The Story of Pretty Boy Floyd: The Family Connection My Grandma Never Expected
My great-grandmother never forgot the October day a car drove through her Missouri town announcing that Pretty Boy Floyd was dead. The real surprise came years later, when she says she learned the famous outlaw was connected to the family she had married into.
It all started with one question from my five-year-old, one kitchen table, and a woman my children called Charlotte the Great.
The Story of Pretty Boy Floyd and Our Family Connection
My children were giddy when the small white car pulled into our driveway.
They waited patiently for the woman they called Charlotte the Great to come inside and take her place at the kitchen table.
Once their great-grandmother was settled, they gathered close.
My five-year-old had been learning about history and inventions, and she had a question she had been waiting to ask.
“Charlotte the Great, what is the most memorable historic event of your life?”
Before Charlotte arrived, we had spent the morning guessing what her answer might be.
The automobile?
Television?
Computers?
There was a heavy pause as Charlotte searched through more than 80 years of memories.
Then she began.
“I’m going to tell you a story about me in the third grade. The image is so clear in my mind, even today…”
We leaned closer.
“We had just moved from Wray, Colorado, to Buckner, Missouri. I was coming into the school from recess, and my hand was on the doorknob of the school’s big white doors.”
“It was a chilly day in October. A black automobile with this big speakerphone attached to the roof was coming down the road. The road hadn’t been oiled recently, and dust seemed to swirl eerily around the automobile as it crept down the road.”
“Over the speakerphone, a man was saying, ‘Pretty Boy Floyd is dead! Pretty Boy Floyd is dead!’”
My five-year-old looked at her.
“Who is Pretty Boy Floyd?”
Charlotte looked back at her as though this might be the most surprising question of the day.
“Who is Pretty Boy Floyd?! He was a famous outlaw!”
Then she gave the answer that made every child at the table pay attention.
“He used a machine gun to rob banks and kill people.”
The Childhood Memory Charlotte Never Forgot
Charlotte continued.
“The air was tense with excitement. There were a lot of people who thought this was good news. There had been a shootout in Ohio, and the FBI had killed their man!”
Then her voice turned villainous, the way only Charlotte’s could.
“He was Public Enemy Number One. The most wanted man in America!”
I was confused.
“This is your most memorable historical moment, Grandma?”
Honestly, I was amazed.
She had lived through enormous events. There had been a world war, the Great Depression, and a presidential assassination.
And yet, when we asked which moment had stayed with her, she remembered an outlaw.
Charlotte answered as though there was nothing unusual about it.
“It is. I was a small girl in third grade, and that image of the car driving up and down the street with that speakerphone blaring out that Pretty Boy Floyd was dead stuck with me.”
And really, isn’t that how memory works?
Sometimes the moments that stay with us are not the ones history books tell us should matter most.
Sometimes it is a dusty road.
A black car.
A hand on a schoolhouse door.
And one sentence you never forget.
“Pretty Boy Floyd is dead!”
Then the Story Took a Turn No One Expected
If Charlotte had stopped there, it still would have been a wonderful story.
But she wasn’t finished.
Years passed.
Charlotte grew up and married my Grandpa Max.
Charlotte and Max moved to California to be with his parents.
One day, as a new bride, Charlotte told her mother-in-law the same story she had just told us around the kitchen table.
She told her about third grade.
The big white school doors.
The dusty road.
The black automobile.
And the voice coming through the loudspeaker.
“Pretty Boy Floyd is dead! Pretty Boy Floyd is dead!”
As Charlotte told the story, she noticed that her mother-in-law, Beulah, had turned all shades of red.
Charlotte asked her why.
According to the story Charlotte told our family, Beulah answered:
“Charles Arthur Floyd, also known as Pretty Boy Floyd, was MY first cousin!”
Well.
None of us saw that coming.
The little third-grade girl who had never forgotten the day a car drove through Buckner, Missouri, announcing that Pretty Boy Floyd was dead later married into a family that, according to the story passed down to us, had a connection to that very same man.
What an unexpected ending.
Why I’m Glad My Daughter Asked the Question
What stays with me most is not really Pretty Boy Floyd.
It is the kitchen table.
It is my children gathered around their great-grandmother.
It is Charlotte searching through decades of memories and choosing one small moment from third grade.
My daughter asked a simple question, and because she did, we heard a story I might never have known to ask for myself.
That is the thing about older family stories.
You cannot always guess which memories people are carrying.
You have to ask.
Ask what they remember from childhood.
Ask what frightened them.
Ask what made the whole town stop and listen.
Ask about the people in the old photographs.
Then let them talk.
Sometimes history is closer than we think.
A Note About Our Family Story
This post preserves the story as Charlotte told it to us.
The connection between Beulah Floyd Haynes and Charles Arthur “Pretty Boy” Floyd comes from our family’s oral history and Charlotte’s memory of what her mother-in-law told her. I am sharing it as the story passed down in our family rather than as genealogical proof of the relationship.
For me, preserving Charlotte’s voice and the memory of that afternoon matters most.
Questions Readers May Have About Pretty Boy Floyd
Who was Pretty Boy Floyd?
Charles Arthur “Pretty Boy” Floyd was a famous Depression-era outlaw and bank robber whose name became widely known during the 1930s.
When did Pretty Boy Floyd die?
Pretty Boy Floyd died in October 1934 after being pursued by law enforcement in Ohio.
What is the family connection to Pretty Boy Floyd?
According to the story Charlotte the Great told our family, her mother-in-law, Beulah Floyd Haynes, said that Charles Arthur “Pretty Boy” Floyd was her first cousin.
Has the family connection been documented?
This post preserves the connection as family oral history. It does not present genealogical records proving the relationship.
Why did Charlotte remember Pretty Boy Floyd’s death so clearly?
She said she could still picture herself as a third grader, standing at the school doors while a car drove through town announcing his death over a loudspeaker.
More About Charlotte the Great
The real treasure in this story has always been Charlotte herself. You can read more about the unforgettable woman my children called Charlotte the Great in Charlotte the Great: Rest in Peace.
Final Thoughts
My five-year-old thought she was asking a history question.
Instead, she opened the door to a story that reached from a third-grade classroom in Missouri to our own kitchen table generations later.
That is why I keep telling it.
Ask the question.
Write down the answer.
Keep the photographs.
One day, the story may become the family treasure.
Next story to read: Spend a little more time with the woman behind this memory in Charlotte the Great: Rest in Peace.