I don't think there was a song "If I were a Poor Man", so let's see how I'll do this one...
I'm going to go with my grandfather. He was a carpenter, worked hard, and made a good living. Raising a family, he was never rich, but not poor either. My grandparents had 5 children to raise. In the end, however, after my grandmother died of Alzheimer's, he succumbed to his vices, and despite having two fully paid-off homes in prime real estate areas, he died a poor man. Somehow, he managed to sell his properties and dump all his money into his vice. "Poor judgement" would be an understatement. He died poor, both financially and spiritually, leaving nothing to his children but a sense of neglect and desolation. There is no happy ending to this story.