This paper forms part of a collection in honour of a special jurist and, as such, it addresses themes both general and particular. While focused on a judge whose influence on the evolution of Charter doctrine between 1989 and 1999 may be unequalled, it also examines the dilemmas the Supreme Court faced as it implemented the early landmarks. If those precedents imposed constraints, the Court of Cory J.'s era exercised enormous power in shaping a jurisprudence of its own. This paper examines the relationship between two generations of interpretation from the perspective of a distinctive jurist, Peter de Carteret Cory.