How are brands navigating the tension between being a cultural and a market player in woke times? Brand activism resonates of the struggle that brands undertake to be perceived by consumers as committed cultural authority. This led several brands to fall into woke washing allegations and contestations in social media. Our study dives deep into a successful but highly contested Italian media brand – Freeda Media – that was launched as a cultural resource for the feminist cause but suffered from strong consumers’ critique. Findings reveal how emerging contestation and polarization generated by brand activism in social media are the result of the unresolved tension of the brand between being a cultural and a market player. This tension produces a spiral of mismatches between brand conduct and consumer perceptions when the commercial goals of the brand as a market player prevail over the cultural value of material and immaterial resources provided by the brand as a cultural player.