When a President dies in office, steps down or is forced to leave the Oval, the job passes to the next in the line of succession, the Vice-President, until the end of the term. That has been the case since the Constitution was written.

An incumbent with an inherited Presidency running for re-election to the position they were never elected to in the first place and succeeding, though, is something that wouldn’t happen until the 20th Century. We all know that Harry Truman did it and so did LBJ, but it was Theodore Roosevelt in 1904 who broke this particular political ground in 1904.

In 1900, William McKinley won re-election to the Presidency, the first incumbent to do so since Ulysses S. Grant. His first-term VP Garret Hobart had passed away in 1899, so after nixing some of the most likely replacements, McKinley settled on Republican rising star and Governor of New York Theodore Roosevelt.

Despite his popularity, McKinley was shot at the Pan-Am Exhibition in Buffalo, New York in 1901 and died a few days later. Teddy Roosevelt was sworn in as President on September 14th, 1901.

He spent the next three years in office without a Vice-President. Roosevelt made it clear that he would implement McKinley’s policies, the same policies people had voted for.

In addition to that, he made some bold moves, such as inviting African-American community leader Booker T. Washington for dinner at the White House and heavily regulating trusts and prosecuting anti-trust violations through his Attorney General. He became mythologized as the “trust-buster”.

He also successfully cemented his role as the undisputed leader of the Republican Party. Even his longtime enemy and rumored 1904 challenger Mark Hanna was forced to endorse him.

The 1904 Theodore Roosevelt Campaign merch emphasized stability and sought to remind voters that he did what he and McKinley were elected to do. Instead of something catchy like Teddy Roosevelt’s famous quote “Speak softly and carry a big stick” or the official campaign slogan “The Square Deal”, the official campaign poster was kept much more basic.

At the top it read: “Republican policy needs no explanation. Acts and promises fulfilled guarantee the future”. Underneath, there was a picture of the 26th President and underneath that, it simply said “Theodore Roosevelt”.

It clearly worked. Roosevelt, who had inherited the Presidency, was handily re-elected to it. The first person in US history to do it, but certainly not the last.

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The 1948 Presidential Election will be remembered for two things: being one of the biggest upsets in US political history and the famous photograph of incumbent President Harry S. Truman holding up a newspaper announcing his defeat during his victory speech.

Going into the election, it looked like the Democratic Party’s traditional voting base would be split three ways. Upset with the party’s Civil Rights platform, South Carolina Senator Strom Thurmond split with his party to run for President under the right-wing Dixiecrat banner while former Democratic Vice-President Henry A. Wallace challenged the Dems by running on the Progressive Party ticket.

It seemed like the incumbent Democrat was already in trouble. Republican challenger and sitting New York Governor Thomas E. Dewey even avoided mentioning Truman by name as much as possible.

Dewey’s most memorable campaign imagery had the slogan “Keep the Ass Off the White House Grass,, It’s All Dewey” and featured a drawing of the Democrat donkey grazing. While amusing, it cast the Democratic Party establishment as his opponent, rather than Truman and played not only to Republicans but former Democrats on the left and the right mad at party leadership.

On the other hand, Truman hit the ground running, inspiring many with his passionate campaign approach. Meanwhile, the Truman 1948 campaign imagery emphasized the candidate and staying the course, some of it used the slogan “To Secure the Peace“. Very much in line with what an incumbent would do. Except Truman wasn’t a typical incumbent, having ascended to the Presidency when Franklin Delano Roosevelt passed away while in office. This was his first campaign for President.

It turned out that Truman’s approach worked, to the tune of 303 Electoral College votes and 49.6% of the popular vote. The third-party candidates didn’t even get 3% of the popular vote. History will remember this moment as one of the biggest political upsets in US history and also the time a newspaper editor got things so laughably wrong.

You can order 1948 Presidential Election campaign imagery (including the iconic Dewey Defeats Truman photo) printed on hats, t-shirts, mugs, magnets, pins and stickers from Political Retro.

When it comes to political game changers, it’s hard to top the Kennedy-Nixon Debates during the 1960 US Presidential Election. In particular, the first one that aired live from Chicago on Monday, September 26th.

Not only was this the first ever face-to-face Presidential Debate, it was also the first US political debate broadcast on television. Plus, it was the first and last time a candidate would underestimate the importance of TV.

Richard Nixon, the sitting Vice-President, was, according to all the polling, on course to win. He insisted on campaigning right up to a few hours before the debate and refused makeup when he arrived.

He came across as tired, sweaty and old, while his rival, Senator John F. Kennedy, looked young, vibrant and dynamic. The polling changed and Kennedy went on to win the White House.

Here it is, in its entirety:

Visit our shop for original political imagery printed on t-shirts, mugs and pins. We’ve got 1960 JFK Campaign Merch and Richard Nixon Merch from the campaigns he won, either running for President or Vice-President

When Christine O’Donnell ran for a US Senate seat in Delaware in 2010, comedian Bill Maher aired a clip from his old show Politically Incorrect where the now Tea Party-backed Republican candidate admitted to dabbling in witchcraft.

This caused a bit of an uproar, but it was O’Donnell’s response that brought the story to the next level. She started off a campaign ad by looking directly into the camera and saying “I’m not a witch.”

It honestly didn’t matter what she said next. The fact that she felt the scandal was the most important thing to address made it the only thing people talked about. ‘

With people trying to decide if they could believe O’Donnell or if she really was a witch, not enough people were thinking if they wanted her as their Senator or not. She lost the election to Democrat Chris Coons, but entered the bonkers campaign ad hall of fame.