Studies of futurity typically privilege licit economies and assume that the lines between licit and illicit institutions are largely clear to the actors involved. But what happens to those actors, and their grip on the future, when such lines blur? This article explores the epistemic crossroads of futurity and legality by focusing on ambiguity. From 1986 to 2009, the Stanford Financial Group reaped billions of dollars selling fraudulent investment products to thousands of Venezuelans. During this span, Venezuelans suffered successive governments’ shambolic currency schemes, bureaucratic dysfunction, judicial corruption, political upheaval, and worsening street crime. As crises became routinized, middle-class Venezuelans faced “normative ambiguity,” a loss of familiar legal and moral certainties, undercutting their sense of futurity. Drawing on 54 interviews with defrauded investors and others linked to the case, this article shows how such ambiguity left investors vulnerable to a fraud that promised to restore that threatened futurity.