The Herndon Climb is an important and meaningful ritual in Naval Academy culture. Scaling of the heavily greased, 21-foot tall Herndon Monument as a group at the very end of the year for ""plebes,"" or freshmen, the Climb marks a major turning point in the lives of all Midshipmen, who are relieved of their low status at the moment they complete the task. The book is culled from interviews with over fifty subjects, including participants in Climbs over the past six decades, with personal observations from the 2019 and 2018 events. Co-author James McNeal recalls the joyful pride of participating in the Climb as a plebe in 1983, and his experience helps bring vivid detail to the memories and reflections of his fellow Midshipmen.

The book also includes a discussion of the career of William Lewis Herndon, whose heroic sacrifice at sea inspired the monument, and also traces the history and development of the modern Climb to its roots in the earliest plebe celebrations, which happened concurrently with every Graduation ceremony at the Academy, as early as 1904.