Best Wishes From Pretty Boy Floyd’s Son
52 Ancestors in 52 Weeks - A Document With Personality
Sometimes the most interesting things in a box of old family photographs aren’t necessarily our family at all.
This photograph is a great example.
The little boy pictured here is Charles Dempsey Floyd, the son of one of Oklahoma’s most infamous outlaws, Charles Arthur “Pretty Boy” Floyd.
Written across the bottom of the photograph in Charles’s own handwriting are the words:
Portrait of Charles Dempsey Floyd son of Pretty Boy Floyd
“Best wishes to Hattie and Jack Mertz.”
Hattie and Jack were my husband’s grandparents, and according to the story passed down in the family, Hattie used to babysit Charles.
Yes, Pretty Boy Floyd’s son.
Hattie and Jack spent their lives in Ponca City, Oklahoma. Charles was born around 1924, the only son of Pretty Boy Floyd and his wife, Ruby. By the early 1930s, Charles’s father had become one of the country’s most notorious fugitives, with his crimes and escapes regularly making newspaper headlines.
The Mertz children including my father-in-law Don (far right) with Charles Dempsey seated in the go-cart. The 3 legged German Shepherd was named Tanya
Exactly how Hattie came to babysit Charles is one of those details I wish someone had thought to ask about while there were still people around who knew the answer.
I don’t know what Hattie thought about babysitting the son of an infamous man. Did she know Charles’s father? Did Ruby bring Charles to her home? Was babysitting him an ordinary occurrence, or did it happen only a few times?
Those are the questions I would love to have been able to ask Hattie.
What I do know is that this wasn’t simply a photograph of a famous outlaw’s son that someone in the family happened to collect. Charles addressed it personally to Hattie and Jack. That little handwritten inscription gives the photograph its personality—and turns an interesting old picture into a piece of our family’s story.
Genealogy has a way of doing that.
Sometimes history isn’t something that happened somewhere else to people we’ve only read about.
Sometimes Grandma babysat it.