This paper explores, through illustrations from the law of contract, the important central theme to the effect that the rules and principles, which constitute the doctrine of the law, are not ends in themselves but are, rather, the means through which the courts arrive at substantively fair outcomes in the cases before them. The paper focuses on the concept of ‘radicalism’, which relates to the point at which the courts decide that it is legally permissible to hold that a contract should come to an end because a radical or fundamental ‘legal tipping point’ has not only been arrived at but has, in fact, been crossed. It explores the role of this concept as embodied in the doctrines of frustration, common mistake, discharge by breach, as well as fundamental breach in the context of exception clauses – in particular, how ‘radicalism’ with regard to these doctrines can be viewed from the (integrated) perspectives of structure, linkage and fairness. The paper also touches briefly on linkages amongst the doctrines of economic duress, undue influence and unconscionability, as well as the ultimate aim these doctrines share of achieving fair outcomes in the cases concerned.