What is a trustee and how should we understand her duties? The existing literature typically identifies the trustee in the role of agent, partner or contracting party. This Article re-envisions the trustee in the role of the legal system’s most trusted type of decision-maker: the common law judge. Rather than argue for a top-down recreation of the trustee’s role, this Article contends that valuable lessons can be learned by reconceptualizing how trustees, settlors, and beneficiaries view themselves and each other. Using traditional literature about great judging as a touchstone, the Article argues that those qualities essential to principled adjudication — including candor, competence, integrity, and impartiality — offer fresh insights for trust creation and administration and shed light on certain internal trust governance dilemmas. The Article’s normative claim is that analogizing trustees to judicial surrogates — arbiters, interpreters, problem-solvers, mediators, and communicators — will provide a way to build greater confidence in what might be called a trust community that originates with the settlor but is perpetuated by the trustee and beneficiaries as they function in the lived world.