Abstract‘The corruption of man is followed by the corruption of language’ (Emerson, Nature and Selected Essays. Ziff, L. (ed.). London: Penguin Classics, 2003, p. 51). Corruption of language is our target. Sounding ambiguity in crisis writings versus fictions, we use tools that signal shades of meaning that allow for alternative reading. From Empson (Seven Types of Ambiguity. London: Random House, 2004) seven types of ambiguity, we scouted and built out four we could set up in digital format: (1) vagueness, (2) contronyms, (3) polysemous words, and (4) unusual juxtapositions of words in rum sequences. We feed these markers of ambiguity on a computer-aided text analysis build-out to trace how ambiguity in leaders’ cant changes with time. We marshaled speeches by President Putin and NATO Secretary Rasmussen (Ukrainian crisis), President Medvedev and President Saakashvili (Russian intervention in Georgia), and speeches by President Saddam Hussein. Novels completed the corpus, Henry James’ The Bostonians, and Flaubert’s Sentimental Education and its original French version, L’Éducation Sentimentale. We suspect ambiguity to be diversely at work in each of these data sets. The four markers of ambiguity increase over time in Putin, Saakashvili, and Hussein; they decrease in NATO, Medvedev, and in James and Flaubert. Across the samples, correlations between the four markers are high and significant.