The chapter analyzes Bertrand Russell’s critical engagement with Dewey’s philosophy (primarily Logic: The Theory of Inquiry) in his “Dewey’s New Logic” from 1939. The opening part of the chapter provides a brief description of the decades-long interaction between Russell and Dewey. It then goes on to not only describe the views regarding ‘holism,’ ‘instrumentalism,’ and ‘knowledge and success’ that Russell attributes to Dewey but also explain how Russell thinks that even the strongest versions of these views are deeply problematic. The second part of the chapter continues by assessing the views that Russell attributes to Dewey as well as Russell’s assessment of these views. Here, the main conclusions are that Russell not only often misunderstands Dewey’s actual views but in several cases judges them by means of criteria that Dewey would reject. His attribution of a kind of holism to Dewey, so it is argued, is, for example, based on a misunderstanding of Dewey’s idea of a situation, just as it makes Russell overlook the fact that situations in Dewey’s philosophy actually function as the kind of logically separable individuals that Russell takes to be presupposed by empirical knowledge. In a similar way, Russell also presupposes sharp distinctions between theory and practice, science and common sense, as well as logic and politics that Dewey would reject. Despite Russell’s failed attempt to engage with Dewey’s philosophy from the inside, however, the chapter ends by suggesting that they actually share a common concern for the future of intellectual joy in the age of industrialism and collective enterprise—something which might serve as a point of reference for future dialogue.