On December 1, 2016, after a town hall in the English department at the University of Pennsylvania, held to discuss the election of Donald Trump, students tore down a large portrait of William Shakespeare that had adorned the stairway leading to the department for more than 30 years. In its place, they constructed a make-shift portrait on 50 sheets of copy paper of Audre Lorde, a black, lesbian, feminist, activist poet from New York. Perhaps your initial reaction is something like mine: Shakespeare – artistic, humanistic, compassionate – is a friend of the Left. He quite clearly opposed hypocrisy, hatred, and unfairness, so it doesn’t make sense to oppose Trump’s politics of anger, fear, and power by attacking Shakespeare. He is part of the resistance, not the enemy. One thinks of the scene in Julius Caesar where the riotous Roman mob kills Cenna the Poet thinking he is Cinna the conspirator: students at Penn seem to interpret white skin about as well as Shakespeare’s Romans interpret first names. I had to dig a little deeper to understand the affair with Shakespeare’s portrait at Penn, posing three key questions: (1) Why did students take the portrait down? (2) Why did people get so upset when they did? (3) What does the affair reveal to us about the current state of our nation? The answers to these questions revealed Shakespeare to be an unwitting site of predictable disputes in twenty-first-century US politics between the Right and the Left – a Right which values conservation of traditional Western culture and a Left which aims for progress toward something better – but also of conflicts within the Left itself. Specifically, the incident shows the radical, revolutionary wing of the Democratic Party forcing the moderate, centrist branch to take action on values long-held but poorly politicized, resulting in a unified Leftist vision of Western culture that celebrates both conservation of what’s best about the past and progress toward what’s needed in the future.