Mathew Brady (c. 1855-1858). Wikimedia Commons.
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.