Ride, ride, ride—The true story of America’s most infamous black outlaw

Railroad Bill’s legacy is shrouded in mystery and myth, but today we are publishing a book that reveals the truth behind legend: The Life and Crimes of Railroad Bill: Legendary African American Desperado.

Life_and_Crimes_of_Railroad_Bill“Fascinating. Massey brings to life the stories and mysteries surrounding this legendary figure of the nineteenth-century Southeast and shows how the outlaw has influenced our cultural heritage.”—Susan Reynolds, associate editor, Alabama Heritage

“A compelling and highly readable account of the life of a notorious figure in Florida and Alabama history and how he became the subject of legends and a folk ballad that is still sung today.”—John Burrison, editor of Storytellers: Folktales and Legends from the South

“Gives us a glimpse of how the early railroads—the heart of everyday life at the turn of twentieth century—set the stage for the dramatic exploits of desperate criminals such as Railroad Bill.”—Thomas E. McMillan Jr., Escambia County Historical Society

For more than a year and a half, Railroad Bill eluded sheriffs, private detectives hired by the L&N line, and bounty hunters who traveled across the country to match guns with the legendary desperado. He terrorized busy train lines from east of Mobile to the Florida Panhandle, but as soon as the lawmen got close, he disappeared into the bayous and pine forests—until one day his luck ran out, and he was gunned down inside a general store in Atmore, Alabama.

Little is known about Railroad Bill before his infamy—not his real name or his origins.  Today, Railroad Bill is the subject of many folk songs popularized by singers such as Paul McCartney, Taj Mahal, Gillian Welch, and Ramblin’ Jack Elliot.

But who was he? Where did he come from? What events led to his murderous spree? And why did some view him as a hero? In Railroad Bill, Larry Massey separates fact from myth and teases out elusive truths from tall tales to ultimately reveal the man behind the bandit’s mask.

We talked with Larry L. Massey about the book, his interest in the Railroad Bill, and even his favorite Railroad Bill song. Read our Q&A below:

Larry L. Massey

“Unique should have been Railroad Bill’s nickname. Nearly every incident in his criminal career was unique—each was as profound to law enforcement and the public in the 1890s as they should be to readers today.”—Larry L. Massey

How did you first become interested in Railroad Bill?

I began researching my great, great grandfather, whose history is intertwined with that of Railroad Bill, and the more I unraveled the stories of the two men, the more interested I became in the history of the outlaw.


What makes Railroad Bill such a unique outlaw?

Unique should have been Railroad Bill’s nickname. Nearly every incident in his criminal career was unique—each was as profound to law enforcement and the public in the 1890s as they should be to readers today.  Moreover, he was initially a hardworking turpentine worker who was inoffensive and well liked until a failed attempt to arrest him for carrying a repeating rifle that resulted in a gunfight. He then turned into an outlaw as bold and cunning as one could imagine. He repeatedly demonstrated skill in outmaneuvering the best efforts of railroad detectives, Pinkerton detectives, sheriff’s posses, and private bounty hunters.

What are some of the more common misperceptions about Railroad Bill?  

I believe many performers and admirers of the popular folk song “Railroad Bill” probably believe it is based on a mythical person. But Railroad Bill was real, and he demonstrated a criminal persona equal with stories told of popular western outlaws of the nineteenth century.

There must be so many rumors and stories to choose from. How did you decide which to include in the book?

I sought actual facts for the book, taken from newspaper articles from the 1890s and reports by individuals involved in Railroad Bill’s story. My objective was to tell the entire story as revealed in those sources. The original materials, however, varied considerably. Thus, I addressed that by collecting everything available for a particular event and arranging the information as a mosaic with overlapping pieces of information. With that in view, I was able to see each event more clearly and select the apparent facts that I used to write the book.

 What is your favorite tale about Railroad Bill?

My favorite story about Railroad Bill is true. It is his gunfight with trainmen at Hurricane Bayou in which he singlehandedly fought nearly a dozen armed men.  Alternatively, the inability of authorities to capture the outlaw produced a wave of tongue-in-cheek stories in Escambia County, Alabama, in the 1890s. Those had a single theme: the outlaw could purportedly conjure into an animal or inanimate object to confound his pursuers. I like those stories equally well.

Was there a specific story about Railroad Bill that sparked your interest but that wasn’t included in the book?

Yes. After the book was proof set, I found an 1895 newspaper article with valuable information. The article states that my great-great-grandfather brought Railroad Bill to Alabama from North Carolina. From family tradition, I suspected that to be the case, but I did not have direct evidence. It was too late to integrate into the book text, but I added a paragraph in the preface that reveals some of the information.

Why do you think the folk song “Railroad Bill” has been so popular throughout the years? Which is your favorite version?

I am no musician, but I would say that the rhythm of the song, the simplistic theme relating to a bad man, and the fact that the song from its beginning was part of the folklore have contributed to its success. Also, numerous versions have been performed successfully by commercial artists since the 1920s, thus helping to keep the song popular for more than a century.  My favorite version is the one sung by Frank Hutchison in 1929. It is similar to the version my mother sang to me when I was young.

How does the story of Railroad Bill compare with stories of more well-known outlaws of the nineteenth century?

The story of Railroad Bill is as intriguing and dramatic as the great American stories of Jesse James, John Wesley Harden, Billy the Kid, Rube Burrow, etc. It should stand the test of time in the annals of American history.

Larry L. Massey is an independent writer and researcher living in Mobile, Alabama, and DeLand, Florida. His great-great-grandfather once worked at a Bluff Springs turpentine camp with Railroad Bill.

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