After graduating from Bowdoin College in 1826, he went to
Natchez, Mississippi as a teacher. He continued to study law and was admitted to the bar in 1829. & S. S. Prentiss"
Southern Galaxy, January 28, 1830 In 1832, he moved to
Vicksburg, Mississippi and won a suit involving title to the most valuable part of the city. The property which he obtained as his fee made him one of the wealthiest men of Mississippi. He was elected to the State Legislature in 1835 as a
Whig. He was a slaveholder. In July 1837,
Democrats John F. H. Claiborne and
Samuel J. Gholson were re-elected to the
United States House of Representatives in a
special election. In November 1837, Mississippi held the regular election. Prentiss launched a vigorous, partisan campaign. He and fellow Whig
Thomas J. Word won in an upset. Claiborne and Gholson then argued that the July result entitled them to serve full terms. The House agreed to hear Prentiss. He spoke for nine hours over three days, packing the gallery, drawing Senators, and earning a national reputation for oratory and public admiration from leading Whigs including Senators
Clay and Webster. The Elections Committee then required a
third election. Held in April 1838, it confirmed the November result. Both Whigs were seated in May late in the second session, also serving for the third session. Writing about Prentiss's time in Congress, longtime Washington journalist
Benjamin Perley Poore said that Prentiss was "the most eloquent speaker that I have ever heard":The lame and lisping boy from Maine had ripened, under the Southern sun, into a master orator. The original, ever-varying, and beautiful imagery with which he illustrated and enforced his arguments impressed Webster, Clay,
Everett, and even
John Quincy Adams. But his forte lay in arraigning his political opponents, when his oratory was "terrible as an army with banners;" nothing could stand against the energy of his look, gesture, and impassioned logic, when once he was fairly under way, in denouncing the tricks and selfish cunning of mere party management. The printed reports of his speeches are mere skeletons, which give but a faint idea of them. He served only one term in Congress. Prentiss later went on the lecture circuit. He reportedly rarely gave speeches from prepared notes and, instead, would ad-lib for hours to large crowds that often begged him for more. After Mississippi repudiated her state bonds, Prentiss, who had opposed this action, moved to New Orleans in 1845. He became a leader of the city's bar, and prominent in philanthropic work. Prentiss was publicly embarrassed by his mounting financial troubles. He had made property investments based on disputed land holdings. He was an alcoholic and a gambler. As one history of Vicksburg lawyers put it, "His nights were full of revelry and high conviviality. He drank excessively, lived extravagantly, conversed brilliantly and speculated in real estate. The result was disastrous to his fortunes and he lost all he had accumulated, moved disillusioned to New Orleans and died at forty-two in Natchez in the flaming brilliance of a tragic life." He died at his mother-in-law's house outside Natchez on July 1, 1850, at age 41. His death shocked the nation. Prentiss had been considered among the most gifted young men in the nation. He is buried at Gloucester Plantation Cemetery in Natchez. == Honors and awards ==