I certainly hope this is fictional.

The song has a terrific melody, and Winchester's vocal is outstanding. At the same time, alas, the character who's telling the story is an appallingly self-centered jerk. From what I've heard, Winchester in the flesh was a low-keyed, likable man, and no legends of narcissism surround him.

If the "Yankee Lady" guy is indeed Winchester, it must have been a very young iteration who knew no better. He certainly didn't know enough not to tell this story as he does here. I would be surprised -- well, actually shocked -- if this song survived in his later repertoire.