This paper offers a new framework for thinking about the relationship between the common law of property and the rule of law. The standard way of framing this relationship is within the terms of the form/substance debate within the literature on the rule of law: Does the rule of law include only formal and procedural aspects or does it also encompass and support substantive rights such as private property rights and civil liberties? By focusing on the nature of common-law reasoning, I wish to question the form/substance dichotomy that frames this debate and to show that the formal aspects of the rule of law are in fact principles widely adopted within the practice of common-law reasoning and as such play a large role in shaping the substantive content of common-law property rights. Understanding this has implications beyond the relationship between property law and the rule of law.

This essay investigates the structure of fiduciary obligations, specifically the obligation of loyalty. Fiduciary obligations differ from promissory obligations with respect to the possibility of “accidental compliance.” Promissory obligations can be satisfied through behavior that conforms to a promise, even if that behavior is done for inappropriate reasons. By contrast, fiduciary loyalty necessarily has an intentional dimension, one that prevents satisfaction through accidental compliance. The intentional dimension of fiduciary loyalty is best described by what we call the “shaping” account. This account both explains the conscientiousness that loyalty demands and improves on other accounts of the intentional dimension of loyalty. Our analysis challenges two of the most prominent ways of conceptualizing fiduciary obligations. “Contractarianism” configures fiduciary obligations as a species of contractual duties. The view that we call “proscriptivism” reduces fiduciary obligations to the juridical prohibitions that apply to fiduciaries. Neither of these approaches is satisfactory, because each neglects the intentional dimension of fiduciary loyalty.

Proponents of strict rule-based theories of judicial reasoning in common-law systems have offered a number of criticisms of analogical alternatives. I explain these criticisms and show that at best they apply equally well to rule-based theories. Further, I show how the analogical theories explain a feature of judicial common-law reasoning—the practice of distinguishing cases—that rule-based theories ignore. Finally, I show that reason-based, analogical theories of common-law judicial reasoning, such as those offered by John Horty and Grant Lamond, offer especially strong rejoinders to the rule-theorist objections and persuasive accounts of distinguishing.