Most people will probably pick the Kaberle deal. Not me.
No.1 by a bullet is the Cammalleri trade. Cammy is a legitimate 1st-line winger (or centreman!), a bona-fide sniper, and our top playoff scorer two seasons running. So of course we traded him for a slug, then put the cap savings to no good use. Swell. Whatever you think about Cammalleri, we should have gotten a far better return for the only veteran on our roster that anybody considered a 'star.' Habs29 was dead right about Bourque, unfortunately.
No.2 is the Lapierre trade. We basically threw away a player who, when on his game, is possibly the best 4th-line C in hockey, and a superb agitator to boot. This, in an era when we cycled through fourth-liners like used condoms, desperately scrambling year after year to plug gaping holes in the bottom six. So basically we threw away the solution to the problem we spent the next year and half trying to fix.
I am still peeved that he did not even approach Wisniewski about possibly staying here. I mean, the absence of a Markov replacement was THE biggest reason for the collapse last season.
The real issue with Gauthier, though, wasn't bad deals - though they didn't help - so much as confused and toxic leadership that poisoned the organizational culture.