A head of George Washington, the first President of the United States, facing left.

Designer: John Flanagan (JF), 1932 version from a 1786 bust by Houdon / William Cousins.

Depicts a young Theodore Roosevelt on horseback surveying the terrain near the Little Missouri River.

Theodore "Teddy" Roosevelt (1858 – 1919), often referred to as TR, was an American statesman, author, explorer, soldier, naturalist, and reformer who served as the 26th President of the United States from 1901 to 1909. As a leader of the Republican Party during this time, he became a driving force for the Progressive Era in the United States in the early 20th Century.

Roosevelt built a second ranch named Elk Horn, thirty-five miles (56 km) north of the boomtown of Medora, North Dakota. On the banks of the Little Missouri, Roosevelt learned to ride western style, rope and hunt; though he earned the respect of the authentic cowboys, they were not overly impressed. He reoriented, and began writing about frontier life for national magazines; he also published three books – Hunting Trips of a Ranchman, Ranch Life and the Hunting-Trail, and The Wilderness Hunter.

Designer: Joel Iskowitz (JI)
Engraver: Phebe Hemphill (PH)