Catholic education surfaces as a focus and concern in every age of the U.S. Catholic experience. This article examines the struggles in one, small Midwestern diocese surrounding the establishment and advancement of Catholic education. Personal rivalries, relationship with Rome, local politics, finances, responding to broader social challenges, and the leadership of clergy were prominent themes then, as they are now. Numerous historical insights detailed here help to explain the abiding liberal character of Catholicism in the Midwestern United States.