If Serendip is considered both the place and the metaphoric space in which fortuitous events occur, Zembla is its opposite (Boyd, 1998). Moving from the concept of managerial serendipity (Cunha et al., 2015), we posit that the world-known sinking of the sinking of Costa Concordia is a case of managerial zemblanity, in which an excess of self-confidence, an absence of generative doubt, the presence of (delusional) managerial control, a vicious dynamic of organizational legitimacy and an insufficiency of organization design (Heeks & Bhatnagar, 2001) explain a catastrophic outcome (organizational performance). There is an abundant literature that implies the need for research into a lack (or absence) of organizational “wisdom” (e.g. ten Bos, 2007) or “smartness” (e.g. Alvesson & Spicer, 2012). In this paper we will theorize the under-researched process of zemblanity in order to understand how organizations sometimes create disasters that were avoidable, accidents that in systems regarded as “high reliability” should not have occurred. The Costa Concordia provides a case of organizational zemblanity in which both active and passive behaviours by the Captain created a vicious circle of bad decisions (Masuch, 1985), complemented by structural elements found both in the individual behaviours of others (mainly, the vessel’s first line of command) and the lack of other effective organizational controls, in terms of structures and routines.