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

[Crosby2010]

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.

 

[Brodeur]

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.

 

[Nogatco Rd]

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