The legal regulatory regimes for communication technologies evolve with technological, economic, and social change. This paper asserts that, in the United States, the evolution of the legal regulatory regimes for the communications sector is following a trajectory breathtakingly similar to that already traversed by the transportation sector. As both sectors provide infrastructures essential to the nation and share similar economic attributes of networks, technological evolution within each has generated many of the same core issues. By recognizing this historical reality, we can tap valuable experience in transportation policy to better inform prospective policy change in communications. In this way, future communications policy need not be radical—whether intentionally or unintentionally—nor totally untested, thereby enhancing its potential for sustainability.