Certain figures in history have proved to be particularly polarizing: are they a hero or are they a villain? The answer is rarely one or the other; most are complex individuals that can fit either profile depending on the situation. In the recent past, Chelsea Manning has been such a figure. After leaking thousands of classified and sensitive military and diplomatic documents, she was sentenced to thirty-five years in prison, but her sentence was commuted by President Obama shortly before he left office. Careful examination of Manning’s actions and the culture and events surrounding them will provide readers with a nuanced view of this public figure.