Mega-events like the Olympic Games remain widely recognized as key opportunities for cities to accelerate large-scale urban development projects through the construction of extensive Olympic Villages complexes. However, in the current global financial climate, these debt-financed urban renewal strategies are fraught with risk for both public and private partners. In the first part of this paper, I explore how the city of Vancouver, British Columbia, inherited the entire responsibility for the construction of the 2010 Winter Olympic Village following the 2008 global economic crisis and a number of undisclosed local political commitments. In what follows, I raise some political questions about the democratic limitations of the entrepreneurial urban policy - making context and the disproportionate transfer of financial risk associated with these developments to the public sector. Finally, I draw parallels between the experiences of Vancouver and the recent government bailout of the Olympic Village development in East London.