Disallowance of free speech and equitable speech exchange is apparent in not merely silence where one would normally have an expectation of speech, but also a very particular type of language use on those occasions when speech is ventured. I want to draw attention to one aspect of this veiled way of speaking, what I will refer to as a corrupted use of the speech act of assertion. The felicitously made assertive depends in a very fundamental way on the right to free speech. This is because it conforms to a contract between speaker and addressee, which not only respects free speech but, more importantly, requires it. It is a contract realized in the form of certain felicity conditions (Searle, 1969) which are all in one way or another reflexes of the free speech requirement. In this paper, I will show the ways in which assertion becomes compromised in response to the absence of free speech and equity in speech exchange. I will show, in particular, that certain felicity conditions are violated under these circumstances and that this violation generates an implicature about the speaker’s power or powerlessness. I will suggest, in addition, that these implicated statements on power or powerlessness also serve as discursive expressions of marked affect and speaker identity, born out of the linguistic and broader social inequity within which the speaker functions, and effective, therefore, in laying bare an undemocratic and oppressive social order. The findings of this study are based on a close assessment of dialogue from Orwell’s “Nineteen Eighty Four”.