This Article explores the role that “regulatory contrarians” can play in promoting more adaptive financial regulation. Such contrarians have several distinguishing features. First, they possess persuasive authority by virtue of their position, access to media and officials, or speaking engagements and reports. Second, they are affiliated with, and enjoy privileged access to, a regulatory entity but are nonetheless independent, as reflected in their budget, staffing, and/or priorities. Finally, they are tasked with studying the regulatory process, policy positions, and the regulated market and in some way reporting on deficiencies and potential improvements. The Article argues that regulatory contrarians can modestly limit the risk that regulators will fail to adapt to newly emerging and ever-shifting financial risks, by either failing to enact new rules or failing to modify or repeal old rules. Despite this potential, the Article argues that, in the domain of financial regulation, contrarians are used only in a small subset of the instances where they can provide value. Currently, financial regulatory contrarians fit into four basic categories: (1) Ombudsman Contrarians, (2) Consumer Representative Contrarians, (3) Investigative Contrarians, and (4) Research Contrarians. Whereas the first two types of contrarians are limited in their subject area to consumer protection and services, the latter two types of contrarians are limited in their methodological scope. Finally, the Article argues that the Dodd-Frank Act holds the potential to improve financial regulation by transcending historical limitations embedded in the traditional categories of financial regulatory contrarians.