Seargent S. Prentiss

THE EARLY childhood home (above) of Seargent S. Prentiss (inset) was in Portland, Maine. Prentiss’ father was a sea captain who operated three ships before the Embargo and Nonimportation Acts during President Thomas Jefferson’s second administration decimated the shipping industry. Ruined financially, the Prentiss family moved 10 miles inland to a farm in Gorham, Maine. (Credit: William Henry Milburn, The Lance, Cross and Canoe: The Flatboat, Rifle and Plough in the Valley of the Mississippi)

"I got on the Sultana at Fort Adams when S. S. Prentiss was aboard on his bridal trip—married that morning at Natchez, and the whole bridal troupe went down to New Orleans,” recalled Dr. A.R. Kilpatrick, a Black River planter in Concordia Parish in a letter years after the event to historian and former Mississippi congressman John F.H. Claiborne. 

 “It was my first sight and acquaintance with Prentiss. I was charmed with his manners and appearance. He had the most handsome head, and it sat better on his neck and shoulders than any person I know. That was in 1843, when his fame was worldwide; yet, sir, he was as bashful, timid and quiet as a boy of 16 in the presence of those ladies. 

“At table he had nothing to say, but ate his meals quietly, almost stealthily. But as soon as he came down in the social hall, he was lively and chatted enough." 

At the time Kilpatrick saw Prentiss aboard the Sultana, the acclaimed trial lawyer, politician and orator was in his mid-30s. For years, it appeared Prentiss would live his life a bachelor. 

Born in Maine where he survived a childhood illness that left his right leg lame, Prentiss has arrived in Natchez at age 19, taught school on two different plantations for more than a year before beginning his career as a lawyer. 

Prentiss was a man of great achievement and great failures. He drank too much and at times lived life recklessly. He gambled at cards and speculated in real estate during an era of speculation. Though his victories were great, his losses were great as well. 

Those who heard him can never forget the strange charm of this wonderful speaker,” wrote Reuben Davis (Recollections of Mississippi and Mississippians), a contemporary of Prentiss’ who was also a lawyer, prosecutor, judge and congressman. “It was like music and poetry, and flame and fire, and love and hate, and memory and aspiration, all bearing away in one swift torrent the souls given up to its enchantment.  

“All his splendid qualities — his brilliant genius, his dauntless courage, his chivalrous honor, his princely generosity, the wonderful gentleness and fascination of his manner — served only to adorn the reckless dissipation and extravagance by which his own life was wrecked, luring others into the same fatal errors. 

“He was the handsomest man I ever saw, his face and head being models of manly beauty. Unfortunately, his right leg was withered by some disease in childhood, and he was morbidly sensitive about this defect, although, by means of a stick … he was able to walk with ease … I have sat at the wine table with him for hours, every one present so captivated by his delightful table-talk that even the wine, of which there was no stint, seemed less intoxicating than his presence.” 




Prentiss’ shyness around girls was legendary. Some believed that due to his limp and lisp that he somehow felt inferior and lacked self-confidence. Yet during his public life women would write him from across the country asking him to visit their towns. 

In a letter home to a friend of the family in Maine, he wrote Mrs. Evelina Pierce about a pretty girl he had met onboard a steamer. The young lady, after reading an article in a newspaper that announced a Frenchman planned to fly a balloon over Niagara Falls, asked aloud if it was true. 

All of the other passengers indicated they didn’t know. 

“At last she applied to me,” Prentiss wrote, “but it was with a kind of desperation, and a look which told that she did not expect much from so insignificant a looking animal as myself.” 

Although he had no idea whether the claim was true, he “told her that it was absolutely a fact – that I had seen the Frenchman in New York.” 

The other men stared at Prentiss “as if to say, in plain English, I lied.” 

But the answer was obviously the right one because the young lady repaid Prentiss “with a smile” so pretty that he determined it “was richly worth forty lies.” 

At Rokeby Plantation in Jefferson County, one of Prentiss’ pupils Joseph Dunbar Shields, quickly observed his teacher’s shyness around women. 

 “The most pleasing and refining safeguard is found in the society of ladies,” Shields wrote (The Life and Times of Seargent Smith Prentiss). “But Prentiss, in his early life in Mississippi, in consequence of his physical infirmity and sensitiveness on account of it, shrunk from the effect of seeking ladies' society. 

“True, his handsome face and fascinating manners could have won his way, but he did not think so, and therefore did not seek it. He had an exalted estimate of the gentler sex; with such a mother and such sisters as he had it could not have been otherwise. But he could not dance attendance upon the ladies on festive occasions and scatter the airy triflings that flitter for a moment in the sunbeams of pleasure, and he was too diffident at other times to obtrude himself upon their society, therefore he was forced to seek relaxation in the society of gentlemen only.” 




Prentiss apparently began to drink in a social way while teaching in Natchez. Shields wrote that while serving as schoolmaster in Jefferson County, Prentiss “was very temperate in his habits. Indeed, so far as I know, his habits were unexceptionable while he was at Natchez. 

“But on one occasion, he joined a party of young men, who rode into the city to dine. As usual, the juice of the grape mingled with the flow of soul, and, before the social, after-dinner converse was over, they all got somewhat merry. Mounting their horses, at rather a late hour, and having twelve miles to ride, they determined to make a dash of it, and thus save time. Now, it so happened that Prentiss was mounted on a horse which had been raised for the turf, but not having fulfilled his destiny, had been degraded to a saddle nag. He retained, however, all the fire of the racing breed … 

“The jolly company started off in full gallop, but had not traveled many hundred paces before Prentiss and Oscar (that was the name of the beast) darted on ahead, and were soon lost in the distance. The rest of the party finding pursuit useless, at length cooled down into a quiet pace, convinced that Oscar and his rider would, after awhile, reappear. But as mile after mile lay behind them, and it was getting very dark, they began to feel somewhat uneasy, when of a sudden, they were hailed by that unmistakable voice, with its peculiar lisp: 

“’Hallo, Boyths! hallo! I say, Oscar has spilled me!’ 

“They approached through the darkness, and found him seated on a bank by the roadside. He had clung to his dare-devil steed as long as he could, and finally with great reluctance, ‘let him travel on alone.’” 




Prentiss, who had scholarly knowledge of the Bible, had always believed in God and was moved during his early life by the piety of his dear mother, whom he credited with saving his life when he was stricken with the disease that almost killed him and left his right leg lame. But he did not share his mother’s unquestionable faith. In a letter to him months after he arrived in Mississippi, she asked about her son’s current state of belief. 

“You ask me, my dear mother, my sentiments on the subject of religion,” he responded. “I hardly know what answer to make you. I cannot pretend to say that I have experienced any change on that subject since I left home. 

“I trust the pious manner in which I was educated, and the excellent examples, which I had in my parents, of the value of religion, will induce me never to look upon it otherwise than with respect and reverence. In all its great principles, I also trust, I have implicit belief. 

“I confess that with regard to what is called conversion, I never well understood it. So far as religion teaches us to do good, and to abstain from evil, I acknowledge its excellence, and hope I am not entirely without its influence; but the distinction of sects, and the necessity of belonging to any one of them, as well as a great many of the abstract articles of belief—considered essential by some denominations, by others not—are all beyond my comprehension. If I am wrong, it is from want of understanding and not from willfulness. 

“Whatever may be my notions on this matter, however, I trust the time will never come when I shall be forgotten in the prayers of my mother.”

(To Be Continued)

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