Kermit Roosevelt - Service in World War II

Service in World War II

By 14 October 1939, when Britain was at war with Germany, Roosevelt had negotiated a commission as a Second Lieutenant in the Middlesex Regiment with the assistance of his friend, Winston Churchill, who was by then First Lord of the Admiralty. His first task was to lead a contingent of British volunteers for the Winter War in Finland. According to a contemporary story published in Picture Post, he had resigned from the British Army to lead the expedition. However, before the expedition could be launched, Finland made peace with Russia. Roosevelt served with distinction in a raid into Norway and was later sent to North Africa, where there was little action at the time. He resumed drinking and was debilitated by an enlarged liver complicated by a resurgence of malaria. At the end of 1940, he returned to England and was discharged from the army on health grounds on 2 May 1941, by which time he had once again reached the rank of captain. Roosevelt appealed this discharge all the way to the British Prime Minister, Winston Churchill, who upheld the medical discharge.

When he returned to the US, he turned to drinking to forget his problems. His wife enlisted the help of his cousin, President Franklin D. Roosevelt, who ordered the FBI to track him down, and he was brought back to his family. To extricate him from his current situation, the President gave him a commission as a major in the United States Army, and had him transferred and posted to Fort Richardson, Alaska, where he worked as an intelligence officer and helped establish a territorial militia of Eskimos and Aleuts.