Trades in which a player traded from a desirable/successful organization to the opposite?

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Yes it was mostly the second seaso/Neilson n when it went really bad relation wise, he was benched some games, played 0 minutes of the 1998 playoff and was asked to cut sticks during practice (according to Daigle).

Maybe his career ending is more graceful if he do not request that trade after all.

The Whalers-Cane when he went back there, were making the playoff by 1999 and he got to play 23 minutes a night during them....

40 points in 69 games as a 38 year old defenseman. Not bad. Played in the playoffs too. He obviously wasn't "Coffey" anymore, and his defense left a lot to be desired at that point but that is probably the only decent year post-1996 he had. But even in Philly he wasn't used properly and should have been better. He did get an injury his first year there, maybe that sort of partially had him throw in the towel, I don't know, but that is strange that he wasn't used at all in the playoffs in 1998. And it makes sense why Wayne Cashman never coached in another season in the NHL other than that one. I just wonder how much of Coffey's passion got destroyed after the 1996 trade. This guy is 5th in Norris voting in 1996. He still has some left in the tank. I've never heard him speak about it. I guess he doesn't have to, he did plenty in his career.
 
Maybe doesn't exactly fit, but Bill Guerin relayed a funny story during a Spittin' Chiclets podcast. He was a contract holdout to begin the 1997-98 season and requested a trade. He eventually signed (in order to get in shape for the 1998 Olympics) but didn't rescind the trade demand. Later he'd be traded with Valeri Zelepukin to Edmonton for Jason Arnott and Bryan Muir.

He was sitting next to Zelepukin on the plane ride to Edmonton. According to Guerin, Zelepukin didn't say a single word the entire flight but as soon as they landed he said something like "God dammit Billy, you had to ask for a trade."

At that point Edmonton made the playoffs in 1997 and 1998, but in those days 8 of the 13 West teams would qualify and there were a couple bad squads. Devils had been the #1 seed in 1997 and were set to do the same in 1998. Guerin said he enjoyed his time in Edmonton. Zelepukin would finish that season with the Oilers before being shipped out to Philadelphia.

Edit: Looks like Zelepukin extended with Edmonton in late July 1998, but was traded to Philly in early October 1998. Oddly it looks like they left Zelepukin exposed in the old waiver draft but he wasn't taken. But I think the old rules required you to expose somebody if you picked a player up.

Edit #2: Looked up the Guerin/Zelepukin story for the lolz:

 
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Marc Andre Fleury going from the cup winning Penguins to the expansion Knights who were expected to be a terrible team.
And then of course being traded by VGK immediately after a Vezina and Jennings-winning season to the crumbling ruins of the Chicago Blackhawks, who would finish with 68 pts that year
 
the one that comes to mind is ray sheppard from detroit (presidents trophy) to san jose (coming off a couple goodish seasons but destined to finish 2nd last) to get igor larionov, who shone against the wings the last two playoffs. this was the fall of 1995, coming off the new jersey finals sweep.

but then ray got the first laugh, getting traded to florida at the deadline and beating his old team to the finals.
 
Man, I read this six times before I realized it says "to the finals" and not "in the finals".

haha, sorry for the false alarm, avs fan.

but things makes me wonder, is ray sheppard the only person to ever be swept in the finals in back to back years by different teams, and on different teams?

also, just tuning in to tonight’s game, heading into the third. can’t complain about the score so far ;)
 
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I remember it
He had a cup of coffee (no pun intended) with the Blackhawks and Bruins towards the end and it was not pretty. After he left the Red Wings in 96, he was a fringe PP specialist at best. He did have a decent final full season with Carolina, but was done by the next season and lasted 18 games with the Bruins. I thought he'd be the one to put the Flyers over the top in 96-97 but was proven wrong, as he wasn't a factor in the playoffs (though he did well with Philly in the regular season).
 
Tyler Johnson getting traded from the 2 time Stanley Cup Champs TB Lightning to the God-awful Chicago Blackhawks.
Kind of funny that at one point he was considered the most talented out of the Johnson-Palat-Kucherov trio with Kucherov being the expendable one. Now 10 years later Johnson is basically done, while Kucherov is in contention for the Art Ross every year.
 
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Esposito traded from Boston to the declining Rangers was another example too. Although Esposito still had some good years left in him, and he certainly made the best out of it.

Doug Weight getting traded to Edmonton from the Rangers for Tikkanen. He went to a dumpster fire and left a team that would famously win that year.

