The general theoretical consensus is that economic growth and development are the product of entrepreneurial activities. Baumol, however, famously observed that not all entrepreneurial activities were economically ‘productive’ and that some entrepreneurial activities were unproductive or even destructive. What is generally not known, however, is how, why, or when destructive entrepreneurship thrives. We begin to unpack the destructive entrepreneurship phenomenon within the context of Haiti. Haiti is an intriguing context of study because, despite extensive efforts to create and develop new institutions to promote productive entrepreneurship, these efforts have been consistently undermined by destructive entrepreneurs. We find in our case study that destructive entrepreneurs strategically protect their entrepreneurial endeavors through various nefarious mechanisms, thereby ensuring the sustainability of their profitable, destructive ventures. The institutional change necessary to economic development is undermined when destructive entrepreneurs have access to and power over the institutional entrepreneurs.