11. Attempting on two separate occasions to defeat the Democratic-Republicans, Charles C. Pinckney was unable to dethrone the ascendancy of Jefferson and his allies
A veteran of the Revolutionary War, Charles Cotesworth Pinckney, along with other members of his immensely powerful and affluent family, represented the interests of the South Carolinian aristocratic elite at the Philadelphia Convention in 1787. Declining to serve in Washington’s administration at first, Pinckney later accepted the position of Minister to France. Gradually identifying with the Federalist Party following his return from the continent, the celebrated general was selected by John Adams as his running mate in his unsuccessful re-election campaign in 1800. With Jefferson immensely popular following the Louisiana Purchase, the Federalists, as a formality, nominated Pinckney as their candidate in 1804.
Not running a serious campaign, believing Jefferson to be unbeatable at that time, Pinckney carried just two states to the incumbent’s fifteen. Selecting Pinckney again in 1808, believing that the winds had shifted and Jeffersonian economic policies were now contestable, the Federalist sought once again to claim the White House. Although performing better than four years earlier, winning five states and forty-seven electoral votes to Madison’s twelve and one-hundred-and-twenty-two, Pinckney failed and Madison became the first individual to succeed a president of his own political party.
10. Contesting the 1952 and 1956 presidential elections, both times against Republican nominee Dwight Eisenhower, Adlai Stevenson got worse rather than better from an already poor starting point
A career government official, Adlai Stevenson rose to political prominence in his capacity as one of the founders of the United Nations in the 1940s. Elected Governor of Illinois in 1948, unseating Republican incumbent Dwight Green by record margins, Stevenson did not immediately set his sights on the White House. With Truman deciding not to seek another term, the outgoing president sought to recruit Stevenson as his replacement. Insisting he was not, nor did he want to be a candidate, Stevenson’s welcoming address at the Democratic National Convention in 1952 was so well received he was forced to nominate himself and subsequently won the candidature on the third ballot.
However, despite appealing to the grassroots of the Democratic Party, Stevenson’s intellectual demeanor failed to impress working-class Democrats and Republicans, who instead turned to war hero Dwight Eisenhower. Despite trying to be a “man for the people, not of them”, Stevenson carried just nine states. Remaining incredibly popular with the party’s base, despite no longer holding political office nor improving his wider appeal, Stevenson was renominated in 1956. Producing an even worse result than before, winning just seven states this time around, Eisenhower increased both his percentage of the vote and number of Electors against his poor Democratic opponent.
9. Splitting the Democratic Party’s core in defense of slavery, John C. Breckinridge ensured the election of the first Republican president and the violent Civil War which would follow the election of 1860
An American lawyer and politician, John Cabell Breckinridge represented the Commonwealth of Kentucky as both a Representative and as a Senator starting in 1851. During this time, Breckinridge established himself in advocating the states’ right position concerning slavery and allying with Stephen Douglas in support of the Kansas-Nebraska Act. Becoming the fourteenth and youngest-ever Vice President in 1857, winning election alongside James Buchanan after being placed on the ticket to balance his northern counterpart, Breckinridge joined with Buchanan in supporting the Lecompton Constitution for Kansas resulting in the split of the Democratic Party in 1859.
Following the walkout of Southern Democrats at the 1860 Democratic National Convention, whereafter the northern and southern factions held rival nominating conventions, Breckinridge was chosen to contest the presidential election on behalf of his tribe. Dividing the Democratic vote, with Breckinridge winning most of the southern states – carrying eleven for seventy-two electoral votes – in failing to make any serious headway into the North due to a split electorate, the stubbornness of the Southern faction resulted in the election of Republican Abraham Lincoln and triggered the Civil War. Following his defeat, Breckinridge ignominiously defected to the Confederacy and was expelled from his seat in the U.S. Senate.
8. One of Franklin Roosevelt’s leading cabinet members, serving for one term as his Vice President, Henry Wallace sought to challenge Truman’s ascendancy in the Democratic Party in the 1948 election
Serving as Secretary of Agriculture, Vice President, and Secretary of Commerce between 1933 and 1946, Henry Agard Wallace was one of the most prominent individuals of Franklin D. Roosevelt’s presidency. Strongly supporting the New Deal, Wallace was rewarded in 1940 when, despite the objections of the conservative wing of the Democratic Party, he was elevated to a place on the victorious Roosevelt ticket. Removed in favor of Harry Truman for the 1944 election, Wallace initially continued to serve following the death of Roosevelt in April 1945. However, in September 1946 Truman fired the longstanding rival for delivering a speech urging conciliatory policies towards the Soviet Union.
