Adam Smith is often thought to be an unequivocal advocate of capitalism based on unfettered self-interest. Against this caricature, I argue that his attitudes towards commercial society are, in fact, more ambivalent. To ground this claim, I outline Smith’s account of ambition, a passion responsible for the dynamism of commercial economies but deleterious to individual happiness, and focus on the rhetoric Smith deploys in his portraits of three ambitious characters: the poor man’s son, the ambitious man, and the prudent man. Next, I challenge alternative interpretations. In particular, I contest Samuel Fleischacker’s view that Smith no longer sees ambition, motivated by vanity, as the driving force behind economic growth in commercial society by the time he writes the Wealth of Nations and, thus, is not meaningfully ambivalent. In the last section, I draw on recent work by Amelie Rorty to argue that Smith’s ambivalence towards commercial society is both appropriate and constructive.