In Plato' s early dialogues (Meno, Laches, Protagoras and elsewhere) there are many paradoxical positions attributed to Socrates that are associated with his moral theory. These are not strictly paradoxes in the philosophical sense but rather in the literal sense being statements that run counter (para) to common opinion (doxa). The phenomenon of akrasia or weakness of will is discussed most explicitly in the Protagoras. There Socrates argues that no one willingly does anything but what is best. Elsewhere (notably in the Gorgias) Socrates argues that what is best for us is to do what is right. It follows that no one willingly does wrong. There is further discussion of these doctrines in relation to the phenomenon of the weakness of will in Plato' s middle and latter dialogues (Republic, Laws). Most scholars attribute these paradoxical state¬ments to Socrates and not to Plato. Indeed, it seems that Plato differentiates his position from Socrates accepting some possibility of the existence of the weakness of will in the Laws. Aristotle in the Nicomachean Ethics (Book, VII) discusses akrasia with reference to the Socratic position complaining that Socrates contradicts the appearances (ta phenomena). This paper discusses these different positions in classical moral theory (Socratic, Platonic and Aristotelian) on akrasia, as they have been analyzed and interpreted by various contemporary ancient philosophy scholars, and examines them in relation to each other, bringing together under a new perspective the three philosophers, and in relation to contemporary theories on the weakness of will. It is argued that further research needs to be done in this direction via a thorough and detailed examination of these three classical moral doctrines on akrasia, and their interrelation, that could throw new light on the puzzle of weakness of will.