Refusing to submit, Wallace and his supporters launched a breakaway party – the Progressive Party – to challenge the Democrats in the 1948 election. Nominating Wallace as their candidate, his campaign was plagued by allegations of communist sympathies and extreme left beliefs. Receiving just 2.4 percent of the popular vote, failing to either defeat or ensure the loss of his replacement, Wallace broke with the Progressives in favor of the Korean War in 1950. Publishing Where I Was Wrong in 1952, Wallace acknowledged his earlier foolhardiness and declared the Soviet Union to be “utterly evil”.
7. Consistently ranked among the worst presidents in American history, Millard Fillmore was dumped by his own party in 1852 before failing to regain the White House in 1856
Becoming Vice President in 1848 following the election of Zachary Taylor, Millard Fillmore rose to the White House after the death of Taylor in July 1950. Instrumental in the passage of the Compromise of 1850, echoing his earlier failures to win either of the Whig nominations for Vice President or Governor of New York in 1844, despite being the sitting executive Fillmore was denied his party’s endorsement in 1852. Largely a result of his enforcement of the Fugitive Slave Act, which remained highly unpopular within certain wings of the party, with the loss of his replacement, Winfield Scott, Fillmore consequently became the last member of the Whig Party to inhabit the Oval Office.
With the breakup of his political party, many of Fillmore’s conservative supporters joined the Know Nothings, transforming the anti-immigration movement into the American Party. Despite not being a member, or ever even attending a gathering of the party, Fillmore was nevertheless nominated as their presidential candidate in 1956. Out of the country when the announcement was made, Fillmore had not been consulted prior to the nomination. Possessing no hostility towards immigration and caring little for nativism, Fillmore instead campaigned on a platform of national unity. Carrying just a single state – Maryland – the Know Nothings quickly faded following their defeat.
6. Running on an extremely conservative platform against President Lyndon Johnson, including opposition to the Civil Rights Act, Republican Barry Goldwater’s efforts to revive segregation in America failed in spectacular fashion
A five-term Senator from Arizona, serving from 1953 to 1965 and again from 1969 to 1987, Barry Goldwater was a Republican politician who sought to lead a conservative revival of American politics in opposition to the progressive leanings of the 1960s. A vocal opponent of the Civil Rights Act of 1964, arguing the legislation represented an overreach of authority by the federal government, Goldwater equally opposed the legacy of the New Deal. Contesting the Republican Party’s nomination against more liberal candidates, such as Nelson Rockefeller, Goldwater successfully mobilized conservative forces and was selected to challenge incumbent Democratic President Lyndon Johnson.
Facing an uphill battle against Johnson, who not only benefited from the martyrdom of Kennedy but favorable economic conditions, Goldwater refused to moderate his policies to broaden his appeal beyond his core supporters. Calling for substantial cuts to social welfare programs, the potential use of nuclear weapons in Vietnam, and the mass privatization of parks and open spaces, Goldwater’s perception as an extremist among the American public was worsened after he became the subject of now-legendary attack ads by the Johnson campaign. Winning just fifty-two electoral votes from six states to Johnson’s four-hundred-and-eighty-six, Goldwater claimed just thirty-eight-and-a-half percent of the popular vote in a landslide defeat.
5. Despite winning his initial election in 1836 in favorable circumstances, Martin Van Buren subsequently lost by a landslide four years later and spent the next eight years fruitlessly trying in various forms to regain the White House
One of the founders of the Democratic Party, after serving as the Governor of New York, Secretary of State, and Vice President under Andrew Jackson, Martin Van Buren was selected as his party’s replacement for the retiring “Hero of New Orleans” in 1836. Winning with the endorsement of the supremely popular Jackson, and aided by divisions within the Whig Party who fielded multiple candidates, Van Buren became the first President to have been born in the United States. Failing to select a nominee for Vice President at the Democratic National Convention, Van Buren contested the 1840 election as the only individual in history from a major party without a running mate.
