For just over 10 years — from late 1997 to the middle of 2008 — Justice Michel Bastarache played an active role in Charter decision-making at the Supreme Court of Canada. This paper considers his contributions to the Court’s fundamental freedoms jurisprudence, with particular reference to freedom of expression and freedom of association. His decisions on these issues are difficult to reconcile, and it seems that Justice Bastarache changed his approach to both guarantees in a relatively short period of time. The paper asks whether his majority opinions on expressive and associational freedom are examples of principled decision-making or instead should be understood as outcome-oriented in nature.