SEARGENT S. PRENTISS’S first job in the vicinity of Natchez was on the plantation of Mrs. William Bayard Shield’s along Fairchild’s Creek in Jefferson County, Miss. The plantation home – Rokeby – was located near the Adams County line not far from Church Hill (shown at right center of map). (CreditPanorama of the Mississippi Valley: and Its fortifications, by F.W. Boell. 

With five dollars to his name, 19-year-old Seargent S. Prentiss arrived in Natchez on Friday, November 2, 1827. 

He was in the company of two Natchez planters – Alvarez Fisk and Stephen Duncan. He had met both in Cincinnati where he planned to get his law license but finding no sufficient means to support himself while he studied, he learned from Fisk and Duncan that there were no common schools in Natchez. 

Because of that, the two Natchez men assured Prentiss he would quickly find a job teaching for a local planter’s family. In the meantime, he could study for his law degree. 

In time, Prentiss would become one of the most famous orators in the nation’s history. He would serve in the Mississippi Legislature, in Congress and argue before the U.S. Supreme Court. He would be sought out as a criminal trial lawyer. Newspapers would praise his talents. 

Prentiss had attended Gorham Academy in Maine, graduated from Bowdoin College in Brunswick and studied law in the office of a judge before heading to Cincinnati to make a life for himself. He intended only to stay in the west a year or two before returning home to practice law. 

He worried constantly about his mother, who had been widowed when Prentiss was 16. His father was a sea captain and farmer who died at age 41. 

Seized with a horrendous, stubborn fever when an infant, Prentiss’ childhood was filled with pain and suffering. His mother watched over him like an angel. 

Prentiss’ brother, George, wrote in his book (A Memoir of S.S. Prentiss) that those “who knew him in after years, will, perhaps, recollect his horror at cold water bathing. It had its origin in infancy. After trying in vain all other appliances, his mother was advised to dip him every morning in cold water drawn directly from the well; and this she did, except in the winter, for several years. It proved effectual in hastening his restoration; but he could never after hear of a cold bath without shuddering.” 

For a long period, Prentiss was paralyzed. When he eventually recovered, his right leg was lame. For the rest of his days, he could neither stand nor walk without a cane, but he would live a productive and full life until his death at Longwood in Natchez in 1850. 

Because of his fragile health while growing up, it was feared that at any moment he might die. When his sister Caroline passed away, his father, William, while at sea received word that a child of his was dead. William wrote his wife, Abigail (Prentiss’ mother), assuming it was Seargent who died, lamenting that God took “away the poor cripple, whose prospect for life seemed so hopeless.” 




Instead, Prentiss, who had perfect memory and a fire in his belly to learn, determined at 19 he would go west to seek his fortune. Because the professions were crowded in Maine and the northeast, many headed west – to places like Cincinnati, Ohio – or Natchez and New Orleans in the southwest. 

“How well I remember the scene of bidding us adieu,” brother George wrote of the farewell in Maine, “and going forth in quest of fortune! It was a beautiful afternoon, in the last month of summer; the wagon and Old Gray were at the door; a huge trunk, filled with two years’ outfit, and many a token of maternal and sisterly affection, was in its place; amid numerous tears, the farewell embrace was given … I was just old enough to feel the romance of the scene, without appreciating its import … Indeed, if I were now to witness one quietly departing for the moon, it could hardly appear so wonderful as his setting out for the Far West then seemed to me.” 

During his short stay in Cincinnati, Prentiss studied in the law office of Judge Nathaniel Wright. Wright saw greatness in Prentiss and encouraged him to go Natchez where he had “no doubt he would find employment there for the time being … Yankees of talents and integrity generally succeed there.” 

In Prentiss, the judge saw a young man “very studious, sociable and pleasant; showing clearness and quickness of mind, and great command of the language, for one so young.” But Wright feared that Prentiss lacked confidence, a possible weakness in places like Natchez where men risked it all for fortune. 




After checking in at the Mansion House in Natchez, Prentiss put the word out that he was seeking a teaching position. Twenty days later, he found a job. 

On Nov. 21, he wrote his other brother, William, that he had “obtained a situation. It is in the family of a widow lady, who lives about twelve miles from here, in the country. She has five children, whom I shall teach. It is said to be one of the most respectable families in the country. The lady, too, I understand, is very pious, which will suit mother exactly. Her name is Shields. 

“The great advantage of the situation is, that Mrs. Shields has in her house one of the finest law-libraries in the State – her husband {William Bayard Shields} having been formerly Judge of the Supreme Court. I am to have the entire use of this library; so that I shall be in as good a situation for pursuing my studies, as if I were in a lawyer’s office. I made the engagement yesterday, and to-morrow shall go out to stay.” 

The location of the plantation was near Church Hill in Jefferson County. One of the five Shields children Prentiss was to teach was Joseph Dunbar Shields. The other children ranged in age from 6 to 18. 

Shields wrote a book on Prentiss (The Life & Times of Seargent Smith Prentiss) and recalled: 

“Just twelve miles northeast of Natchez, on a little creek, called Fairchild's, the southwestern boundary of Jefferson County, there stands an unpretending country residence … The house stood on the crown of the hill, and was a rural pleasant home. 

“The plantation was opened about the time that Walter Scott was delighting the literary world with his poems, and the owners named it after the poem issued on the last day of December, 1812,—‘Rokeby.’ … On the 20th of November, hearing that Mrs. Shields wanted a private teacher for her children, he (Prentiss) rode out to ‘Rokeby,’ and there for the first time met the family. Fortified with letters of recommendation he introduced himself, and presented them to my mother. 

“Like all others who saw him, she was struck with his modest deportment and pleasing address … The arrangement with Mrs. Shields was soon made. He was to teach her five children for his board and three hundred dollars, with the privilege of getting other scholars from the neighborhood, and, to him, the inestimable privilege of the use of the law library; besides this, whenever he chose, he was to have the use of horse and saddle for recreation … The engagement being settled, Prentiss took his leave, to return in a day or two to take charge of the school. I remember seeing him, as he left, how he led his horse up to the horse-block to mount, and how he rode away.” 




Two days before Christmas, a homesick Prentiss wrote his beloved mother with the news: “If I could run over a couple of a thousand miles in the course of an evening, you would likely see me amongst you two or three times a week, at least.” 

A few weeks later he wrote again: 

“My Dear Mother: I again sit down to the pleasant task of writing to you – and, for a little while, shall almost imagine myself at home. Indeed it requires very little stretch of the imagination to carry me back amongst you; and often when I awake in the morning, I expect to hear you calling me to breakfast – forgetting that I am two thousand miles beyond the reach of your voice.” 

(To Be Continued) 

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