World War I Medal of Honor Recipient. He was issued the award on December 2, 1919 for his actions as a major with Company K, 308th Infantry, 77th Division, US Army, from 2-7 October 1918 at Charlevaux, Binarville, Argonne Forest, France. After graduating from high school in 1901, he attended Williams College in Williamstown, Massachusetts, graduating in 1905. He then attended Harvard Law School and earned his law degree in 1908. He opened a law practice in New York City, New York, and following the US entry into World War I, he joined the US Army, attaining the rank of captain, before he was sent to the Western Front in France. In September 1918 he was placed in command of a battalion and ordered to advance on heavily fortified enemy lines. He and his men were pinned down by German forces and without supplies or food, they managed to hold together against overwhelming odds and refused to surrender. His alleged reply to the German's demand was "Go to Hell." On October 7, 1918, his unit was finally rescued. At the end of the ordeal, out of 550 men only 194 were able to walk out on their own. In recognition of his valor he was promoted to the rank of lieutenant colonel and, along with his Captains George C. McMurtry and Nelson M. Holderman, awarded the Medal of Honor. After the war he returned to law practice but found himself under constant pressure for public appearances. On November 24,, 1921 he booked passage on the S.S. Taloa, a steamer bound for Havana. Two days later, he stayed up late drinking, then went to the rail and jumped overboard in what as presumed to be a suicide and his body was never recovered. He left no explanation, but he had written his will, leaving his property to his mother, before embarking on the journey, and also left several letters in his cabin addressed to family and friends. In 2001, the US television channel Arts and Entertainment (A&E) made a movie called "The Lost Battalion", based on accounts of the battle, with his role portrayed by actor Rick Schroder. His Medal of Honor citation reads: "Although cut off for five days from the remainder of his division, Major Whittlesey maintained his position, which he had reached under orders received for an advance, and held his command, consisting originally of 46 officers and men of the 308th Infantry and of Company K of the 307th Infantry, together in the face of superior numbers of the enemy during the five days. Major Whittlesey and his command were thus cut off, and no rations or other supplies reached him, in spite of determined efforts which were made by his division. On the 4th day Major Whittlesey received from the enemy a written proposition to surrender, which he treated with contempt, although he was at the time out of rations and had suffered a loss of about 50 percent in killed and wounded of his command and was surrounded by the enemy."