Military Book Reviews

Sailing Upwind: Leadership and Risk from TopGun to the Situation Room

Sailing Upwind: Leadership and Risk from TopGun to the Situation Room, Admiral Sandy Winnefeld (Naval Institute Press, 2023, 352 p)

The essence of a military officer’s career leadership is difficult to capture in a biography. The book Sailing Upwind is a notable exception! Former Vice Chairman of the Joint Chiefs of Staff (VCJSCS—second highest-ranking US military officer) Admiral Sandy Winnefeld set out to write this book because he “wanted to pass along what [he] learned about problem solving, risk management, and, above all, leadership through the lens of the diverse and exciting career through which [he] was privileged to sail.” The title of the work reflects his approach to pushing as close as possible to the edge of risk while maintaining control. It is like a sailor tacks into the wind without spilling the energy generated by the sails. Winnefeld has thirty-seven years in uniform, which includes nine extended overseas deployments. His service spanned both the Cold War and operations in the Middle East. As the son of a retired navy rear admiral, Winnefeld levied high expectations for himself to become somebody. And somebody of military excellence and prominence he became! 

Winnefeld chose an NROTC scholarship to Georgia Tech instead of attending the Naval Academy like his father. He graduated and was commissioned as an ensign with the class of 1978 and majored in aerospace engineering. He pursued a path in aviation because he always wanted to be a naval aviator. As his path unfolds and his career advances, readers become witnesses to history. Early in his student flying career, we witness the Iran hostage crisis through his eyes as he is learning to fly F-14 Tomcats. Pilots will be fond of these stories in particular. For example, one of the radar intercept officers (RIO) Winnefeld flew with was also the RIO for Vietnam Ace Randy Cunnigham, and the parallels to excellence jump off from there. Winnefeld had the good fortune, as one looks back in time, to be a TopGun instructor in Miramar, CA when the movie of the same name came out. The stories here are surreal for those who lived through this era. I was completing my freshman year in college in Air Force ROTC when this movie came out and it was an inspiration to become a pilot for all aspiring military aviators.

Winnefeld’s writing style is very readable. Without taking himself too seriously, his humanity and humility entice readers to keep turning the pages. He pokes fun at institutions and himself. He covers the difficulties of military life, such as relocating and long periods away from home. Besides just telling us about his exceptional career, a strength of his biography is he shares his leadership lessons and insights. Winnefeld intersperses what he calls Anchors, throughout the book. He delivers these anchors at key junctures of his career. They include Lead Yourself, Lead People, Lead Organizations, Lead Execution, and Lead Change. A short two-to-three-page summation of his thoughts on each of these Anchors, anchor each section. The collection of these pithy and useful sections parallel the levels of responsibility Winnefeld accrues during his career and rise through the ranks. Some lessons he learned are from others, such as Colin Powell, whom he served as an aide-de-camp, and some he came by and adopted as his own because they suited his style.

Ultimately, this biography will stand tall amongst others written during the same era. Personally, I found it readable, realistic, and applicable to my professional and personal life. I believe other readers will too.

Brigadier General (Retired) Chad Manske, USAF was the former Commandant of National War College. He is a prolific reader, author, and publisher of dozens of books and articles. More info:

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