinion (understatement) is that Doug Wilson and the Sharks fleeced Dorion and the Sens in the Karlsson trade. This got me thinking, how many trades in the past seemed badly one-sided only to flip the other way in the future?
And Boedker for Hoffman, don’t forget.
 

JT Kreider

FIRE GORDIE CLARK
Dec 24, 2010
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At the time I thought CBJ got blown out of the water in the Jones trade. Instead Johansen has stagnated at best and Jones has developed into one of the best defensemen in the league.

Also everyone in hockey thought the Rangers didn't get nearly enough from Tampa for McDonagh. Now in comparison to the Karlsson trade it seems we got the moon and then some for him. Hajek especially as seen his stock skyrocket since the trade and is our prospect outside the big 4.
 
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maacoshark

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Jul 22, 2017
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It wasn't nearly as lopsided, but I remember when Montreal traded John Leclair, Gilbert Dionne, and Eric Desjardins to Philadelphia for Mark Recchi, I distinctly remember people in the media saying that the team that gets the best player wins the trade and hence Montreal won this one. Well it turned out that Leclair was a better player than anyone gave him credit for, and while Recchi is obviously no slouch, he never did for Montreal what Leclair did for the Flyers.
At the time that deal was made I thought Philly got the better of the deal. I still think that.
 

BigBadBruins7708

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Dec 11, 2017
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Yeah I’m sure they would of never got that with Kessel on the team instead of Seguin

actually we wouldn't have.

with Kessel instead of Seguin the Bruins dont have the cap flexibility to make the key trades to acquire Chris Kelly, Peverley and Kaberle.

Kelly and Peverley were essential pieces to the Cup run.

They also dont have the cap space to trade for Horton and Campbell. Horton being their deadliest goal scorer in the playoffs on their best line of Lucic-Krejci-Horton. Campbell centering the best 4th line in hockey with Thornton and Paille.

Without Kelly, Peverley, Horton, Campbell they do not have the depth to win, and are without 4 impact players from the run
 

izzy

go
Apr 29, 2012
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Well, we'll never have the organizational and management strength that you guys have - at least not with current ownership.

But I appreciate the concept. ;)

We've drafted well over the years from time to time, Karlsson was #15, Stone was #178.

But it's hard to be optimistic if we can't hold on to them once they've hit their primes.

Anyway, I don't want to take over another thread with this stuff.

I'd say that Toronto elegantly made the most out of their lopsided deal.

pageau 4th rounder
dzingel 7th rounder
hoffman 5th rounder
 

nbwingsfan

Registered User
Dec 13, 2009
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I’m going to be this guy too.

Kessel for Seguin, Hamilton and knight. 9 years later.

Leafs have to show for it Kapanen, Andersen and Greenway. A top 9 forwar with still decent up side. A starting goalie who some view as a top end starter. A meh prospect that probably won’t equate to much.

Bruins have to show for it Zach Seneshyn, Forsback-Karlsson and Louzon. More time needed but at the moment neither seem like more than top 9 forwards or bottom pairing D at best.

Boston also got a cup, something conveniently left out for reasons unknown...
 

Viqsi

"that chick from Ohio"
Oct 5, 2007
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I remember when it was painfully obvious to all involved that we got absolutely ripped off by the Rangers, giving up star scoring winger Nikolay Zherdev and depth scorer Dan Fritsche for utterly hopeless Christian Backman and unremarkable Fedor Tyutin.
 

Extra Texture

A new career
Mar 21, 2008
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Meh, that's like saying it was a good idea to trade for Matt Duchene because the chemistry of our team tanked and we ended up with really good lottery odds that allowed us to draft Rasmus Dahlin.

Exactly.

If you're going to factor the Leafs getting Matthews as part of the Kessel trade, then almost every big trade in NHL history needs to be reevaluated and recalculated. Picking through the consequences of a trade is usually difficult enough without the butterfly effect of future events.
 

Mick Riddleton

“A day without sunshine is like, you know, night.”
Apr 24, 2017
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Niagara
Cam Neely and a 1st rounder for Barry Pederson. Pederson at the time was the way better player, playing the top centre position with Rick Middleton in the day. Middleton after 2 seasons with the Rangers was acquired for Ken Hodge, that worked out amazingly. Both Hodge and Pederson were the established players of their day and soon faded away for the younger guys.
 

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