This article concerns itself with financial traders in Spain who have been diagnosed with gambling disorder. It analyzes what I call the clinical economy of speculation, in which the category of problem gambler is repurposed to draw new lines around proper financial trading. In exploring the expansion of post–financial crisis regulatory mechanisms for credit and debt, as well as widening inequalities across the field of investment, I depict how both traders and clinicians become invested in medicalizing trading as gambling disorder. My theorizing interrogates whether and why common speculative practices are seen as sick and unsafe when everyday people, instead of banks and other financial institutions, perform them. I argue that the pathologized trader is an attempt to regulate, at the individual level, the increasing use of borrowed capital to make financial profits. The commodification of debt, however, is not a gender‐neutral development. Female traders pay a greater price for venturing into the heights of finance. This focus on gender brings into view the redefinition of credit and debt within the domain of trading, and shows the role of debt‐fueled financial speculation in the expansion of financial markets. These ethnographic findings are particularly relevant in a country like Spain, where the Great Recession has bred more new millionaires than ever before, even as the smaller fish of the economy are being medicalized and sometimes even incarcerated.