As a philosophy with human problems at its centre and in a time of rapidly changing social conditions, classical Pragmatism engaged an ethics of social radicalism, an ethics that extended as far as human problems do: to the global. To understand how ideas like global justice are generated within pragmatism, it is important to examine not only the thought, but also the activism of pragmatists and how the experimental method of pragmatism was applied to global problems of its day. The life and work of Jane Addams is particularly rich for this kind of investigation. Addams met human problems at both local and global levels with the working hypothesis of applying and observing what a democratic attitude of radical social justice brings to felt indeterminacies. This article begins by comparing and contrasting a pragmatist approach to global justice as opposed to one better known, that of John Rawls, and moves on to examining the difference that Addams’s experience as a woman and an activist makes to how she practiced the pragmatist method in relation to global problems of the Progressive Era.