This chapter begins with a discussion of Neil MacCormick’s institutionalist approach to legal phenomena, and argues that this theoretical framework has value as a way to study multiple offense sentencing (MOS). The most thorough completed empirical research into MOS, by Austin Lovegrove in Victoria, Australia, is then considered, alongside the leading Victorian case of Azzopardi v. R. Congruently with the expectations of institutionalism, this analysis uncovers several separate normative principles used by judges in MOS practice. These results are discussed through the lens of what can be described as “post-desert theory.” Overall, the analyses in the chapter are intended to pave the way for the development of a more coherent answer to the question: “what principles should optimally guide sentencers when dealing with cases involving multiple offenses?”