It is hard to review African American history without confronting the multiple meanings of debt. There was debt owed, debt paid, debt inherited, and debt hidden in the social tax associated with a subordinate status in the United States. All of these meanings are embedded in the murder of Elmore Bolling. Called Buddy by his relatives, Bolling defied probability by building a highly successful business in Lowndesboro, Alabama, in the 1930s and 1940s. He used debt in a conventional sense, to lease a plantation. Yet his entrepreneurial skills allowed him to offset that debt and amass wealth. He grew corn, cotton, and sugar cane. More impressively, he owned a general store, a gas station, a fleet of trucks, and a catering business, which enabled him to employ at least forty other Black residents. His business acumen allowed him to maintain $40,000 in the bank and another $5,000 in other assets, a remarkable sum for a Black man in the American South during the Jim Crow era.