This paper is an overview of business strategy and technology in the Gulf of Mexico offshore petroleum industry from its origins in the 1930s through recent developments in deepwater. The story the petroleum industry and the business press tell about offshore oil highlights the ability of entrepreneurial engineering to overcome challenges and liberate extractive enterprise from the limits imposed by the material world. However, we must rigorously examine and contextualize this story, rather than merely celebrate it. Our fascination with technological achievement should not obscure other material factors in the industry's longevity, uneven dynamism, and future. The Gulf of Mexico petroleum province has presented unique challenges and opportunities. Interactions among technology, capital, geology, and the political structure of access in the Gulf of Mexico have generated a functionally and regionally complex extractive industry with a history of resolving the contraction between economies of scale and diseconomies of space, defying critics who have predicted its boom-and-bust demise. Nevertheless, as the Gulf matures, the limits on its potential become more apparent, even with the recent revival of activity in deepwater.