James O. “Jim” McDonald was the first director of enforcement in the U.S. Environmental Protection Agency’s (EPA’s) Midwest regional office. His privately published autobiography, Holes in My Shoes: Tales of Growing Up in the Great Depression, provides a candid account of his impoverished childhood and his memorable experiences as a soldier, student, journalist, amateur athlete, and public health official. Of particular interest to students of environmental law and enforcement, however, is his account of his critical leadership role as the Midwest regional director of enforcement in the formative years of EPA. A strong-willed, pragmatic, and inspiring manager with an extraordinary talent for complex negotiations and a bold willingness to seize the initiative, McDonald made an unparalleled contribution to building a credible EPA enforcement effort. Under his guidance, the regional office he headed took more than 50% of the Agency’s enforcement actions in its first two years. Joel Mintz, one of Jim’s EPA staff attorneys from 1975 to 1978, and later his longtime mentee, correspondent, and friend until his death in 2018, was provided a copy of Holes in My Shoes with permission to edit and republish all or part of that memoir. This Comment is a modestly edited version of Jim’s account of his pioneering work.