- The question is really about the strangest "campaign" — as a whole — in American history as opposed to the strangest thing or things that "happened" during someone's campaign.
Political observers of the past have pointed to:
As I read this article, I started thinking about all the odd elections in American History, Not every election has a character like Ross Perot. Those of us who are old enough to remember Saturday Night Live parodies probably think of Ross Perot more as Dana Carvey than the real Perot. Other than odd characters, ere are a surprisingly large number of elections with unusual results. Here are some off the top of my head: 1801- any consider this election to be the dirtiest in US History. John Adams an Tomas Jefferson made vicious attacks personal attacks against each other and the Federalists went so far as to pass the Alien and Sedition Acts so they could imprison critics of the Federalists and the Adams Administration. The US came close to getting a real scoundrel here. Jefferson should have won easily over John Adams but because of quirks in the Electoral College, Aaron Burr got as many votes resulting in a tie. The election went to the House and Alexander Hamilton threw his influence to Jefferson. Hamilton did not like Jefferson, but he considered him the lesser of two evils, and he was right. Burr was arrested in 1807 on charges of treason for a convoluted plot to try and create a separate western republic in the Louisiana Territory. The trial became a political battle as Federalist John Marshall presided over Burr's trial and acquitted him, largely to put a thumb in Jefferson's eye. Burr got his revenge against Hamilton scandalously shooting him in a duel after Hamilton fired his shot in the air. This election had another side issue. James Callendar published a pro-Jefferson newspaper and was jailed under the Alien and Sedition Act. Jefferson refused to give him a federal post after the election and Callendar publicly wrote about Jefferson's alleged affair with slave Sally Hemmings and the existence of offspring. The scandal has dogged Jefferson ever since (probably for good reason, Hemmings' descendants have Jefferson DNA). 1824- The original populist candidate and hero of New Orleans Andrew Jackson won the popular election and the most electoral votes but the House gave the election to John Quincy Adams. Jackson was outraged and basically began running for the 1828 election right away and won. 1860- The growing slave crisis destroyed the Whig Party in 1852 and events following such as the Kansas-Nebraska Act, Dred Scott, and others destroyed Democrat Party unity by 1860. Former Whigs, Abolitionists and pro business Northerners rallied behind the new Republican Party and its unusual nominee Abraham Lincoln who had lost more elections than he won. The nation split into 4 parties and Lincoln won only 39% of the popular vote but also won a comfortable majority of electoral votes. The election caused the Civil War. 1876- Samuel J. TIlden won the popular vote over Rutherford B. Hayes but a muddled electoral college threw the election to the House. Hayes and the Republicans agreed to end Reconstruction to get the South to support his candidacy. 1912- Teddy Roosevelt ran against his own former vice president and hand picked successor William Taft in a party Roosevelt created called the Bull Moose Party (apt for Roosevelt's personality). Roosevelt only succeeded in dividing the Republican vote which allowed a former college professor and political neophyte Woodrow Wilson to win the election. 1940- Another Roosevelt running for a 3rd term. This time it was Franklin D. Roosevelt who had already served 2 terms. He broke the unofficial precedent set by George Washington in running for a third term. Roosevelt's principled opponent Wendell Willkie who actually assisted FDR because he agreed with FDR's foreign policy and unofficial support of the British in World War II. After the election, Willkie worked for FDR and supported him until his death in 1944. There are others like the election of 1988 with tank riding Michael Dukakis who was quite a character and Gary Hart, the early favorite who was accused of having an affair with Donna Rice and in denying the affair challenged reporters to follow him. They did and caught him meeting Rice to continue the affair. I could go on and on (and already have). If anyone wants to suggest another, feel free to respond.