Matthew Cox | Inside True Crime Podcast
America’s Greatest Bank Robber? Inside the Life of Pretty Boy Floyd
31 May 2025
Pretty Boy Floyd was a gangster you did not want to mess with, and during his spree of bank robberies he became somewhat of a folk hero for the locals, robbing the rich and giving to the poor. But Pretty Boy Floyd would face off with the cops one too many times and ultimately catch a bullet, but his story has gone down in history. In today's new video we're going to show you the rise and fall of one of histories most notorious gangsters, Pretty Boy Floyd.Contact Tim [email protected] me on all socials!Instagram: https://www.instagram.com/insidetruecrime/TikTok: https://www.tiktok.com/@matthewcoxtruecrimeDo you want to be a guest? Fill out the form https://forms.gle/5H7FnhvMHKtUnq7k7Send me an email here: [email protected] you want a custom "con man" painting to shown up at your doorstep every month? Subscribe to my Patreon: https: //www.patreon.com/insidetruecrimeDo you want a custom painting done by me? Check out my Etsy Store: https://www.etsy.com/shop/coxpopartListen to my True Crime Podcasts anywhere: https://anchor.fm/mattcox Check out my true crime books! Shark in the Housing Pool: https://www.amazon.com/dp/B0851KBYCFBent: https://www.amazon.com/dp/B0BV4GC7TMIt's Insanity: https://www.amazon.com/dp/B08KFYXKK8Devil Exposed: https://www.amazon.com/dp/B08TH1WT5GDevil Exposed (The Abridgment): https://www.amazon.com/dp/1070682438The Program: https://www.amazon.com/dp/B0858W4G3KBailout: https://www.barnesandnoble.com/w/bailout-matthew-cox/1142275402Dude, Where's My Hand-Grenade?: https://www.amazon.com/dp/B0BXNFHBDF/ref=tmm_pap_swatch_0?_encoding=UTF8&qid=1678623676&sr=1-1Checkout my disturbingly twisted satiric novel!Stranger Danger: https://www.amazon.com/dp/B0BSWQP3WXIf you would like to support me directly, I accept donations here:Paypal: https://www.paypal.me/MattCox69Cashapp: $coxcon69 Learn more about your ad choices. Visit megaphone.fm/adchoices
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He got in there and somehow broke out and flung himself out of a window. I have no idea how he got rid of the handcuffs. He got away. Boyd ended up running up the hill with a machine gun. Took a couple shots at the deputies. That sentence was never served.
Had to jump from a moving train.
You know, he still wanted for escaping from his 12 to 15 year sentence. He was the second person to be named public enemy number one. You know, when he was... in the Wellsville area.
At one point, he then got in a shootout with the Wellsville chief of police and two of his erstwhile deputies, and Floyd ended up running up the hill with the machine gun, took a couple shots at the deputies, and the gun jammed, and he had literally tossed it under a rabbit hutch. because I don't know if you've ever picked up a Thompson, but I think they weigh about 16 pounds.
It would not be something you'd want to carry. if it wasn't useful to you. So he dumped it. And one of the neighborhood children who was still living at the time I got interested explained to me how the neighborhood kids found the gun under the rabbit hutch. And this guy was still mad that they took it off of him. So he thought that he should get to keep that. But the FBI ended up with it.
So... Well, let's start, if you don't mind, we kind of start at the beginning of his life. Where was Floyd born and what was his full name? I know his mom didn't name him Pretty Boy.
No, definitely not. The actual name is Charles Arthur Floyd. And the Floyds were from northwestern Georgia, I believe Bartow County. They were farm people, country people. At one point, I saw some suggestion that there was some distant connection to a Confederate general whose name was Floyd, who was singularly unnoteworthy in what he did for the Confederacy. But there may be a connection there.
But the family had moved to Oklahoma. A lot of times they're compared to the Jodes, you know, Grapes of Wrath kind of thing, although I think the Jodes were moving from Oklahoma to California when they were made famous in Steinbeck's novel. But there are a lot of comparisons. They were not well-to-do people.
Although I did find it interesting in talking to some of the nephews, who unfortunately have all passed now, that Charlie is the only one in the family who ever was convicted of any serious crime. In fact, one of his brothers, after Charlie died, became the sheriff of Sequoia County, Oklahoma. And one of the nephews was an accountant. And I remember him being very interested in the fact.
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