Pretty Boy Floyd: The Notorious Life and Death of the Depression Era Outlaw

By: Charles River Editors

Narrated by: Scott Clem

"If you'll gather 'round me, children, a story I will tell
'Bout Pretty Boy Floyd, an Outlaw, Oklahoma knew him well." [Woody Guthrie, “The Ballad of Pretty Boy Floyd” (1939)]

November 1, 1932 was a fine autumn day in the sleepy, cotton-farming city of Sallisaw, Oklahoma, the heart of Sequoyah County. The blinding rays of the midday sun were shining their brightest, but the otherwise blistering heat was offset by a brisk breeze. These were ideal conditions for a Tuesday, a seemingly pedestrian day of the week, but what was unfolding in the Sallisaw State Bank was anything but ordinary.

At first glance, it would seem as if a traveling carnival or a homegrown celebrity had come to town. The sidewalks of the city bank and its surrounding establishments were teeming with locals, generations of families, young lovebirds, and clusters of friends. Indeed, they had convened to witness a spectacle, albeit one of an entirely different sort.

The doors of the Sallisaw State Bank swung open with a resounding bang, signaling the start of the show. Out staggered a pair of thieves, each toting bulging sacks of bills and coins and glinting Colt .45s. The hogtied tellers inside the bank desperately wriggled across the floor to voice their distress, craning their necks and directing their muffled screams toward the open door. One had even managed to squirm out of his gag and was calling out to the crowd across the street for help. Unfortunately, his cries were negated, not by the spectators' own cries of alarm but by thunderous applause, supplemented by whoops, whistles, and a constellation of waving handkerchiefs. Some of those who cleared the path for the robbers' getaway car were supposedly patrons present in the establishment during the stick-up itself.

The ringleader, a striking young gentleman with a square jaw, a smoldering squint, and dark hair slicked back with scented pomade, acknowledged his admirers with a quick nod before ducking into the running vehicle. According to local lore, quite a few of the spectators had been briefed on the robbery beforehand by none other than the ringleader himself. So bold was he in his endeavors that he strolled into the bank's neighboring establishments in the days prior and simply asked its proprietors to refrain from ringing the cops, to which they gladly agreed. He even left those complicit with enough time to extract their savings from the bank.

The dashing ringleader, hailed by many as the “Robin Hood of Cookson Hills”, was none other than Pretty Boy Floyd, a perplexing character as abhorred as he was revered. To the feds, Pretty Boy Floyd was a venomous, manipulative scoundrel who was egregiously lionized as an antihero with a heart of gold. A career bank robber supposedly associated with up to 40 bank robberies, his face would soon be plastered on the 1934 poster of the FBI's Most Wanted alongside John Dillinger, Baby Face Nelson, and Alvin Karper.

©2019 Charles River Editors (P)2019 Charles River Editors