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(1) Mark Recchi

Not only was Recchi involved in two of the worst trades in Habs history, he also turned into the biggest asshat to wear a Bruins jersey since...well, there are a lot of asshats that have worn that jersey.
Forgetting that Dr. David Mulder helped save his good friend Saku Koivu's life, Recchi actually questioned whether or not one of the most respected doctors in the world was honest in his diagnosis of Pacioretty.
Some will say that he was just deflecting the attention away from the goon known as Zdeno Chara, but let's be honest, a captain shouldn't need someone to take the heat for his own actions. Either Chara is a terrible leader, or Recchi was full of crap.
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(4) Benoit Pouliot

Bambi signed with the Bruins following their victory of the Habs in the 2011 playoffs. Essentially he established that he's a front runner that will switch allegiances at the drop of the hat.
Bambidict Arnold, as he's known around Montreal, failed to find any success with the Bruins, and enjoyed a first round elimination in 2012.
This should be an easy win for Dr. Recchi, but let's see how the votes go. Bambi might have an outside shot at an underdog victory.