This Article addresses how courts failed to adequately supervise employers administering pension plans before ERISA. Relying on a number of different legal theories — from an initial theory that pensions were gratuities offered by employers to the recognition that pension promises could create contractual rights — the courts repeatedly found ways to allow employers to promise much and provide little to workers expecting retirement security. In Section III, this Article addresses how Congress failed to create an effective structure for strong bureaucratic enforcement and the bureaucratic agencies with enforcement responsibilities failed to fulfill those functions. Finally, in Section IV, this Article discusses how the courts abdicated their duty to supervise ERISA fiduciaries once bureaucratic failings made ERISA’s private litigation remedy and the supervisory function of the courts increasingly important.