Only naming off 90s-00s trades cause I don't want to name off the past trades I wasn't alive for...so I'll name off the ones I do remember, which are the few memorable and happy trades the habs made and then the many bad trades the habs made...
Best trades:
1) Robert
Picard for Winnipegs 3rd round pick (
Patrick Roy)
2) Shayne
Corson + Brent Gilchrist for Edmonton's
Vincent Damphousse
3) Craig
Rivet for San Jose's
Josh Gorges + 1st round pick (
Max Pacioretty)
4) Josef
Balej for NYR's
Alexei Kovalev
Worst trades:
1)
Patrick Roy + Mike Keane for Colorado's Jocelyn Thibault + Martin Rucinsky + Andrei Kovalenko
2)
Pierre Turgeon + Craig Conroy for St Louis' Shayne Corson + Murra Baron + 5th round
3)
Chris Chelios for Chicago's
declining Denis Savard
4)
Vincent Damphousse for San Jose's 1st, 2nd and 5th round picks that turned into 2 nobodies and
Marcel Hossa
5)
Ryan Mcdonagh + Chris Higgins for NYR's
Scott Gomez
6)
Mike Ribeiro for Dallas' Janne Niinimaa