The primary purpose of this study is to explore a case of remarkably powerful contemporary rhetoric, namely Robert Parker’s wine writing, which has had an unprecedented impact in the world of prestigious wine for more than two decades. Parker, an American autodidact who gave up his career in law to become a fulltime wine critic, is considered the most influential critic of all time. This background motivates the approach of the current enquiry, which targets the persuasiveness in Parker’s writing. The investigation strives to bring to the fore both explicit and implicit elements of his wine reviews that have the potential to contribute to rhetorical success. The material selected for analysis comprises a corpus of reviews extracted from Parker’s extensive bulk of wine writing. The texts are studied against the backdrop of socio-cultural and institutional frames. Considerable importance is assigned to the fact that the reviews occur within a strictly specialized field of discourse with a highly conventionalized configuration. This hermeneutic enquiry approaches the topic from three analytical perspectives, designed to highlight persuasiveness in representations, argumentation and appraisal. The presentation reports on schematic patterns in Parker’s discourse as well as close interpretation of individual texts. The analysis of representations shows that both visual and verbal representations contribute to the persuasiveness of the text. The argumentative exploration of Parker’s discourse, which is assisted by the analytical tools of pragma-dialectics, demonstrates that the reviews involve rational argumentation on several subordinate levels, given in support of assessments and recommendations. Finally, the perspective of appraisal draws on the analytical resources provided by the Appraisal model to shed light on the way in which the audience is positioned to respond with respect to emotional, associative and perceptual values. The results indicate that the persuasiveness of Parker’s discourse arises as a result of concordance among an intricate array of interrelated factors. The audience is recurrently demonstrated to play a crucial role as co-constructors of the message. The present study also has methodological outcomes, presenting a novel combination of analytical methods to perform contextually situated discourse analysis. In addition, the material is allowed to challenge the theoretical ideas and notions that are addressed.