While there is a central assumption that charities can be key implementers of Big Society ideals, this paper will consider whether there is compatibility between the political rhetoric of the Big Society and its delivery through the charitable sector. It will be maintained that, while much obvious synergy exists, there are inherent difficulties, at both the practical and theoretical level, for the large-scale involvement of charities and their volunteers in the delivery of the Big Society. At the practical level, it will be seen that some amendments to the legal framework, so as to accommodate the greater use of charities and volunteers within the Big Society, may need to be brought into effect. However, at the foundational level, an examination of the core characteristics of charities and their substantive legal principles reveals some more fundamental impediments to their fulfilling Big Society objectives laid out for them by government.