Critical Information Systems (IS) research is sometimes appreciated for the shades of gray it adds to sunny portraits of technology's emancipatory potential. In this article, we revisit a theory about Wikipedia’s putative freedom from the authority of corporate media's editors and authors. We present the curious example of Tim Cook's Wikipedia biography and its history of crowd-sourced editorial decisions, published on Wikipedia's talk pages. We use a hermeneutic method to subject the theory about Wikipedia's “rational discourse” and “emancipatory potential” to a soft, empirical test. When we examined Cook's Wikipedia biography and its editorial decisions, what we found pertained to authoritative discourse – the opposite of “rational discourse” – as well as Jürgen Habermas's concept of dramaturgical action. Our discussion aims to change how critical scholars think about IS's Habermasian theories and emancipatory technology. Our contribution – a critical intervention – is a clear alternative to mainstream IS research's moral prescriptions and mechanistic causes.