20 Ill-Fated Powerful Men in U.S. History

1. Attempting to win a presidential election on three separate occasions, Henry Clay failed in 1824, 1832, and 1844, representing different parties on each flawed effort

Representing Kentucky in both the United States Senate and House of Representatives, interrupting these positions with a single term as Secretary of State from 1825 and 1829, Henry Clay Sr. was a widely celebrated politician of his age. Chosen as Speaker of the House on three separate occasions, holding the title for a combined total of ten years, his capacity for mediation and defusing crises earned him the affable moniker of “Great Compromiser”. Finishing fourth on his first attempt to become president in 1824, carrying only three states and winning thirty-seven electoral votes, it has been alleged Clay’s support for John Quincy Adams during the resultant contingent election in the House was won as part of a “corrupt bargain” for his subsequent cabinet position.

Running against Jackson in the 1832 presidential election as the National Republican candidate, although performing marginally better among an equally crowded four-way slate, Clay likewise lost. Claiming just six states and forty-nine electoral votes, Clay, however, was not to be dissuaded. Trying for a final time in 1844, Clay successfully won the Whig nomination in the absence of John Tyler, meeting Democratic nominee James K. Polk in the general election. Offering his best performance, albeit not enough, Clay lost by 170 to 105 electoral votes, winning eleven states to Polk’s fifteen.

Where do we find this stuff? Here are our sources:

“Rufus King: American Federalist”, Robert Ernst, University of North Carolina Press (1968)

“Harry Truman’s Improbable Victory and the Year that Changed America”, David Pietrusza, Union Square Press (2011)

“Truman Defeats Dewey”, Gary A. Donaldson, University of Kentucky Press (2000)

“We Almost Made It”, Malcolm D. MacDougall, Crown Publishing (1977)

“Presidential Elections, 1789-2008: County, State, and National Mapping of Election Data”, Donald Richard Deskins, Hanes Walton, and Sherman Puckett, University of Michigan Press (2010)

“Encyclopaedia of American Political Parties and Elections”, Larry Sabato and Howard Ernst, Infobase Publishing (2007)

“The Rise and Fall of the American Whig Party: Jacksonian Politics and the Onset of the Civil War”, Michael F. Holt, Oxford University Press (1999)

“Presidential Also-Rans and Running Mates: 1788 Through 1996”, Leslie Southwick, McFarland Publishing (1998)

“Truman’s Triumphs: The 1948 Election and the Making of Postwar America”, Andrew E. Busch, University of Kansas Press (2012)

Harry Truman and the Election of 1948: The Coming of Age of Civil Rights in American Politics”, Harvard Stitkoff, Journal of Southern History (November 1971)

“Horace Greeley and the Politicians: The Liberal Republican Convention in 1872”, Matthew T. Downey, The Journal of American History (March 1967)