“Whiskey Head” Bill Ryan – Riding With the James Gang

Bill Ryan, James Gang Member

Bill Ryan, James Gang Member

William “Bill” Ryan, who was also known as Tom Hall, “Whiskey Head,” and “Wild Bill,” was a member of the James Gang between 1879 to 1881.

William Ryan was thought to have been born in about 1851 and was said to have been Irish as people often called him “That damned Irishman” Nothing is known of his life before he joined up with Jesse James in 1879. Afterward, he was known as a fearless gunfighter, a braggart, and a heavy drinker.

On October 8, 1879, he was with the gang when they robbed the Chicago and Alton Railroad near Glendale, Missouri making off with about $10,000. Afterward, gang member Tucker Basham, who Bill Ryan had recruited, was captured by a posse and named his accomplices.

However, this didn’t stop the James Gang. Ryan was said to have been involved in the Mammoth Cave, Kentucky Stagecoach Robbery on September 3, 1880; the Mercer, Kentucky Payroll Robbery on October 15, 1880; and the Muscle Shoals, Alabama Payroll Robbery on March 11, 1881.

Jesse James and Bill Ryan Robbing a Stagecoach

Jesse James and Bill Ryan Robbing a Stagecoach

Two weeks after the Alabama heist, his drinking and mouth got him into trouble on March 25, 1881. As he was making his way north to Kentucky, a thunderstorm was gathering, and he took refuge in a saloon at the tiny crossroads of White’s Creek, Tennessee, a few miles north of Nashville. After a few shots of whiskey, he began to run his mouth about being an “outlaw against state, county, and the United States Government!” When one of the customers questioned his credentials, he pulled out his six-guns and, at gunpoint, demanded an apology.

But, Ryan had no way of knowing that the bartender was a Davidson County Magistrate and ex-constable named W. L. Earthman. The bartender then scuffled with Ryan, disarmed him, and placed him under arrest. Whiskey Head Ryan was then taken to the Nashville jail. At that time, both Frank and Jesse James were living in the Nashville area, and when they heard of his arrest, they left the very next day, worried that Ryan would give them up.

In the meantime, Ryan’s identity was soon revealed, and he was returned to Missouri. He was charged with the Glendale train robbery and was convicted on October 15, 1881, based mainly on the testimony of Tucker Bassham. He was sentenced to 25 years and was sent to the Missouri State Penitentiary in Jefferson City. Later his sentence was commuted to ten years, and he was released on April 15, 1889.

He then went to Independence, Missouri, where he stayed with an uncle named John McCloskey. One night, after a bout of heavy drinking, he borrowed a friend’s horse and rode off along the road to Blue Springs, which ran through some heavy woods. The horse returned home without the rider. Ryan was later found with his head smashed in. It was never determined if his death was an accident or from foul play.

© Kathy Weiser-Alexander/Legends of America, updated November 2021.

Also See:

James Gang of Missouri

Jesse James – Folklore Hero or Cold-Blooded Killer?

Outlaw Gangs

Outlaws on the Frontier