Disposing of his wives. He could have legitimized one of his bastards, but he was smitten of Anne Boleyn—and probably he was the cause of his wives’ lack of fertility. And look at his children. Mary infertile and dead before 40 and Edward dead much younger. And Elizabeth? Was she even fertile? Henry did not die as miserably as Herod, but he did not die well.
VD + Lead poisoning. Yow!