<p>Argument interpretation and reconstruction are two necessary presuppositions of argument analysis and evaluation, constituting a cornerstone of argumentation theory. One of the most used, and at the same time most controversial, principles underlying this interpretative practice is the Principle of Charity (CP), recommending a “charitable” (i.e., the strongest, or a strong within certain limits) reconstruction of the arguments expressed in a text. Grounded on “ethical,” “practical,” or “strategic” considerations, criticized, rejected, or replaced by criteria seen as inherently charitable, the various versions of CP advanced in argumentation theory raise the basic questions of where charity comes from, and how in the history of argumentation the problem of argument reconstruction was addressed before the concept of charity. This paper aims to provide a historical overview of the Charity Principles, evaluating them in light of some challenging cases. Such accounts will be compared with the Aristotelian principles used for reconstructing enthymematic arguments, which can be regarded as the predecessors of the modern CP. The Aristotelian texts suggest hermeneutic and logical guidelines grounded on the pragmatic and dialectical dimensions of rhetorical arguments, which avoid some pitfalls of charity and complement some fundamental insights of the CP tradition.</p>