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Jonathan Mayhew Wainwright IV was born at Fort Walla Walla, Washington to Army officer Robert Powell Page Wainwright, a veteran of the Spanish-American War. He graduated from West Point in 1906 and served with the 1st Cavalry Brigade as a commissioned officer until 1908. He saw some combat on a tour in the Philippines before he was sent to France during WW1 in 1918. By the end of WW1 he achieved the permanent rank of Major. During the interwar years, he taught at the Cavalry School at Fort Riley and served at various cavalry units.

In Sep 1940, he was promoted to the temporary rank of Major General and sent to the Philippines under General Douglas MacArthur. When the Japanese invaded the Philippines in Dec 1941, Wainwright was MacArthur's right-hand man in executing the delay action plan to move the troops to Bataan and Corregidor. He became the Allied commander in the Philippines when MacArthur was ordered to go to Australia to assume the position of Allied Supreme Commander. "Goodbye, Jonathan," MacArthur said, in a rare fashion addressing Wainwright by his first name. "When I get back, if you're still on Bataan, I'll make you a lieutenant general." Wainwright responded, heroically and completely ignoring the promise of promotion, "I'll be on Bataan if I'm alive." After a series of valiant efforts to defend the last American holdings in the Philippines, Bataan surrendered on 9 Apr. Lacking food and ammunition, Wainwright and his troops fought on at Corregidor, not surrendering until 6 May. He became a prisoner of war in Japanese camps in Luzon, Formosa, then Manchuria; he was rescued by Russian troops on 20 Aug 1945. During his time in Manchuria, he traded everything from pens to wrist watches for information on MacArthur's advance. When he had heard that MacArthur landed on Leyte, he thought, as he later wrote, "Douglas, true to his promise to me on Corregidor... had come back... come back with a great fleet to support him and manpower beyond the dreams of defeated commanders such as ourselves." His surrender at Corregidor in 1942 haunted him through the entire time he was captured, thinking that he had failed his nation. One of his first questions upon meeting another American was "how am I thought of back in the states?"

Upon release, Wainwright was flown from Mukden to Manila by means of Chungking. He met with Sid Huff, who escorted him to a barber and a tailor. He had lost so much weight that his uniform was loose on his wiry frame. Wainwright then left for Japan, meeting MacArthur on MacArthur's second evening in Japan. MacArthur was not informed of Wainwright's visit, and he was ecstatic when his aide announced his visit. MacArthur recalled:

Wainwright, arm-in-arm with MacArthur, could only respond with "general..." before he broke down in tears. MacArthur did not notice at the time of the reunion, but afterwards he realized that the cane Wainwright walked in on that evening was a present from MacArthur before the war; he had kept it near him through the years in the prison camps. It was given by MacArthur so that his friend, a fellow general, could use it as a swagger stick, a symbol of his rank; ironically, Wainwright used it to support his weakened weight and defeated spirit.

Wainwright was one of MacArthur's guests of honor at the Japanese surrender aboard USS Missouri in Tokyo Bay (British general Arthur Percival was the other, also a prisoner since the start of the war). Wainwright then returned to the Philippines to receive the surrender of the local Japanese commander. He received the Medal of Honor for his valiant though failed attempt to hold the Philippines. The Medal of Honor's citation read:

After the war, he became a four-star general and commanded the US 4th Army at Fort Sam Houston, Texas, United States. He retired from the Army in Aug 1947 and passed away in 1953. He now rests in Arlington National Cemetery, Virginia, United States.

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