Robomatic,
I agree with what you're saying about machines and technological innovation. I wouldn't refer to John Henry as a Luddite though because I don't believe that the race with the drill had anything to do with saving the jobs of manual laborers. The idea that the race was some kind of test to determine whether steam drills should replace workers is, of course, ridiculous. As you have pointed out, workers have to sleep and rest; machines don't. Also, for the investment in a steam drill to pay off, you'd have to replace a large number of workers, not just one. Therefore, a steam drill competing against only one man (John Henry) is not a good test of whether you should replace a group of men with a machine. You could argue that John Henry was the equivalent of a whole group of steel drivers, but that's the stuff of legend, not reality.

If you really want to explore what could possibly have sparked the legend, you need to consider the story of John Henry in its historical context: the oppression and exploitation of black people. (Unfortunately, popularization of the ballad has taken it out of this context.) Black workers picking cotton on the plantations, constructing and repairing levees along the Mississippi, loading and unloading cargo carried on riverboats, and laying track and carving out tunnels for the railroads contributed largely to turning America into an agricultural and industrial powerhouse. But these workers were terribly abused and exploited by their employers/bosses/overseers/captains. Largely, they were victims of peonage on plantations and in levee camps and other work camps. Other workers endured incredibly cruel conditions on prison farms and under the convict lease system. So telling the story of John Henry winning a contest against the steam drill was a way for black people to defeat their oppressors without having to pay the consequences. It was sort of like the black boxer Jack Johnson defeating a white man for the heavyweight championship. In a contest, a black man could defeat a white man--actually beat him up, in the case of Johnson--without any backlash from whites. Keep in mind that, in many versions of the ballad, John Henry refers to the drill as YOUR drill while addressing the captain. His victory over the drill represented a victory over his cruel racist white boss.

I believe that it's quite possible that a man named John Henry did race a drill--not to save jobs, but as a sporting event. But I also believe that there is a very real possibility that it never happened at all. Regarding this second possibility, it could have been a piece of creative storytelling invented by a black tunnel worker to honor a fallen co-worker who was "bad" enough to challenge a cruel captain and then paid for his insubordination with his life. In telling the story of his friend, he could have described John Henry as being "so bad that he could outhammer a steamdrill. Singlehandedly!" With that bit of exaggeration, the legend could have been off and running. (By the way,Zora Neale Hurston's book Mules and Men is a wonderful source for hearing great black storytelling.)

Jim