Joseph,
The example you give isn't exactly what I am saying about the Stetson. Here is what I wrote in the article:

So if the Stetson represented manhood, then Stagolee and Billy’s fight for possession of it COULD HAVE BEEN symbolic of the black man’s fight for manhood.

I don't claim to have absolute, undeniable proof that the symbolism existed. It's my theory. And I think theories are useful tools and worth consideration. And I believe that I've found a good bit of evidence which lends creedence to my theory, and other evidence which at least suggests that there is much more to the story than simply one black man killing another black man.

For me, Stagolee is a fascinating puzzle. If Stagolee was simply a cold-blooded killer, why would James Cone write "The victories of Stagolee and High John the Conqueror embodied [an oppressed people’s] struggle for dignity"?

And why would Sterling Brown place Stagolee in a place of honor alongside Casey Jones and John Henry in one of his greatest poems?

He begins it with:

Lemme be wid Casey Jones,
Lemme be wid Stagolee,
Lemme be wid such like men
When Death takes hol' on me,
When Death takes hol' on me.

And ends it with:

An' all dat Big Boy axes
When time comes fo' to go
Lemme be wid John Henry, steel drivin' man
Lemme be wid ole Jazzbo;
Lemme be wid ole Jazzbo.

I don't think that James Cone and Sterling Brown thought Stagolee was a cold-blooded killer. Their writings are pieces of the puzzle; pieces which fit with my theory.

Another piece of the puzzle in my article which fits with my theory deals with Stagolee's reputation as being one of the baddest of all black badmen. It was a much, much "badder" act for a black man to do battle with a white man than simply another black man. And that's because of the consequences of doing such a thing. Professor Molefi Kete Asante, in his book Erasing Racism, points out that “even the baddest man in town would seldom attack the vilest white man.” So if Billy was imagined to be white, we can see Stagolee's badness on display through his actions in the ballad. Of course, we do see Stagolee's badness on display in those versions of the ballad in which he tangles with the devil, but those versions are in the minority.

Your reference to Railroad Bill/Morris Slater suggests to me that you might see him as possessing a much higher degree of badness than Stagolee. And I could see why you might think that. Railroad Bill engaged in a string of gunfights with the law, i.e. the most potent tool of the white power structure. I believe there is even a story of him escaping from one of those gunfights, and then returning to the battle despite the fact that he had already been wounded. Still, I think that Stagolee could be on fairly equal footing with Railroad Bill if we view Billy DeLyon to be a white man.

Jim Hauser
http://theafricanamericanfolklorist.com/2020/11/29/twoblackfreedomsongs/