Much academic commentary these days concludes that trademark enforcement has become overly aggressive. Commentators argue that the increasingly expansive claims of rights by well-funded trademark owners are unreasonable, and thus that lawsuits asserting those rights amount to trademark bullying. But I think many, if not most, trademark practitioners would take the contrary view that enforcement can only barely keep up with the constantly evolving and worsening threats to their clients' brands, particularly internationally and online. The purpose of this Essay is to try and bridge these two positions by critiquing each one from the perspective of the other. The first step in this exercise is to challenge my own camp, the academic camp, in this debate over the appropriate scope of enforcement. If we academics think that trademark owners are over-enforcing their marks, we should ask ourselves: why would they do that? Why would any trademark owner seek to enforce its marks unreasonably? Why would its trademark attorneys advise it to do so? I will examine these questions in three stages. The first stage is a bare psychological inquiry: what might motivate somebody to do something unreasonable? This is where I will introduce the dichotomy suggested by the title of this Essay (with 3 apologies to the late Hunter S. Thompson). The second stage is a doctrinal inquiry: once we think we understand trademark owners' psychological motivations, we can look at the law's role in mediating them. In particular, we ought to ask whether trademark doctrine is generating these motivations or responding to them in some way. The third stage of the inquiry looks to the profession as the nexus of doctrine and action and questions the role of trademark attorneys in mediating these dynamics and advising their clients.