Betrayed By “The Woman In Red”: The Death Of John Dillinger

When Chicago resident Ana Sage suddenly found herself living with the notorious John Dillinger, she made a deal with law enforcement to betray him, only to be double-crossed herself

Tim Reynolds
Tales From the Underworld
8 min readMar 15, 2024

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Depiction of John Dillinger (Image generated via Midjourney)

Perhaps the most notorious of all the Depression Era gangsters, John Dillinger’s name is synonymous with the larger-than-life image of the 1930s bank robber and desperado. Even throughout the different variations of the “Dillinger Gang”, it was clear that John Dillinger was the one running the show.

For many average Americans trying to make it through the grinding poverty and despair of the Great Depression, hearing and reading the exploits and accounts of gangsters and bank robbers crisscrossing the Midwest gave them a temporary escape from their own bleak reality.

Unsurprisingly, the banks were not seen by many as sympathetic victims. In fact, many of the banks that Dillinger and company were sticking up were the same…

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