This paper is a critical case study tracing the professional history of a self-professed open educator over more than two decades. It frames the narrative of an individual as a window on the broader arc of the field, from early open learning as a means of widening participation, through the rise of the participatory web at scale, to the current datafied and extractive infrastructure of higher education. It outlines how the field of online education has changed, as the web and the social and societal forces shaping use of the web have shifted. Through these lenses of change, the case study explores the dilemma facing open and participatory education at this juncture: that the current structure of the web threatens privacy, higher education governance structures, and the spirit of open, participatory sharing. The paper explores the problem of the web as one without direct solutions but does consider ways that educators might mitigate their open practice in more critical directions.