A standing presumption in the literature is that devil’s advocacy is an inherently beneficial argumentative move; and that those who take on this role in conversation are paradigms of argumentative virtue. Outside academic circles, however, devil’s advocacy has acquired something of a notorious reputation: real-world conversations are rife with self-proclaimed devil’s advocates who are anything but virtuous. Motivated by this observation, in this paper we offer the first in-depth exploration of non-ideal devil’s advocacy. We draw on recent analyses of two (...) better known discursive practices—mansplaining and trolling—to illuminate some of the signature traits of vicious devil’s advocacy. Building on this comparative examination, we show that all three practices trade on a manipulation of illocutionary force; and we evaluate their respective options for securing plausible deniability. (shrink)