The legend of John Henry is based on a real person, but the details of his life have been embellished over time. John Henry was likely a steel driver who worked on the railroads in the late 19th century, known for his strength and skill. While the specifics of his feats may be exaggerated, there is historical evidence to suggest that a man named John Henry did exist.
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Probably not. There are no contemporary accounts of the race between man and machine that made John Henry famous. There were many black men driving steel for the railroads in the 1870s, and that name was common. One researcher found a person who claimed to have witnessed the contest at Leeds, Alabama, but that interview occurred 50 years after the song had been written. Another has found there was a Big Bend Tunnel (featured in the earliest versions of the song), a steam drill, and a man named John Henry, during the construction at Talcott, West Virginia. Another believes it could not have taken place at Big Bend, but it may have been at nearby Lewis Tunnel.
A lot of legends but no concrete evidence. If John Henry was a real person, definitive documentation doesn't exist or hasn't been found. Please see the link below for the complete story.
John Henry Nicholson died in 1923.
Henry John Boddington died in 1865.
John Henry Rogers died in 1911.
John Henry Weber died in 1859.