Abstract: In recent decades there has been a growing interest in the issue of overall freedom-measurement. Consequently, two competing approaches to this issue have emerged: an evaluative approach and an empirical (non-evaluative) approach. Advocates of both approaches agree that one of the most important challenges that they have to meet consists in accommodating the judgement that, all other things being equal, the more diverse a set of freedom is, the more overall freedom it offers us. The diversity of one’s freedoms seems to depend, however, on the degree to which they are significantly different from one another, and the notion of significant difference is a value-based notion. Hence, it seems that, unlike the evaluative approach, the empirical approach cannot meet this challenge. This claim has been contested, though, by Ian Carter. In his seminal book A measure of freedom he argues that his empirical theory of overall freedom-measurement manages to accommodate the aforementioned judgement about freedom and diversity as effectively as any evaluative theory, and shows, moreover, why the evaluative way of dealing with this issue in general is misguided. In this article I argue that, as a matter of fact, it is Carter’s non-evaluative theory of freedom and diversity that is misguided, as it cannot properly accommodate the aforementioned judgement about freedom and diversity. If my argument is sound, then it would not only undermine Carter’s theory of freedom and diversity. It would also cast a very serious doubt on the empirical approach to overall freedom-measurement in general.