Everyone knows that the Roosevelt family held a political dynasty for decades; fielding two presidents of the United States and a first lady in 50 years is a pretty impressive record, and that’s without mentioning all the other jobs like assistant secretary of the Navy (Theodore and Franklin) and Governor of the State of New York (Franklin).
But the Roosevelts actually have a strong claim to a military dynasty as well with three Medals of Honor, a Navy Cross, 11 Silver Stars, and a slew of other awards from the U.S., France, and Britain, all in 100 years.
So, you know, awkward Christmases for the cousin who went into finance.
The Roosevelt military legacy dates back to the Revolutionary War when Henry Rutgers (a descendant of Elsie Roosevelt) and Nicholas Roosevelt served on the American side. But it really got steaming in the Civil War when two of Theodore Roosevelt’s uncles served the Confederate Navy.
While the Roosevelt family was based in New York, Theodore’s father had married Martha Bulloch, a Souther belle whose family had deep ties to what would become the Confederacy. When the war broke out, two of her brothers volunteered for service.
James and Irvine Bulloch became naval officers, and both brothers were involved in launching the CSS Alabama, one of the most feared Confederate commerce raiders in the war. James, by that point assigned to secretly buying ships for the Southern Navy from English shipyards, commissioned the ship and supervised its construction.
But the Union State Department was working feverishly to get the future Confederate ships in England seized, so Irvine led a “sea trial” of the Alabama before stealing away with it to the Azores to receive its crew and weapons. Irvine would serve on the vessel for most of the war as a midshipman and is credited with firing the Alabama’s last shot before it was sunk at Cherbourg, France, in battle against the USS Kearsarge.
All of this had an effect on the brother’s nephew, Theodore Roosevelt, Jr., who, from the age of 5, was noted as having idolized the Bulloch side of the family and their sense of adventure. He loved his father, but is thought to have been deeply embarrassed about his father’s having purchased a substitute for his place in the Civil War.
One of Theodore’s cousins did distinguish himself in the war, though. First Sgt. George Washington Roosevelt received the Medal of Honor for recapturing his unit’s colors and capturing a Confederate color bearer at the Second Battle of Bull Run.
While young Theodore grew up with the New York side of the family and entered politics, those stories from his uncles were still rattling around his head when the U.S. entered the Spanish-American War.
Theodore resigned his position as the Assistant Secretary of the Navy to form the First U.S. Volunteer Cavalry, “Roosevelt’s Rough Riders.” They participated in two major battles. The first was the Battle of Las Quasimas and the Battle of San Juan Heights where, on July 1, 1898, Theodore Jr. led multiple charges for which he would posthumously receive the Medal of Honor in 2001.
When the Lusitania was sunk and America finally entered World War I, Theodore Jr., a former president by that point, was turned down for service. But three of his sons were accepted into the U.S. Army and a fourth, Kermit, volunteered for service in the British army where he was accepted and rose to captain.
Capt. Quentin Roosevelt was the youngest of the four brothers and the only one who died in the conflict. He trained hard as a pilot, rose to squadron commander, and had one confirmed kill before being engaged by three enemy planes and killed during the Second Battle of the Marne. He was awarded the French Croix de Guerre.
Theodore III, and Archibald Roosevelt were commissioned as a, Army major and lieutenant, respectively, and joined the 1st Infantry Division. Kermit accepted a commission as a captain in the British army.
Kermit was sent to the Middle East where he earned a British Military Cross for bravery after capturing Turkish soldiers in the Battle for Baghdad. Archibald received two Silver Stars and a Croix de Guerre, and Theodore received the Distinguished Service Cross, two Silver Stars, the Croix de Guerre, and the Chevalier de la Legion d’Honneur, all awards for high valor. Theodore was gassed once and Archibald was crippled by shrapnel.
After America entered World War II, Theodore III returned to service as a colonel. He rejoined the 1st Infantry Division where he was joined by his youngest son, Capt. Quentin Roosevelt II. They were sent first to North Africa.
It was there that the men earned three Silver Stars. Quentin earned the first at the Battle of Kasserine Pass when he manned an artillery observation post under fire and used it to help hold back German Field Marshall Erwin Rommel’s attack until a Messerschmitt shot him through the back.
Theodore, a brigadier general by that point, then earned two more. His first World War II Silver Star came when he manned an observation post under attack from German dive bombers, fighter planes, and artillery. He earned his next Silver Star, his fourth overall, the next day when he led a reinforced combat team against enemy machine gun positions.
Quentin was sent to recover from his wounds but the men were reunited at D-Day when Quentin hit Omaha Beach and Theodore personally directed the 4th Infantry Divisions landings at Utah Beach, redrawing the division’s attack plans while under fire. He would later receive a Medal of Honor and recommendation for promotion to major general, but he died before he received either.
Quentin II would receive the Croix de Guerre before the war ended.
Archibald, meanwhile, had received full disability after World War I but returned to the Army for World War II and once again received two Silver Stars and was wounded. According to Military Times’ Hall of Valor, that made him the only U.S. service member to receive full disability for two different wars.
Meanwhile, two sons of then-President Franklin D. Roosevelt and distant cousins to Theodore’s family also distinguished themselves in World War II. James R. Roosevelt received a “SPOT AWARD” of the Navy Cross for his leadership under fire with the Marines on Makin Island during a 1942 raid. A year later, he received a Silver Star as a lieutenant colonel for leading assaults to capture the same island.
Navy Lt. Franklin D. Roosevelt, Jr., received the Silver Star in 1943 for rendering aid and rescuing two men wounded by shrapnel during an air raid in Palerno, Sicily.
Finally, in 1955, Air Force Capt. Theodore S. Roosevelt, named for the president but descended from a separate line of the family, was awarded the Distinguished Flying Cross in 1955 for successfully conducting an emergency landing in California after his C-124 loaded with 79 combat-equipped personnel lost two engines while flying over the Pacific, 300 miles from land.