The Bad Man of Molino – Railroad Bill No. 2: The Reign of Terror by Sam Castlebury

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By Mike Simmons

Sam Castlebury had created a name for himself. In 1894 and 1895, a desperado named Morris Slater and nicknamed “Railroad Bill” by the media became infamous for terrorizing communities in West Florida and South Alabama. However, the reign of terror of Railroad Bill came to an end when the search for him became so hot that he fled the United States and settled in Africa for a time. When he returned and went back to his old ways of robbery and murder, he was killed in Atmore, Alabama in 1896 and buried in St. John’s Cemetery in Pensacola. But that is another story.

Sam Castlebury lived in the community of Molino, Florida, about 25 miles north of Pensacola. He was born in Alabama in 1872. From an early age, he learned to break into houses and businesses and steal. When he was 17 years old, he was sentenced to serve two years in prison for burglary and theft. As soon as he was released, he went right back to work and was promptly caught again. This time he was given five years.

A man using a turpentine cutter

He was released in 1898. Maybe he learned a lesson. Maybe he learned the wrong lesson. He got a job working at John’s Turpentine Headquarters, eight miles north of Canoe, Alabama. While at work on June 19, became involved in an argument with co-worker Jim Montgomery that turned into a fight. While Montgomery brought his fists, Castlebury brought a turpentine cutter. The cutter won and Castlebury fled, adding murder to his list of misdeeds.

Escambia County, Alabama Sheriff Ed McMillan

Sheriff James McMillan of Escambia County, Alabama swore out a warrant for the arrest of Castlebury, who had fled over into Molino, Florida, his hometown. He armed himself with a firearm, began terrorizing the neighbors, and continued to commit burglaries and other offenses. On June 24, Escambia County, Florida Sheriff George Smith received Sheriff McMillan’s warrant. Smith began his search, he and his deputies hot on Castlebury’s trail. He investigated cases of several burglaries from Molino to Bluff Springs to Millview, obtaining warrants for Castlebury’s arrest. He sent Deputies Sanders and Bobe to Molino. The deputies set out to capture him, but his associates kept a vigilant eye out and informed him each time the deputies came looking. Then, with a stolen gun, Castlebury shot at a man named Richardson near Molino, which sent deputies again searching for him – unsuccessfully.

Escambia County, Florida Sheriff George Smith

Sheriff Smith got reports of crimes committed by Castlebury in Cantonment, Pensacola, and Millview, but no one could find him. He always returned to his stomping grounds – Molino. He was sly, making sure he never stayed in any one place for long and never slept inside. He always slept in the woods.

But that made things worse for those living in Molino – especially the ones living near him. He threatened to kill them if they told the authorities of his whereabouts. As a result, every time a deputy came around hunting for Sam, the neighbors informed him, and he got away. As such, he got quite a reputation – probably inflated more than he earned.  

The media, of course, loved it, and he soon was tagged with the nickname, “Railroad Bill No. 2,” a tip of the hat to Slater. But while Castlebury was terrorizing and Smith was hunting him, the entire north end of Escambia County, Florida lived in fear. Sheriff Smith was swearing in citizen deputies as fast as he could, soliciting help.

Finally, Sheriff Smith had had enough. In early October 1898, he organized a posse, In addition to Deputies Sanders and O’Neal, six armed citizens were deputized to go after “Railroad Bill No. 2.”  

On October 9, Castlebury was walking along a dirt road in Molino, when one of the enemies he had made was hiding behind a tree stump, waiting for him. As he came closer, the man began shooting at Castlebury, striking him twice in the leg. Needing help, he sent his three brothers-in-law after food and ammunition. What he didn’t count on was that the three brothers – Charles, Joe, and Robert Harris – weren’t criminals. They were loyal to their family, but not that loyal. Two members of the posse, Ceasar Marshal and Levi Bailey, located the brothers carrying supplies to Castlebury and stopped them. After searching their belongings and determining that they were probably taking provisions to Castlebury, the three were arrested. It wasn’t much of an interview. They admitted to taking provision to Castlebury, and they agreed to take the deputies to him.

Wilder Creek, Molino, Florida

As they approached his hiding place near Wilder Creek in Molino, the bad man saw them coming. Being injured, he couldn’t run, so he hid himself in the swamp as best he could. The posse spread out and began the search. The search took hours. Finally, as Deputy Oneal was examining the edge of Wilder Creek for any signs, he heard a cough. Deputy Oneal didn’t hesitate to wonder who was coughing; he called for the others and reported that he had found the fugitive. Minutes later, they found him in the creek with only his head sticking out. Suddenly eight guns were pointing at him. He called to them not to shoot. He told them he was wounded, had no cartridges, and was giving up. They placed him under arrest and promptly put him on the first available southbound L&N train with Deputies Sanders and Oneal.

Railroad Tracks, Molino, Florida

That night – Monday night, October 10, 1898 – the L&N train pulled into the station at Alcaniz and Wright Streets in downtown Pensacola to an excited crowd who came to see the Bad Man of Molino. The engineer had wired ahead and let the station know, and word got around. Like a prize Gulf Blue Marlin, Deputies Sanders and Oneal stood proudly beside Castlebury, much to the approval of their fans.

After he pleaded guilty to Assault with intent to commit murder, Sam Castlebury was sentenced to twenty years in state prison. He received an additional twenty for Breaking and Entering – to be served consecutively. By the time the 26-year-old man got out of prison, he had missed the turn of the century, the sinking of the Titanic, World War I, Prohibition, The Great Depression, and the rise of Adolf Hitler. He was released in 1938. He was 66.


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