Grimes was a steamboat pilot on the upper Mississippi river at the outbreak of the war. Refusing to take the oath of allegiance to the United States suddenly required to renew pilot’s licenses, Grimes left the river and waited, expecting that in a few weeks the “secession disturbance would be settled.” Grimes’ own family was Union, his mother saying she had to leave her home in Ralls County because of the animosity of her pro-secession neighbors to her views. At least one of Grimes’ brothers enlisted in the Union army. Many others of his relatives, aunts and cousins, aided him in his mail smuggling at great personal risk and cost. The family of his fiancée, Lucy Glascock, was also pro-Confederate. Their wartime romance become famous.
Grimes first joined an irregular Missouri State Guard unit in Ralls County, Missouri. Sam Clemens, later famous as author Mark Twain, was a lieutenant in the “Ralls County Rangers.” Twain’s version of the adventures of this unit leans more to the serious side than the version Grimes told. (these hyperlinks take you to another site–use your back button to return here). A Twain biographer gives more credence for accuracy to Grimes’ version. Grimes later joined the 1st Missouri Cavalry CSA as a private and was captured near Springfield, Missouri. He escaped while being sent from Myrtle Street Prison in St. Louis to Alton Prison in Illinois.
Before returning south to join his unit, Grimes decided to gather up letters from Missouri families to carry with him, thus establishing himself in his wartime career, becoming “Official Confederate Mail Carrier”, with a commission as a major, for General Sterling Price’s army. Grimes was captured several times but acquired a reputation as an escape artist, once by escaping from the guardhouse at Cairo, Illinois, then from Gratiot Street Prison in St. Louis while chained in close confinement and under heavy guard.
(this hyperlink takes you to another site–use your back button to return here–the site has very loud music on it, you may wish to mute your audio before following the link)
The next time the Federals arrested him they were very serious about holding on to him and several escape attempts failed.
In the last attempt to escape from Gratiot in June of 1864, shortly before Grimes was scheduled to be hanged as a Rebel spy, two men were killed and Grimes was shot and seriously injured. This ended both his escape attempts and wartime career. Grimes was spared execution through the influence of Union friends, eventually being given a full pardon by President Lincoln.
Grimes married Lucy Glascock in March of 1865. They had seven children together but only two–Hudson D. Grimes and Lottie Grimes Mitchell–survived to adulthood. Grimes returned to river piloting, then into other careers, including the ownership of a hotel. He also owned a hunting resort in Lincoln County, Missouri. A few years after Lucy’s death in 1903, Grimes remarried to a younger woman named Nell Tauke. Grimes died in March of 1911.
Shortly before his death, at daughter Lottie’s insistence, Grimes wrote his memoirs. It’s likely he never intended the memoirs to see publication, and they weren’t published until 1926. The story he tells is true, though contains many errors in dating and sequence of events, but also contains considerable omissions. Grimes was far more deeply associated with the Confederate secret service agents operating under General Price than he says in his book. Still, the book is a fascinating story of the War in Missouri and along the Mississippi River.