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Vicksburg History

The Famed Orator of Vicksburg – S. S. Prentiss



Sargent Prentiss
Sargent Prentiss (Old Courthouse Museum)

Eloquence of speech is a prized tool with immense power. The ability to gather crowds and influence their thoughts with clever language has been coveted all throughout history. Entire nations have risen and fallen with the correct choice of words delivered at the right moment. While some struggle merely writing and delivering a speech, others are granted the gift of gab, allowing them to string together intelligently strategic verse for hours on end. Vicksburg became home to many with a speaking talent. Its proximity to the river brought intellectuals from all across the world to its ports, but none stood in comparison with Sergeant S. Prentiss, the Famed Orator of the South.

Prentiss was only 19 when he came to Mississippi from Maine in 1827. He first arrived in Natchez, taking a position as a teacher, spending any spare time relentlessly studying law in preparation for admission to the bar. Upon becoming licensed to practice law, he set his sights on Vicksburg, as he believed it offered a more inviting field for his particular talents. Soon after getting settled into his new career, it became clear that he was playing the game in a league far above anyone else. His skills as an orator have been described as being almost mystical by spectators, claiming he was “matchless in eloquence that wove a spell of necromancy around the hearts of all who heard him, and brought the willing captives in silent adoration to his feet,” and that his words had “power and witchery” that left others “spellbound, enthralled, hypnotized by an influence which seemed not of this world.”

There were many moments throughout Prentiss’ career in which he undertook the challenge of debate, where his only compensation was the bolstering of his ego from the defeat of his opponent. One such moment that exemplifies his personality and skill came about in November of 1843. Jefferson Davis announced himself as a last-minute candidate for Senate, running as a member of the Democratic Party. Prentiss, not even a candidate for the office but representing the Whig Party, issued a challenge to Davis for the day of the election. On the steps of Court Square, where the Old Court House Museum sits today, the two men would debate in fifteen-minute intervals as citizens entered the building to cast their votes. Being the long-winded orator that Prentiss was, he asked Davis to allow him to extend beyond the fifteen-minute rule on several occasions throughout the day as he had trouble condensing his arguments; Davis agreed so long as Prentiss remained on topic. Prentiss left an impression on Davis that day, later writing about the debate that “he adhered tenaciously to the limitation thus imposed, argues Closely and powerfully, and impressed me more deeply with his capacity for Analysis and logical induction than by any other effort I knew him to make.” Even loyal voters of the Democratic Party could not deny that Prentiss had won the day. The Vicksburg Sentinel, a pro-Democratic publication, wrote, “Mr. Prentiss certainly made the best, and most logical arguments we have ever either heard or read.” Although he had not changed their viewpoints on the subjects that day, he had cemented the victory for the Whig candidate over Davis.

Prentiss Law Office

Prentiss Law Office (Old Courthouse Museum)

His abilities left quite the impression on the people of Warren County despite his career being cut short due to his death in 1850. A portrait of Prentiss was commissioned to hang among the Judges’ in the courtroom of the original courthouse to honor his talents as a lawyer. The portrait avoided the blaze that reduced the courthouse to ash and was moved to the new temple of justice built in 1860, where it is still on display in the courtroom of the Old Court House Museum. Directly behind the Old Court House, his law office still stands on Monroe Street and is considered one of the oldest buildings in the city. In his short time, Prentiss established a new precedent of intellectual excellence for Mississippi and will be remembered as one of the greatest orators throughout history.

Vicksburg and Warren County Historical Society

If you enjoyed this story about Sergeant S. Prentiss and want to learn more, please consider visiting the Old Court House Museum here in Vicksburg, MS. We’ve been a museum for 74 years now, and all items on display were donated by families from here. We also have a vast archive in our McCardle Research Library that is accessible by appointment. Members of the Historical Society have free admission to the museum, so please also consider becoming a member. All proceeds raised through membership go directly to the preservation of the museum and its contents. For more information visit our website at or give us a call at 601-636-0741. You never know what you’ll find at the Old Court House!

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