Over the course of our nation’s history, hundreds of determined candidates have taken aim at the Oval Office. On this week’s episode of Join or Die with Craig Ferguson, HISTORY’s late-night host and his celebrity panelists will take a look back at candidates who not only struggled to find support, but missed the mark entirely. Read on for more of the longest of long shots in the fight for the presidency. 

7. VICTORIA WOODHULL, 1872

Victoria Woodhull’s biggest mistake was being about a century and a half ahead of her time. After amassing small personal fortunes as Wall Street speculators, she and her sister Tennessee Claflin founded an activist journal called Woodhull and Claflin’s Weekly in 1870. Later on, it became the first American journal to publish Karl Marx’s Communist Manifesto

Over the course of her life, Woodhull fervently promoted such causes as women’s suffrage and sex education. Today, however, she’s primarily remembered for her remarkable White House bid. 

In 1872—47 years before American women won the right to vote—Woodhull became the first female presidential candidate in U.S. history. Nominated by the Equal Rights party (which she’d helped found), Woodhull used her campaign to promote such causes as an eight-hour workday and abolishing the death penalty. 

Unfortunately, the number of votes that she received was never recorded. We do, however, know Woodhull’s election day whereabouts. Accused of distributing obscene material by mail, she and her sister were imprisoned on November 2. Later found “not guilty,” they were released the following month.

6. JAMES B. WEAVER, 1892

Dissatisfied with the two major parties, American farmers responded by creating one of their own in 1892. Known as the Populist or “People’s” party, it opposed monopolies, supported the nationalization of American railroads, and advocated for more robust corporate regulations. 

In 1892, their candidate for the country’s highest office was one James B. Weaver, a decorated Civil War veteran and former congressman. Ultimately, he won more than 1 million popular votes—enough for a distant third-place finish behind Republican Benjamin Harrison and the victorious Democrat Grover Cleveland. After sending several other candidates to congress, the Populists merged with the Democratic party four years later. 

5. JOHN C. BRECKINRIDGE, 1860

Between 1857 and 1861, Breckinridge served as vice president under fellow Democrat James Buchanan. In 1860, the Kentuckian saw his party splinter over the issue of slavery. During that pivotal year, two competing Democratic National Conventions were held in Baltimore. Breckinridge was eventually selected as the nominee of the party’s vocal Southern faction. 

Central to his platform was the belief that slavery couldn’t be barred or restricted in any government territory. This put him at odds with Stephen A. Douglas, who felt that the territories themselves could outright ban it if they pleased. Douglas became the candidate of choice for northern Democrats. Meanwhile, third-party candidate John Bell and Republican Abraham Lincoln also threw their hats into the crowded ring. 

Had the Democrats been unified, they may well have retained the White House. Instead, Lincoln nabbed it with 180 electoral votes (none of which came from Southern states.) 

4. DANIEL WEBSTER, HUGH LAWSON, AND WILLIAM HENRY HARRISON, 1836

As we’ve seen, things generally don’t end well for political parties that field multiple candidates in the same election. Yet, in 1836, the Whigs did so on purpose. 

It was a weird strategy to say the least. Against Democrat Martin Van Buren, the Whigs backed not one, not two, but three presidential nominees: Hugh Lawson White of Tennessee, William Henry Harrison of Ohio, and Daniel Webster of Massachusetts.

What exactly was the plan here? Basically, the Whigs were hoping for a repeat of the 1824 debacle. If all went well, their three candidates would collectively win enough votes to deny Van Buren an electoral college majority. Then, the House—which happened to be Whig-controlled at the time—would again step in and select a new president. Alas, this didn’t quite work out. Instead, Van Buren singlehandedly took home more electoral votes than the other three men put together.

3. WILLIAM WIRT, 1832

The 1820s and 1830s weren’t a great time to be a Freemason. During this period, widespread hostility towards the secretive organization culminated in the birth of a national Anti-Masonic party. In 1832, former Attorney General William Wirt ran for president as neither a Democratic-Republican nor a Whig, but as an Anti-Mason. In the election, his candidacy might have been a complete non-factor—if he hadn’t managed to carry Vermont’s seven electoral votes.

2. MARTIN VAN BUREN, 1848

Poor economic policies cost incumbent President Martin Van Buren dearly during his 1840 re-election bid. Having earned the nickname “Martin Van Ruin,” he lost to Whig candidate William Henry Harrison by 174 electoral votes. 

Four years later, Van Buren was at it again. This time, however, he couldn’t even land his own party’s nomination, which instead went to expansionist and one-term wonder James K. Polk. Undaunted, Van Buren tried running on a different ticket in 1848. As a longtime opponent of slavery, he was deemed a perfect candidate for the Free Soil Party—an upstart group of Democrats who wished to prohibit the practice in all new U.S. territories. Van Buren gladly championed their cause. 

Though the former president didn’t secure a single electoral vote in doing so, he maintained a good attitude about the whole thing. The Free Soilers, he later opined, had triumphantly “accomplished… more than we had any right to expect.”

1. JOHN QUINCY ADAMS, 1828

Adams won the presidency in 1824 in a controversial fashion. Four major candidates went head-to-head, with Andrew Jackson securing the most electoral votes by a sizable margin. However, because neither he nor any of his opponents had earned enough to claim a majority (in terms of total votes cast), the winner was chosen by the House of Representatives. Victory then went to Adams—leading Jackson to cry foul.

Over the next four years, he’d paint himself as a rugged people’s man and his political enemies as nothing but corrupt elites. Taking advantage of his nickname, “Old Hickory,” Jackson doubled-down on his personal branding efforts by doling out hickory wood products (toothpicks, canes, etc.) on campaign stops. Jackson’s visible grassroots coalition triggered a massive voter turnout which more than doubled that of 1824. This time around, his hard work paid off: Jackson routed Adams by a whopping 95 votes in the electoral college.

Catch a new Join or Die with Craig Ferguson this Thursday at 11/10c on HISTORY. Disagree with our ranking? Click here to see a different take on hopeless presidential campaigns.