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In August 2017, the mayor of São Paulo, João Doria, mediated an arbitration between billionaire TV presenter Silvio Santos and legendary theater director Zé Celso, aiming to settle a decades-long dispute over Santos’s proposal to build luxury high-rises in the property that surrounds Zé Celso’s historic Teatro Oficina. At stake in this meeting, however, was much more than the future of one block in the largest city in the Americas. Each in their own way, the three characters in this peculiar scene are enmeshed with the history and the present of the city of São Paulo. This paper presents a close reading of the epistemological clash that this meeting represents, from the six decades of protagonism of Silvio Santos and Zé Celso to the tensions inherent in Brazil’s own version of the global turn toward the far right. This dispute over Teatro Oficina thus serves as a particularly charged stage to reveal competing visions for the city of São Paulo, both in the past and in the present.