Prompt #1

For the Montréal Canadiens, the Scott Gomez VS Ryan Mcdonagh is one of the worst with Mike Ribeiro VS Janne Niinimaa.
For the first one, they wanted to get a playmaker that was able to get at least 70 pts and be a #1 center. Two things that he never was able to be in Montréal and was at one point more than 1 year without scoring a single goal... For him, MTL gave one of their best prospects, a defenseman that had a lot leadership for his age and a first round pick. Not a offensive defenseman in college, but still produced at least 30 pts for half of his career while being a very reliable defenseman in his zone.

The other trade saw a québécois getting trade away for off ice reasons for a player that only played half a season with the team.
Ribeiro had a breaking season (65 pts) before the lookout in 2004 and after another good season, was traded to Dallas, where he had his 3 best seasons in his career (81,78 and 71 pts). After the trade, Ribeiro played 11 seasons in the NHL before major personal problems put a stop to his career. For him, Montréal got a defensive defenseman that his good years were far behind him. Only 3 pts in 41 games in Québec and that was the end of him in the NHL. He played in Swiss and Sweden where he had some success, but the caliber is way bellow to the NHL.

That's the two worst trade in my eyes in the last decade of the Canadiens, where they got completely robbed by the other team.