As a community organizer in Chicago, I work to define, strengthen, and give political structure to democracy's community borders, or what we might call its local frontiers. It will not surprise readers of Alexis de Tocqueville's Democracy in America that the philosophical origins of my profession of community organizing, dedicated as it is both to freedom and equality, are embedded in his writings and reflections. So when I imagine the young Tocqueville equipped with his red bandana, hunting knife, and six-shooter on America's frontier during his great voyage from 1831 to 1832, I see members of my own profession standing with our own weapons of vigilance and resistance on America's contemporary local frontiers. The pivotal question in both Tocqueville's case and our own, of course, is just what frontiers do we seek to define, preserve, or expand with our weaponry? For whom are we establishing such frontiers? Against whom are we protecting them? Are we working to advance what Tocqueville would call in his book “the triumphal progress of civilization across the wilderness”? Or are we seeking to block or retard it, and if so, for what reasons? Finally, given the location of our conference in the same American Midwest whose virgin forests helped shape Tocqueville's own experience of the American frontier, how might his nuanced view of frontier freedom help us understand Chicago today? For Chicago, I will argue, is a city that has repeatedly sacrificed local political frontiers and robust freedom in the name of “triumphal progress” and servile order.