John D. Rockefeller once controlled 90 percent of the American oil market, yet in old age he handed out dimes on Florida golf courses. This deep dive explores the contradiction at the heart of his life, from a childhood shaped by his con-man father “Devil Bill” and his devout, thrifty mother Eliza, to his love of ledgers as a 16-year-old bookkeeper in Cleveland.

The episode explains how his obsession with eliminating waste, vertical integration, the Cleveland Massacre, secret railroad rebates and drawbacks, and the Standard Oil Trust built a monopoly that also cut kerosene prices dramatically. It then covers Ida Tarbell’s exposé, the 1911 Supreme Court breakup that made him America’s first billionaire, and the methodical philanthropy that reshaped medicine and education.

• How Standard Oil turned gasoline and other refining byproducts into products and cut barrel costs from $2.50 to under a dollar
• Why rivals felt held at gunpoint by a spreadsheet when he absorbed 22 of 26 Cleveland competitors in four months
• How railroad rebates, drawbacks and Samuel Dodd’s trust structure created a national monopoly
• Why breaking Standard Oil into 34 companies during the automobile boom made him richer than ever
• His conditional grants, the University of Chicago, Spelman College and the campaigns against hookworm and yellow fever