William Boyd (1998) coined the term zemblanity as the antonym of serendipity by referring to a physical space (Zembla) conceived as the opposite of Serendip. Zemblanity is the exact opposite of serendipity, referring to the making of unhappy, unlucky discoveries by design. Moving from the concept of managerial serendipity (Cunha et al. 2015), we posit that the world-known sinking of the 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 (e.g. Ciborra & Lanzara, 1994), 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 avoidable disasters, even in systems regarded as “high reliability”.