As governments and legal systems attempt to address the adoption of new technologies of any kind, digital objects included, the development of law is often overlooked. More often than not, law plays a catch-up game, responding to change once it has happened and, far too often, once it is too late for the law to manage challenges that may emerge. It is important, then, that a legal system consider, to the extent possible, challenges posed by new technologies before they occur, and that it be ready to respond to them with innovative solutions. Here we identify just one aspect of necessary legal change, what we call the private law question. How, when forced to answer, will the private law respond to the changes being wrought by the emergence of digital assets and so ensure that it progresses logically and efficiently? The private law question is easily demonstrated by reference to two major classifications of private law: property and contract. The former asks when the law will recognise and enforce rights and entitlements concerning novel digital assets. The latter asks how the law of contract, which facilitates legal exchanges and imposes a mandatory minimum threshold of ‘legal sufficiency’, sees value in digital assets. In suggesting how these questions might be answered, this chapter contains three Parts. The first two summarise the core responses to both the property question and the contract question. The third draws two conclusions that follow from the analysis: (i) that what we see revealed in the emphasis, both in law and scholarship, on the property question is a legal form of the Matthew Effect—that the focus on one question necessarily impoverishes the development of answers to other important questions about the legal response to digital assets. And, (ii), we suggest that the answer to this legal Matthew Effect is to see the questions that we might ask—property, contract, and so forth—not as discrete questions, but as components of a larger, more holistic approach to law which, we argue, is contained within the concept of private law.