In 2016, Hillary Clinton was the first woman to gain the presidential nomination from a major political party in the United States, yet she was unsuccessful. The current study explores barriers to being elected as president for women generally and Hillary Clinton specifically. Using the propositions and tools of affect control theory, we demonstrate how women’s political representation shapes cultural sentiments about women and the president. In a nationwide sample of Americans surveyed shortly before the election, we find women’s representation on the state level influences voter preferences through these cultural sentiments: More women in politics makes a woman president feel less deflecting, which is associated with a greater likelihood of voting for Clinton. We also demonstrate how sentiments about Clinton—as an individual, not merely a woman running for president—conflict with Democratic voters’ expectations for presidential qualities and behaviors, which may have further prevented victory in 2016.