This essay is an interdisciplinary study of the ties between human conceptions of wolves and wilderness throughout history. This history between humans and wolves provides a great lens through which to observe the evolution of environmental ethics in the North America. Throughout history, wilderness has represented to the Western World a place of disorder, danger, and evil. In the human eye, wolves came to embody the same deplorable qualities attributed to wilderness. In the first few centuries after European contact, the American wolf population was almost entirely decimated, and the cruelty surrounding the eradication far exceeded measured used on other species, thus indicating a deeply-held contempt for wolves. However, as the 20th century progressed and ecological understanding improved, public notions of both wilderness and wolves began to change. A political battle has ensued over the past few decades to restore wolves to the wilderness they once inhabited, but much of the population still thoroughly opposes the idea. This essay investigates the history behind these shifting paradigms and examines the complications of re-naturalizing a denaturalized modern world.