Literary and historical sources assumed ulterior, even diabolical, motives in the man who voluntarily became a eunuch. If he was lucky, he could become the ruler’s confidant and even usurp imperial power. Focusing on Ming eunuch Wei Zhongxian (1568–1627), the article addresses key questions in the portrayal of eunuchs: How and why did a man become a eunuch? What were his motives, as far as can be learned from historical cases; and what did storytellers and other writers think his motives were? In the case of powerful and influential eunuchs, the question also became, how, after his act of self-destruction, did the eunuch reconstruct himself? How did he re-create himself as a newly potent man?