Harvey Cushing overcame tremendous obstacles to his personal and professional development from 1912 to 1919. These trials could have jeopardized the early and necessary formation of the Society of Neurological Surgeons in 1920. War separated young neurosurgeons pursuing the advancement of this “special field,” but Cushing’s principled mentoring of these aspiring surgeons in the midst of this demanding time was unwavering. This historical vignette is a collection of stories composed to highlight certain trainees during this period in his career. It also puts the mentoring relationship into a context that is often encountered today. There is much to learn from those who endure trials of any kind, but there is much more to learn from those, like Cushing, who inspire perseverance in others during their trials.