The doctrine of regulatory or constructive taking establishes limits on the public regulation of private property in much of the common law world. When public regulation becomes unduly onerous — so as, in effect, to take a property interest from a private owner — the public will be required to compensate the owner for its loss. In 2000, the City of Vancouver passed a by-law that limited the use of a century-old rail line to a public thoroughfare. The Canadian Pacific Railway, which owned the line, claimed the regulation amounted to a taking of its property for which the city should pay compensation. The case, which rose to the Supreme Court of Canada in 2006, marked that court’s first engagement with the doctrine of regulatory taking (also known in Canada as de facto expropriation) in nearly twenty years. This chapter explores the intertwined histories of a railway company and a city that gave rise to CPR v. City of Vancouver. It then analyzes the court decisions and considers the role of courts in mediating the appropriate boundary between private property and public regulation in a jurisdiction where there is no constitutional protection for private property.