Oliver Market Intelligence

Oliver Market Intelligence

The Original "Sell America" Trade

How Jesse Livermore Made Billions Shorting a Market on the Brink.

Matt Oliver's avatar
Matt Oliver
Feb 18, 2026
∙ Paid

Today, it’s hard to ignore headlines about the “Sell America” trade, betting against U.S. markets as extreme fear grips Wall Street. But nearly a century ago, Jesse Livermore executed the archetype of this trade, shorting stocks during the 1929 crash and walking away with what would today be over $1.5 billion. His story shows how discipline, instinct, a…

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