Born on March 31, 1782, in Stonington, Connecticut,[1] Prentiss moved with his family to Worcester, Massachusetts, and then to Northfield, Massachusetts, in 1786, where he completed preparatory studies and was instructed in the classics by private tutor Reverend Samuel C.

[3] In addition to practicing law, Prentiss became active in politics, first as a Federalist,[4] and later as a National Republican[5][6] and Whig.

He was reelected as a Whig in 1837 and served from March 4, 1831, to April 11, 1842, when he resigned to accept a judicial appointment.

[6] While in the Senate, Prentiss was the originator and successful advocate of the law to suppress dueling in the District of Columbia.

He was the second of nine children born to Dr. Samuel Prentiss III and his wife Lucretia (née Holmes).

[8][9] Among the lawyers who received their education and training in Prentiss's office was William Upham, who later served in the United States Senate.