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

[IslesFan2017]

The other day, I was reading about Chris Terreri on here and it reminded me of him being traded by the Devils to the Islanders for John Vanbiesbrouck before the trade deadline in the 2000-01 season. Even though I don't remember the exact details, I remember reading in "Fish Sticks: The Fall and Rise of the New York Islanders" that he was disappointed and unhappy being sent to the Islanders. At least Terreri didn't have to move very far from New Jersey to Long Island.

The Devils were the defending champions and on their way back to the Finals before losing Game 7 to the Avalanche. On the other hand, the Islanders had been one of the worse teams in the league since the mid-1990s and had suffered from ownership issues off-the-ice. Nassau Coliseum was already outdated and that only added to the miserable atmosphere surrounding the Islanders at the time. The Islanders finished in 30th place that season although if I recall from the book, there was some optimism for the Islanders before that season due to increased payroll.

I couldn't find much about the trade except this ESPN article: ESPN.com - NHL - Devils deal veteran Terreri in goalie swap

Do you know of any other similar trades where a player was traded from a successful organization to such a dysfunctional and terribly-run organization?

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[carjackmalone]

During a brief competitive level in the late 70’s Lanny McDonald went from the leafs to cellar dwellers Colorado Rockies

 

[rnhaas]

During a brief competitive level in the late 70’s Lanny McDonald went from the leafs to cellar dwellers Colorado Rockies

Also the Sittler trade from the Flyers. Yes, the Red Wings had finally made the playoffs but only because it was the '80s.

 

[Crosby2010]

Immediately I am thinking about the Coffey trade from Detroit to Hartford. That was just awful. Coffey immediately asked to be traded away and he was traded to Philly two months later. But he got in a collision with John Leclair (in practice I think?) and I don't think he was ever the same. He just might have lost his passion after the Wings traded him in 1996. The last greatness we saw of Coffey was that season and the World Cup, where he played well. From 1996-'01 Coffey was never Coffey again. It reminds me of Messier pretty much post 1997. You want to forget all of those years and they don't matter really in the grand scheme of things. To his credit, Coffey along with Primeau fetched Shanahan in that trade and Shanny was the final piece (along with Larry Murphy later) to the Wings winning.

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.

 

[vadim sharifijanov]

i always wondered if when lou was trading away guys who wanted too much money, whether he did them dirty on purpose, sending them to bad teams/dysfunctional orgs.

verbeek and sean burke were both traded to hartford

and i’m not sure if he was a salary negotiations purge or they were just making room for fetisov/kasatonov but kurvers was traded to toronto near the end of the pre-fletcher years

but i imagine being john maclean in the early 90s looking at all his former teammates while he’s scoring 40 goals a year and being careful to never step out of line

 

[MadLuke]

Like Coffey, Ciccarelli went from the the team that would win the next 2 cups (detroit) to Tampa Bay in the summer of 1996, than the other florida team the panthers, never played a playoff game again.

Still did really well (35 goals and an all star game appearance in 1997)

asked to be traded away and he was traded to Philly two months later.

with how he was treated there by Neilson (including not playing in the playoff) and benched some games in the end of the regular seasons...