This dissertation explores Green’s theory of freedom, it discusses where it sits in the contemporary debate on the nature of freedom, and what it contributes to it. I argue that Green presents us with a nuanced notion of freedom, informed by his robust concept of the will and the good. The dissertation discusses Green’s critique of hedonistic naturalism and his appropriation of the Kantian notion of the will, as a vehicle to articulate a notion of the personal good and self-realisation that is distinct from the utilitarian notion of happiness. It critically assesses these ideas and explains why they are important to understand Green’s theory of freedom. Against a backdrop of dichotomies and warring camps, Green provides a refreshing example of a thinker who refuses to side with one fraction or the other. This dissertation therefore presents Green as a philosopher who cannot be easily pigeonholed. It defends him against the accusation that his theory of freedom could provide the ideological underpinnings for totalitarianism by arguing that this charge is the result of the rigid and unhelpful dichotomy between negative and positive freedom, that has unfortunately provided the backdrop for most discussions on the nature of freedom in the contemporary debate. Green’s theory of freedom is applied to contemporary issues such as the struggles of the Trans community and the spread of misinformation to demonstrate its enduring relevance.