This song is about gambling addiction. I don’t think “Dempsey” is in reference to anything (that I could find), but he’s definitely addicted to gambling. It’s “all nerve and no brain” (so, seemingly automatic), he’s already had “a hundred thousand bad throws”, and yet he keeps “dropping it in.” I think the “Someday I” is coming from him. It could either be “someday I will win it all”, or “someday I will stop.” But the sentence is cut off, because neither of those possibilities are true; he’ll never stop and he’ll never win.
This song is about gambling addiction. I don’t think “Dempsey” is in reference to anything (that I could find), but he’s definitely addicted to gambling. It’s “all nerve and no brain” (so, seemingly automatic), he’s already had “a hundred thousand bad throws”, and yet he keeps “dropping it in.” I think the “Someday I” is coming from him. It could either be “someday I will win it all”, or “someday I will stop.” But the sentence is cut off, because neither of those possibilities are true; he’ll never stop and he’ll never win.