We discuss a famous speech by Jane Addams titled, A Modern Lear, her reflections on the events leading to and during the infamous Pullman Railway Strike of 1894. Using ideas drawn from the emergence of classic pragmatism and Shakespeare’s King Lear as an analogy, Addams took both the ownership and workers to task for the violence and provides a way to avoid a recurrence of such a tragedy. What insights are applicable to today’s contemporary situation? Can pragmatism provide a way forward?