Robert Trimble (1776-1828) was a Kentucky lawyer and judge whom President John Quincy Adams appointed to the Supreme Court in 1826. His tenure lasted barely two years, but he became one of the Court's most significant dissidents against the broad nationalism of Chief Justice John Marshall. His dissent in Ogden v. Saunders and his majority opinion in Worcester v. Georgia demonstrate a constitutional approach that emphasized the text and original allocation of powers.

Joseph Story (1779-1845) was a Massachusetts lawyer, congressman, professor, legal scholar, and Supreme Court justice. Appointed by President Madison, he served for thirty-three years and wrote influential opinions on federal jurisdiction, contracts, admiralty, commerce, and constitutional structure. His Commentaries on the Constitution became one of the most influential constitutional treatises, combining original meaning with broader principles of national government and natural law.

Richard M. Johnson (1780-1850) was a Kentucky lawyer, soldier, congressman, and senator who gained national prominence during the War of 1812 and later became vice president under Martin Van Buren. Because no vice-presidential candidate received a majority of electoral votes in 1836, the Senate elected Johnson to the office under the Twelfth Amendment. He left office in 1841, returned to Kentucky politics, and died in 1850 without ever becoming president.

John C. Calhoun (1782-1850) was a South Carolina statesman who served in Congress, as secretary of war, and as vice president under both John Quincy Adams and Andrew Jackson. His conflict with Jackson over the tariff and nullification led him to resign the vice presidency in 1832, after which he returned to the Senate and later served as secretary of state. Calhoun became one of the nation's most influential advocates of states' rights and slavery before his death in 1850.

Martin Van Buren (1782-1862) was the eighth President of the United States and a skilled political organizer who helped build the modern Democratic Party. Before becoming president, he served as a U.S. senator, governor of New York, secretary of state, and vice president under Andrew Jackson. His presidency was dominated by the Panic of 1837, and after leaving office he later opposed the expansion of slavery and ran for president as the Free Soil Party's candidate in 1848.

Zachary Taylor (1784-1850) was the 12th President of the United States and a longtime Army officer who became a national hero during the Mexican-American War. As president from 1849 to 1850, he opposed the expansion of slavery into the western territories and supported the admission of California and New Mexico as free states, but his administration was cut short by his sudden death. Taylor's brief presidency came during the growing sectional crisis over slavery.