Both John Dewey and Jane Addams believed that the cure for the ills of democracy is more democracy. While their vision of democracy is rightly called radical, the processes through which they proposed to cure the ills of democracy are in large measure conservative, in the classical, Burkean sense of the term. To show this, I first explain how well their political philosophies line up, particularly their proposals for political reconstruction. I then use Addams’s experiences as a delegate to the 1912 Progressive Party Convention as a test case in real time for Dewey’s proposals for political reconstruction. The compromises she made there demonstrate the Burkean conservative character of the process of pragmatist change, as well as reveal how the tragic resides within pragmatist efforts at social reconstruction.