James Madison was born on March 16, 1751 in King George County, Virginia to James and Eleanor (Conway) Madison. He graduated from Princeton in 1771 and served in the continental army during the Revolutionary War. In 1776 he was a member of the Virginia legislature and helped to draft its constitution. He served as delegate to the Continental Congress from 1780 to 1783 and again from 1787 to 1788. He was instrumental in drafting the U.S. Constitution and Bill of Rights in 1787, and then served as a U.S. Representative from Virginia from 1789 to 1797. Madison married Dolly (Payne) Todd on September 15, 1794. He accepted the position of Secretary of State under Jefferson in 1801 and served in that capacity until 1809, when he assumed the duties of the President of the United States. He had been elected in 1808 and was reelected in 1812, serving until 1817. After his second term, he retired to Virginia where he died on June 28, 1836 in Orange County.

Henry Clay was born on April 12, 1777 in Hanover County, Virginia to John and Elizabeth (Hudson) Clay. He married Lucretia Hart on April 11, 1799 and they had several children together. His extensive and varied political career began in 1803 when he was a representative in the Kentucky House of Representatives. He served in the U.S. Senate several times, from 1806 to 1807, from 1810 to 1811, from 1831 to 1842, and from 1849 to 1852. He also served in the U.S. House of Representatives several times, from 1811 to 1814, from 1815 to 1821, and from 1823 to 1825, as Speaker for many of those years. He ran for president in 1824, then served as Secretary of State for John Quincy Adams from 1825 to 1829. Clay died on June 29, 1852 in Washington, DC.

William Harris Crawford was born on February 24, 1772 in Nelson County, Virginia to Joel and Fanny (Harris) Crawford. After studying law privately, he was admitted to the bar in 1799 and began practicing in Lexington, Georgia. He married Susanna Gerardine in 1804 and they had nine children together. Crawford served as a Georgia state representative from 1803 to 1807 when he became a U.S. Senator, serving in that capacity until 1813. He was the minister to France from 1813 to 1815, when he was appointed as Secretary of War for James Madison. After a year in that position, he served as Secretary of the Treasury until 1825. He returned to Georgia and worked as a circuit court judge from 1827 to 1834, when he died on September 15, in Oglethorpe County.

James Monroe was born on April 28, 1758 in Westmoreland County, Virginia to Spence and Elizabeth (Jones) Monroe. He married Eliza Kortright in 1786 and they had two children together. After serving as a colonel in the Revolutionary War, he embarked on a long political career by serving in the Virginia House of Delegates in 1782 and 1786, later returning from 1810 through 1811. In the interim, he was a delegate to the Continental Congress from 1783 to 1786, a U.S. Senator from Virginia from 1790 to 1794, Minister to France from 1794 to 1796 and from 1802 to 1803, governor of Virginia from 1799 to 1802, and minister to Great Britain from 1803 to 1807. After his third term in the House of Delegates, he was again elected as governor of Virginia, but resigned in order to serve as Secretary of State from 1811 to 1817, with interruptions from 1814 to 1815 to be Secretary of War and 1817 to serve his first term as President of the United States. Monroe died on July 4, 1831 in New York City.

Felix Grundy was born on September 11, 1777 in Berkeley County, Virginia. He was admitted to the Kentucky State Bar in 1797 and began practicing in Bardstown. Grundy served in the Kentucky Constitutional Convention in 1799 and went on to serve as a member of the State House of Representatives from 1800 to 1805. He was chosen as Judge of the Kentucky Supreme Court in 1806 and was promoted to Chief Justice in 1807. He soon resigned and moved to Nashville, where he resumed his legal practice before serving in the U.S. House of Representatives (1811-1814) and in the Tennessee House of Representatives (1819-1825). Grundy was elected to the U.S. Senate in 1833 to fill the vacancy caused by John Eaton's resignation. He resigned in 1838 to accept a Cabinet position was appointed Attorney General in July of the same year. He resigned in December of 1839, having been elected to the U.S. Senate to fill the vacancy caused by Ephraim Foster's resignation. Grundy's eligibility was questioned on the grounds that he had been serving as Attorney General at the time of his election, but he was re-elected and served until his death in Nashville, Tennessee on December 19, 1840.