Sid Stockdale ’73, distinguished alumnus, former faculty member, current board member, and son of the late Vice Admiral James Stockdale, joined South Kent School for a Virtual Pathways conversation. This special event serves as a preview to Sid’s upcoming Veterans Day keynote on November 12th, where he will share the remarkable story of his parents, Admiral James and Sybil Stockdale, Founder of National League of POW Families, the namesakes of South Kent’s hockey arena, the Admiral James and Sybil Stockdale Arena.
Sid will return to campus on November 12th to speak live to students. His talk will reflect on the enduring lessons of leadership, sacrifice, and resilience that his family’s story represents, and the principles that are also central to South Kent’s Stockdale Leadership Academy.
In this virtual session, Sid offered a personal and moving account of his journey to South Kent and his life growing up as the son of one of America’s most respected military leaders. His recently published book serves as the basis for much of the conversation, offering candid reflections on family, identity, and what it means to live in the shadow, and light of greatness.
His father, Vice Admiral James Stockdale, the legendary naval aviator and Medal of Honor recipient, is one of the most decorated officers in U.S. Navy history. Stockdale is also the namesake of the Stockdale Center for Ethical Leadership at the Navy Leadership Academy. Captured during the Vietnam War, Admiral Stockdale spent over seven years as a prisoner of war, during which he withstood extraordinary hardship and became a symbol of Stoic virtues of courage, moral clarity, and unwavering honor.
Beyond his military service, Admiral Stockdale was a noted scholar of philosophy and ethics, and even a vice-presidential candidate in 1992. His principled leadership and intellectual rigor continue to influence generations of leaders and thinkers.
Sid’s talk is more than a historical reflection, it’s a deeply personal story of family values, quiet strength, and the lifelong impact of growing up under the example of a true American hero. His session will include a brief presentation followed by an open Q&A, allowing students to engage directly with this powerful narrative.
This is a rare and meaningful opportunity to connect with the Stockdale legacy firsthand and to reflect on the deeper meaning of service, leadership, and what it truly means to live a life of purpose.
Watch Sid’s Virtual Pathways Talk Here and read Sid’s book: A World Apart, Growing Up Stockdale
