(2) Claude Julien
Born as Guillaume Fontaine de la Tour D'Haute Rive, Claude quickly changed his name to Julien as to command more respect in hockey circles and escape his previous arrests for disorderly conduct at a buffet.
After being fired by the Habs in 2005, and consequently by the Devils in the following year, Julien found a job with the lowly Bruins. He managed a to do wonders with the club, with his enforcement of the Diveastroika ideology. This plan to embellish not only ensured he kept his job, but brought Boston a Stanley Cup. He also won the award for the most see through whining in the history of hockey. Keep up the great work Guillaume!
(3) Michael Ryder
The master floater is best known for his save in the 2011 playoffs versus the Canadiens, which was actually the first time in his entire career that he back checked.
Although he put up better numbers with the Habs than with the Bruins, Ryder floated his way to getting his name engraved on the Stanley Cup, thus ensuring he would be known as a Habs traitor forever more.
There were plans to ask Ryder about his traitorous career at the end of the 2013 season, but unfortunately he escaped interrogation, and fled the scene. A classic traitor move.