In 1966, junior Republican congressional representative Donald Rumsfeld first cut his political teeth leading a campaign against the military-industrial complex. Rumsfeld criticized the impropriety of the relationship between President Johnson and Brown and Root, the military contractor and oil-field services company that was a subsidiary of Halliburton. Decades later, Secretary of Defense Rumsfeld worked alongside Vice-President Dick Cheney, former Halliburton CEO, as the company secured unprecedented contracts during the US war in Iraq. Whereas military contracting had once represented for Rumsfeld the unethical government patronage of the Democratic Party, by the end of the century military contracting signified government thrift, a cost-saving turn to the market in a new era of warfare. Interweaving Rumsfeld’s career with Halliburton’s rise, this article charts Rumsfeld’s strange journey from Halliburton critic to Halliburton champion to highlight this continuity in capitalism and in military contracting across the second half of the twentieth century.