The work of 20th Century priest, historian, and social philosopher, Ivan Illich, provides a rich and provocative interpretation of the institutions that contribute to the form of today's cities. Through a broad engagement with Illich's work, his argument that modern institutions had reached a threshold where they were becoming counterproductive will be explored against the backdrop of The Wire. For Illich, the contemporary form of our educational, transportation, religious, and medical institutions were overpowering and degrading our social relations. Thus, today's city was less a sign of hope and more one of tragedy. As such, Illich's fiercely independent and piercing intellect provides unique opportunities to reflect on the city's role in shaping our social existence. Beyond tragedy, Illich articulates a vision of hope rooted in faith.