250 Years of American Capitalism: Hamilton, the GFC, & the AI Boom | The Real Eisman Playbook Ep 71

Steve Eisman uses the 250th anniversary of American independence to frame a long view of U.S. economic history, centered on Capitalism in America, the book Alan Greenspan wrote with Adrian Wooldridge. Wooldridge traces his own path into journalism and explains how he came to write with Greenspan, while Eisman steers the conversation toward the big inflection points in American capitalism.

The first major debate is Hamilton versus Jefferson. Wooldridge argues Hamilton won in practice because the United States evolved toward cities, industry, finance, and a stronger central state, while Jefferson’s rural, dispersed vision faded. He also says Hamilton’s protectionist instincts helped infant industries grow, making the U.S. an early model of national economic development.

From there, the discussion moves to railroads, robber barons, and repeated pre-Depression crashes. Wooldridge says the railroads shrank the country, created a national economy, and resembled the AI boom in that they required huge upfront capital, built ahead of demand, and produced gains for the country even as many investors lost money. On the Great Depression, he says FDR helped restore confidence and stabilize the system, though Greenspan was more skeptical of the New Deal.

The Great Financial Crisis becomes the sharpest disagreement. Wooldridge relays Greenspan’s emphasis on Fannie Mae, Freddie Mac, and housing-market regulation, while Eisman argues the deeper problem was excessive bank leverage enabled by risk-weighted assets. Both agree the episode showed how finance had become too detached from the real economy, and Wooldridge closes by stressing that America’s enduring edge is combining well-run corporations with entrepreneurial genius.