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In June 2007, the Supreme Court of Canada expressly overruled 20 years of jurisprudence that interpreted the freedom of association as excluding collective bargaining. This about-face by the Supreme Court was unexpected. What gave rise to this remarkable decision and what does it portend for the role of the courts in labour relations in Canada and beyond? The recent successes before courts have led some observers to suggest that it may now be a propitious time for a coordinated and proactive litigation strategy to vindicate labour's collective rights. This article offers some preliminary answers to these broader questions and issues by focussing on the Supreme Court's decision in the Health Services and Support case.