The rapid emergence of COVID-19 creates new challenges for the nation’s patchwork of state run workplace benefit delivery systems. This paper draws a comparison between COVID claims and asbestos claims, the “Largest and Longest” wave of occupational disease claims in the United States. The comparison offers insight into avoiding past economic, administrative and benefit delivery pitfalls. The lessons from asbestos claims provide an insight into maintaining a sustainable workers’ compensation system to meet the surge of COVID claims.