Theodore Roosevelt in a 1910 Mitchell model S (six cylinder) with Connecticut plate, 1914-1918.
Adam Rifkin stashed this in History Pics
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Reddit comment on who's driving:
Passenger is Theodore Roosevelt Sr. but the driver looks like his son Theodore Roosevelt, Jr. (Assistant Secretary of the Navy, Governor of Puerto Rico, Governor-General of the Philippines, and a Brigadier General in the United States Army. He died in France 36 days after leading the first wave of troops at Utah Beach during the Normandy landings in 1944, an action which earned him the Medal of Honor.)