Stringfellow was born in Fredericksburg, Virginia, on September 3, 1816. He was raised on his father’s plantation and educated in public schools until he was 12 years old when his father sent him to school in Fredericksburg. Later, he attended the University of Virginia at Charlottesville and began to read law in the fall of 1835. He was admitted to the bar and moved to Louisville, Kentucky, before moving again to St. Louis and then to Huntsville, Missouri.
After meeting Sterling Price, he was persuaded to move to Keytesville, Missouri, where he became recognized as a lawyer of ability. Within a short time, he was appointed Circuit Attorney, an office he held for four years. In 1844 he actively entered into political life, was elected to the Missouri State Legislature, and subsequently was appointed Attorney-General of the state, serving four years.
When Kansas Territory was organized in 1854, and the contest over slavery began, an organization called the “Self Defensive Association” was started in Weston, Missouri, of which Stringfellow became the secretary. Foreseeing the coming conflict, he believed the only way to avoid it was by admitting Kansas as a slave state, thus keeping sufficient power in the United States Senate to defeat the abolition movement. He and his brother John organized “blue lodges” along the entire Kansas border. In 1854, along with David Rice Atchison, he attempted to get residents of Southern states to move to Kansas with their slaves to counter those many places settled by the anti-slavery Massachusetts Emigrant Aid Company.
During the winter of 1854-55, he was selected to go to Washington, D.C., to meet the members of Congress from the southern states and explain to them the need for prompt and energetic action. They promised to send slaves to Kansas but failed to do so. Failing to convince southerners to move to Kansas, he issued the “Stringfellow’s Exposition,” which said it was legal for Missourians to vote in Kansas to decide whether it should enter the Union as a free state or a slave state. Stringfellow’s position was reinforced by his title of General in the Missouri Militia and his capacity as publisher of the Squatter Sovereign newspaper. In 1858, Stringfellow went to Memphis, Tennessee, but in the fall of 1859, he became a resident of Atchison, Kansas. At the close of the war, he cordially cooperated with the Republican party and engaged in commercial enterprises, being active in the organization and construction of the first railroads in Kansas. He died on April 26, 1891.