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Sailing Upwind is more than just another memoir of a distinguished former naval officer's highly diverse career. This book by Admiral James "Sandy" Winnefeld is also intended to offer useful reflections regarding how he accepted and managed risk along the way, as well as a concise description of the qualities one must develop to become a successful leader. Winnefeld began his career as an F-14 fighter pilot and TOPGUN instructor, commanded an aircraft carrier, and then served in a variety of flag officer billets on the way to becoming the Vice Chairman of the Joint Chiefs of Staff.

The ability of the US Navy to fight and win a protracted war in the Pacific was not solely the result of technology, tactics, or leadership. Naval aviation maintenance played a major role in the US victory over Japan in WWII. The naval war against Japan did not achieve sustained success until enough aircraft technicians were available to support the high tempo of aviation operations that fast carrier task force doctrine demanded.

Six weeks after the United States entered World War II, Imperial Japan is annihilating American forces across the Far East while the Nazis stand triumphant over much of Europe. Adolf Hitler's forces are about to commence an assault along the East Coast of the United States, but this "Atlantic Pearl Harbor" would prove far more devastating than Japan's attack on Hawaii. The Western Hemisphere holds the key to victory, but only if the vast economic and military resources of North and South America can be carried across the Atlantic by Allied merchant ships.