I guess we'll say the most obvious one - Gretzky in 1988.
Espo hated the trade but Jacobs hated a trust he had with the team that he refused to revoke hence the trade.

I still hate the Weight trade,Tikkanen was obviously a huge part of the cup win but he wasn't worth Weight. Doug Weight on those post 94 Ranger teams could have been the difference in winning another cup.
 
Esposito traded from Boston to the declining Rangers was another example too. Although Esposito still had some good years left in him, and he certainly made the best out of it.

Espo was in the Finals with the Rangers three years after the trade, so I'm not sure it qualifies as going from a great team to a mess.

The end of Coffey's career just seems ridiculous. Like, he played for who those last few years...? Boston, I think? Carolina? Does anyone even remember this?

Chicago.
 
You could make the argument that Jimmy Carson being traded to the defending Stanley Cup champion Oilers in 1988 was a bad move for him individually. Started his career with almost historically great numbers with L.A. and then was a bad fit in Edmonton and never really recovered.

He might have been a bad fit in Edmonton, but he had a fantastic season there. He scored 49 goals and had 100 points the year after the trade.
 
Coffey missed the final two Cup final games in Detroit. Other than that he played every playoff game. It didn't make a difference, Philly was even worse in Game 3 without him and then lost Game 4 too. Coffey didn't play well in Games 1 and 2, but he wasn't the problem. Remember, it was Terry Murray, not Roger Neilson, as coach of the Flyers that season. I honestly don't know why they traded Dino. They got nothing back for him. Eventually they got lucky and Holmstrom played Dino's role, but he wasn't used really in 1997. By 1998 he had a good playoff though. But I think they win the Cup in 1997 with Dino. I am not sure if they do without Shanahan though and instead have an older Coffey and a playoff no-show in Primeau. So that was a good trade in reality. But sucks to be Coffey. However he had nothing left to prove with that career, plenty of championships too.

Wings traded Dino because of the waiver draft which Bowman publicly explained at the time. Same reason they traded Vernon btw (+money).
 
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I always felt bad for Blake Wheeler who missed the Bruins' cup run because he got traded to the moribund Atlanta Thrashers in their final season at the deadline
 
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Lewis and Harris (Isles first ever draft pick) going from the Isles to the Kings for Goring a couple of months before their dynasty began.

Chico Resch going from the Isles to the Devils one year into the dynasty. Still burns me the habs traded for Herron instead of going after the available Resch. Would have been a great stop gap between the Dryden and Roy eras.

These guys are always who I think of when this topic comes up.

Lewis and Harris basically were with the Isles for their entire build-up to a dynasty and then got traded 2 months before the team went on to win 19 straight playoff series. I don't think there's anything that comes close to it in terms of 'hard luck trades' for a player in NHL history.

Gerry Hart was also an original Islander who was lost in the 1979 Expansion Draft to Quebec so he met a quite similar fate, just slightly sooner.
 
The end of Coffey's career just seems ridiculous. Like, he played for who those last few years...? Boston, I think? Carolina? Does anyone even remember this?

I hated to see that happen to him. I loved him as a player. But at the end he didn't have the wheels to be as effective offensively and he was just not good defensively. he played for so many teams at the end - Carolina, Boston, Chicago, Philly...
 
In the 1950s and 1960s, the New York Rangers were a team which rarely made the playoffs - and never won a series. During this period, you had Red Kelly threaten to quit hockey when he was traded to the Rangers. You had Jacques Plante, Phil Goyette and Don Marshall - with all their Stanley Cup rings - traded to New York. You also had Dick Duff and Bob Nevin - who had just won two Cups in Toronto - headed to the Rangers. Recalling that trade, Andy Bathgate said it must have been "culture shock" going from the cup-hoisting Leafs to New York - where the circus trumped the Rangers.
 
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Ice Hockey Wiki has an image* of Ron Stewart on the Boston Bruins' bench - with rookie Bobby Orr seated beside him. The 1966-67 season was Stewart's second with the Bruins. Punch Imlach traded Ron to Boston after the 1964-65 season. In Toronto, Stewart had gone to the Stanley Cup Final five times, and hoisted the trophy three times. The Bruins - going in to the 1965-66 season - had missed the playoffs six straight seasons. They did it again in 1965-66 and in 1966-67. Orr's rookie season, Boston won just 17 of their 70 games. Their 44 points left them in last place, 14 points behind the fifth place Detroit Red Wings.

If you can find that image, check out the expression on Ron Stewart's face. Almost as good is the expression on his face in the team photo for 1966-67.

(* which - for some reason - I am unable to post below)
 

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