Chapter 9, “The 2016 Presidential Election and the First Woman President?”, chronicles the distinctive 2016 campaign of former U.S. Senator and Secretary of State Hillary Clinton to become the first woman president. She was routinely considered the most likely Democrat to seek this office after the 2012 election. She won the Democratic Party nomination after a hard-fought campaign against independent Senator Bernie Sanders and was the frontrunner during most of the general election campaign. Although winning nearly three million more votes than Republican nominee Donald Trump, she ultimately lost the all-important Electoral College vote that gave the election to Trump. This chapter highlights the gendered aspects of both the nomination and the general election phase of the campaign, given the historic nature of Hillary Clinton’s candidacy. Gender became a factor in ways not imagined at the beginning of the campaign season. It could not be otherwise. This chapter tells how she lost and who voted for and against her.