Roosevelt was the only general on D-Day to land by sea with the first wave of troops. At 56, he was the oldest man in the invasion, and the only one whose son also landed that day; Captain Quentin Roosevelt II was among the first wave of soldiers at Omaha Beach.
Brigadier General Roosevelt was one of the first soldiers, along with Captain Leonard T. Schroeder Jr., off his landing craft as he led the 8th Infantry Regiment and 70th Tank Battalion landing at Utah Beach.
Throughout World War II, Roosevelt suffered from health problems. He had arthritis, mostly from old World War I injuries, and walked with a cane. He also had heart trouble, which he kept secret from army doctors and his superiors.
On July 12, 1944, a little over one month after the landing at Utah Beach, Roosevelt died of a heart attack in Méautis, 22 km from Sainte-Mère-Église in Normandy. He was living at the time in a converted sleeping truck, captured a few days before from the Germans. He had spent part of the day in a long conversation with his son, Captain Quentin Roosevelt II, who had also landed at Normandy on D-Day. He was stricken at about 10:00 PM, attended by medical help, and died at about midnight. He was fifty-six years old. On the day of his death, he had been selected by Lieutenant General Omar Bradley, now commanding the U.S. First Army, for promotion to the two-star rank of major general and command of the 90th Infantry Division. These recommendations were sent to General Eisenhower, now the Supreme Allied Commander in Europe, for approval. When Eisenhower called the next morning to approve them, he was told that Roosevelt had died during the night.