This essay is informed by five different but interrelated conversations all focusing on the relationship between the city and the university. Suggesting the clown as metaphor, I explore the particular role of the activist scholar, and in particular the liberation theologian that is based at the public university, in his or her engagement with the city. Considering the shackles of the city of capital and its twin, the neoliberal university, on the one hand, and the city of vulnerability on the other, I then propose three clown-like postures of solidarity, mutuality and prophecy to resist the shackles of culture and to imagine and embody daring alternatives