Losing to a united Whig Party led by William Harrison by 234 to 60 electoral votes, largely as a result of his economic mismanagement, Van Buren sought his party’s nomination four years later to regain his position. However, angering Southerners by his opposition to the annexation of Texas, Van Buren was overlooked. Growing increasingly opposed to slavery, he left the Democratic Party, becoming the presidential nominee for the Free Soil Party in 1848. A single-issue platform opposing the expansion of slavery into the western territories, Van Buren won no electoral votes, but likely stole enough votes from Democratic candidate Lewis Cass to ensure a Whig victory in the election.
4. Offering a poorly received and executed campaign, Walter Mondale’s dire performance in the 1984 presidential election has yet to be replicated by any candidate in the three and a half decades since
Serving in the U.S. Army during the Korean War, Walter Mondale was appointed to fill the vacant seat of Hubert Humphrey as a Senator from Minnesota in 1964 following the latter’s ascendance to the vice presidency. Winning re-election twice, serving from 1964 to 1976, Walter Mondale himself later became the forty-second Vice President of the United States under Jimmy Carter from 1977 to 1981. Defeating several candidates, notably Gary Hart, in the Democratic primaries, Mondale emerged as the party’s nominee against Republican Ronald Reagan in 1984. Campaigning on a platform of tax increases, debt reduction, and a nuclear freeze, Mondale made history in his choice of Geraldine Ferraro as the first female to share a major party’s presidential ticket.
However, becoming one of the most controversial aspects of his campaign, his choice of the unpopular Ferraro under pressure from women’s rights groups quickly rendered a public perception of Mondale as weak and pliable. Failing to resonate with voters, in contrast to the highly skilled and effective Reagan campaign, the Democratic Party’s efforts faltered. Losing just a single state and the District of Columbia – Mondale’s home of Minnesota – Reagan won a landslide victory with five-hundred-and-twenty-five electoral votes, with no candidate in the decades since matching the Republican’s vote share or electoral count.
3. One of the most bizarre occurrences in American political history, the Whig Party put forward four separate and competing presidential tickets in the 1836 election, consequently losing to Democrat Martin Van Buren
Emerging in during the 1834 mid-term elections as the primary opposition to President Jackson and the Democratic Party, formed from members of the National Republican Party, Anti-Masonic Party, as well as the remnants of the Federalist Party and unhappy Democrats supportive of states’ rights, the fledgling Whigs approached the 1836 presidential election in nonsensical fashion. Rather than holding a national nominating convention, instead individual state conventions put forward their own candidates. Proposing four separate individuals – Tennessee Senator Hugh Lawson White, Massachusetts Senator Daniel Webster, South Carolina Senator William Person Mangum, and, by Pennsylvania, General William Henry Harrison – the party remained unable to come to an agreement.
As a result, the Whig Party inexplicably put forward competing tickets in the 1836 presidential election. Despite garnering 48.2 percent of the popular vote collectively, the endeavor was doomed to fail by dividing the spoils between the various candidatures. Whilst Harrison received the most electoral votes, carrying seven states and earning seventy-three electoral votes, White’s campaign took a further twenty-six, Webster fourteen, and Mangum eleven. Although not enough on their own to have won, the Whigs, who would win as a united party in 1840, were destined for failure given their insane strategy.
2. Stealing the nomination from President Chester A. Arthur at an acrimonious nominating convention in 1884, James G. Blaine subsequently lost the election to Democratic Party candidate Grover Cleveland
A charismatic speaker and early supporter of Abraham Lincoln, James Gillespie Blaine represented Maine in the House of Representatives from 1863 to 1876, serving as its Speaker for six years between 1869 and 1875. Serving also in the Senate for a single term from 1876 to 1881, as well as Secretary of State under three separate presidents across two periods, Blaine unsuccessfully sought the Republican nomination in both 1876 and 1880. Becoming the last individual to successfully overcome a sitting president for their party’s nomination, in 1884 Blaine won on the fourth ballot at a fractious nominating convention to dethrone the incumbent President Chester A. Arthur.
Despite entering the election in good standing, Blaine’s image quickly became tarred by accusations of corruption in connection to his prior business involvement with the railroads. Suffering the abandonment of a group of reformist Republicans – the Mugwumps – the dissatisfied collective was comprised chiefly of supporters of President Arthur embittered by their champion’s defeat in the primaries and the ill-grace of Blaine and his supporters in its aftermath. Unable or unwilling to seek to appease the unhappy faction, the group threw their weight behind Democratic candidate Grover Cleveland and Blaine lost the election by 219 to 182 electoral votes.
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.
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