This paper explores the history of sovereign debt default in developing economies and attempts to highlight the mistakes and accomplishments toward achieving debt sustainability. In the past century, developing economies have received considerable investment due to higher returns and a degree of disregard for the risks accompanying these investments. As the former Citibank chairman, Walter Wriston articulated, "Countries don't go bust" (This Time is Different, 51). Still, unexpected negative externalities have shattered this idea as the majority of developing economies follow a cyclical pattern of default. As coined by Reinhart and Rogoff, sovereign governments that fall into this continuous cycle have become known as serial defaulters. Most developed markets have not defaulted since World War II, thus escaping this persistent trap. Still, there have been developing economies that have been able to transition out of serial defaulting. These economies are able to leverage debt to compound growth without incurring the protracted consequences of a default. Although the cases are few, we argue that developing markets such as Chile, Mexico, Russia, and Uruguay have been able to escape this vicious cycle. Thus, our research indicates that collaborative debt restructurings coupled with long term economic policies are imperative to transitioning out of debt intolerance and into a sustainable debt position. Successful economies are able to leverage debt to create strong foundational growth rather than gambling with debt in the hopes of achieving rapid catch- up growth.