This article examines the historical trajectory of unemployment in the Illawarra region. As part of this analysis, aggregate employment levels are contextualised within the framework of local economic conditions and industry. While the levels of unemployment in the ‘bitter years’ of the Great Depression were high, the region’s unemployment woes were most acutely felt during the early 1980s when unemployment skyrocketed due to severe economic contractions within the region’s largest employer, BHP. More recently the impacts of the global financial crisis have led to stymied economic growth with unemployment remaining higher than state and national averages. At the time of writing, further job losses are occurring within local industry and the usual policy approaches by government to address declining competitiveness and profitability remain at best, temporary. The article concludes by considering the legacy of unemployment in the region and prospects for the future.