This thesis examines and critiques attempts by researchers in the field of artificial intelligence and law to simulate legal analogical reasoning. Supported by an analysis of legal theoretical accounts of legal analogising, and an examination of approaches to simulating analogising developed in the field of artificial intelligence, it is argued that simulations of legal analogising fall far short of simulating all the is involved in human analogising. These examinations of legal theory and artificial intelligence inform a detailed critique of simulations of legal analogising. It is argued that simulations of legal analogising are limited in the kind of legal analogising they can simulate - these simulations cannot simulate the semantic flexibility that is characteristic of creative analogising. This thesis argues that one reason for current restrictions on simulations of legal analogising is that researchers in artificial intelligence and law have ignored the important role played by legal principles in legal analogising. It is argued that improvements in simulations of legal analogising will come from incorporating the influence of legal principles on legal analogising and that until researchers address this semantic flexibility and the role that legal principles play in generating it, simulations of legal analogising will be restricted and of benefit only for limited uses and in restricted areas of the law. Building on the analysis of legal theoretical accounts of legal reasoning and the examination of the processes of analogising, this thesis further argues that legal theoretical accounts of legal analogising are insufficient to account for legal analogising. This thesis argues that legal theorists have themselves ignored important aspects of legal analogising and hence that legal theoretical accounts of legal analogising are deficient. This thesis offers suggestions as to some of the modifications required in legal theory in order to better account for the processes of legal analogising
