At age 19, Richard Gentry was commissioned as a Lieutenant in the 19th Regiment of the Kentucky Militia and quickly promoted to Captain three years later in 1811.

Gentry hired his personal friend Thomas Hart Benton, the future Senator of Missouri, to be his defense lawyer.

President Martin Van Buren asked Missouri for volunteers in 1837 to help fight against the Seminole tribe in Florida who were resisting Indian Removal.

The women of Columbia stitched a large unit flag for Gentry's troops, which had symbols of the Stars and Stripes and patriotic slogans on it.

[6] On October 15, 1837, Gentry rode out of Columbia with his family physician and friend Dr. William Duncan who made a prophetic observation, "I fear this is our last meeting Richard ...

Richard Gentry and the Missouri Militia assembled at Jefferson Barracks, where Senator Thomas Hart Benton gave them a speech before sending them off.

The Missourians then embarked to Florida and landed at Tampa, where Gentry and his men were put under the command of U.S. Army officer Zachary Taylor.

Richard Gentry and the Missouri Militia were the first U.S. troops sent into battle, as Zachary Taylor ordered them to charge directly at the Seminole position.

[6] Weeks later, in January 1838, the news arrived from Florida that Gentry, age 49, had been killed by the Seminoles at Lake Okeechobee on Christmas Day, 1837.