Episode 251: Glenn Stout Brings to Life The Tiger Girl and the Candy Kid: America’s First Gangster Couple

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By Brendan O’Meara

Glenn Stout returns for his fifth time to the podcast, this time to talk about his thrilling new book The Tiger Girl and the Candy Kid: America’s First Gangster Couple.

The book takes us to the 1920s, a time when wars were supposed to be a thing of the past, a pandemic wiped across the globe, and veterans coming from the Great War had little support at home. I’m glad all those things are a relic of the 20th century.

Richard Reese Whittemore and his wife Margaret were working class kids who decided it best to live the life they saw on Instagram, or the equivalent of it at the time. Richard was in and out of jail and when he violently broke out of prison, he teamed up with criminal masterminds to steal valuable jewels in coordinated attacks in well tailored suits that took all of 20 seconds. They made a lot of money and spent just as much. Richard and Margaret played up their marriage for the press and what we saw here was a man willing to die for love and Margaret would be there by his side until the bitter end. 

Here’s some jacket copy:


Set against the backdrop of the excesses of the RoaringTwenties, their story takes us from the jailhouse to the speakeasy, from the cabarets where they celebrated good times to the gallows where their story finally came to an end… and left Tiger Girl pining for a final kiss. Tiger Girl and the Candy Kid is a tale of rags to riches, tragedy and infamy.

We talk a lot about how he built the scenes and layered the work to create this three-dimensional landscape of a time and a place that’s foreign to us yet entirely relatable.

We dig into how he went about the research, what the Roaring Twenties of the 20th century says about the 20s of our current moment, fame then and now, and much more.

If you dig this, it pairs well with each of his previous four trips, but also with Bob Batchelor, Stephanie Gorton, Catherine Grace Katz, and Paul Willetts, just to name a few past CNFin’ guests.

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