This paper examines the ‘fact-value separation’ in the context of the practice of legal theory, legal scholarship and legal reasoning. It is divided into three parts: the first part examines recent prominent attempts to move beyond the fact-value dichotomy, while retaining the explanatory utility of the distinction between facts and values; the second analyses the role of the separation in the context of Neil MacCormick’s methodological reflections on the practice of legal theory and legal scholarship; and the third considers the role of the separation in the context of MacCormick’s theory of legal reasoning. The paper argues that although reference to thick terms or thick concepts does help to see the entanglement of facts and values, a better strategy for resisting the dichotomy (while not destroying the utility of the distinction) is to focus on the processes involved in the evaluative lives of evaluative beings (as recommended recently by Andrew Sayer in his Why Things Matter to People, 2011). One of the key features of this evaluative life is (in Sayer’s words) our active ‘striving across the gap between what we have and what we could be, or need or want to be.’ The paper examines the evaluative life of legal theorists, legal scholars and legal practitioners (particularly as this is depicted by MacCormick), and thereby seeks to point to the entanglement of fact and value in the practice of legal theory, legal scholarship and legal reasoning.