As best I can tell, I learned this simultaneously from Cisco Houston and Ramblin’ Jack Elliott — the voice I hear singing it in my head is Jack’s, but I can also visualize the page in Cisco’s songbook.
I assumed it was an old cowboy song, but when I set out to learn more about it before writing these notes, no one seemed to be able to trace it further back than Cisco. The tune is old, most commonly used for a song called “State of Arkansas,” about how horrible life was for a settler in that territory, and the theme of “Diamond Joe” is similar enough to suggest that one was composed in emulation of the other — but I couldn’t find anything more about it, except that there are at least two other unrelated songs about a character named Diamond Joe.
However, when I posted the link to this page on Facebook, Andy Hedges alerted me to a post on Robert Waltz and David Engle’s Ballad Index site that tells the whole story: the song was written by Baldwin “Butch” Hawes of the Almanac Singers for one of Alan Lomax’s radio plays, to fit a character in the script named Diamond Joe, and he set it to the tune of “State of Arkansas” because Lee Hayes was scripted to sing it and that was one of Lee’s regular numbers. Cisco was a member of the cast, and started singing it regularly, and everyone else then got it from him.
Anyway, it’s a great lyric, which I’ve always thought of as a companion piece to “The Buffalo Skinners” — they are both eloquent antidotes to all the songs about ridin’ and ropin’ and beautiful sunsets on the prairie, instead focusing on how lousy cowboy work was and how common it was (and is) for bosses to cheat itinerant workers. And Ramblin’ Jack does a fine version of it, which inspired mine, more or less.