There were no "October" surprises per se in the election of 1796, which was the first contested election. For one thing, presidents were chosen differently. Under the system at the time, each state had an allotted number of electors based on population. (In slaves states, slaves were counted at 3/5 of a person. The electors from each state cast votes for two persons. Both votes were for president and there were no such things as running mates. The candidate who received the most votes became president and the runner-up in the presidential race was elected vice-president. (This would present problems in the election of 1800, when Thomas Jefferson and Aaron Burr received the same number of votes).
By 1796, the government had split into factions or parties, with the Federalists (who believed in a strong central government) being led by Vice-President John Adams, and the Anti-Federalists or Democratic-Republicans led by former Secretary of State Thomas Jefferson. Each party instructed their electors cast one vote for the intended presidential candidate and another vote for somebody else from their party, with the idea that their vice-presidential prospect would receive a few votes shy of their presidential candidate.
Unfortunately, these system had problems. All electoral votes were cast on the same day, and communication between states was only as fast as the fastest horse, making it very difficult to coordinate which electors were to vote for a different vice-president.
At the time, George Washington had just completed two full terms in office. He ran unopposed each time. But Washington had decided that two terms would be enough for him and he refused to run for a third. This made the election of 1796 unique because it was the first contested presidential election in the history of the United States.
John Adams had been the Vice-President in Washington's administration since the birth of the nation. The Vice-Presidency was a largely ceremonial position and Adams did not even attend cabinet meetings. His main duty was to preside over the Senate, and he was often mocked by his political opponents because he was seen as being overly formal and pompous. But Adams was respected by many Federalists for being a leading voice during the Revolution and also because of his commitment to federalism. The Federalists hoped that Thomas Pinckney would be selected as Vice-President. Pinckney had been the Governor of Virginia and he had recently negotiated a treaty with Spain and was on a ship heading home while the election was taking place. . Alexander Hamilton, who had served as Washington's Secretary of the Treasury, felt some animosity towards Adams. Hamilton was unable to run for President because he had been born in the West Indies. Hamilton began working covertly to elect Pinckney over Adams. He tried to convince Jefferson electors from South Carolina to cast their second votes for Pinckney. The scheme ultimately failed, but it increased the subsequent tension between Adams and Hamilton.
The Democratic Republicans selected Thomas Jefferson of Virginia and Aaron Burr of New York as their candidates. Republicans campaigned with the intention that Jefferson would become president.
The campaign was an acrimonious one. Federalists tried to paint their opponents with the violence that was taking place in the French Revolution and said that election Jefferson would bring with it the same kind of violence to the United States. Jefferson and the Republicans accusing the Federalists of favoring a monarchy system and a more aristocratic society. They tried to portray Adams as being too much in favor of Great Britain and a too much in favor of a centralized national government. Adams had the added burden of having Hamilton working to undermine his election.
Jefferson supporters also attacked the Federalists over the Jay Treaty. They sought to tap into anger in the nation among those who believed that the nation did not get enough in its treaty with the British.
While some may believe that attack ads against a candidate personally are a recent phenomenon, they were in fact very present in the election of 1796. Federalists attacked Jefferson, alleging that he was of low moral character, that he was an atheist, and that he was a coward during the War of Independence. Adams supporters also accused Jefferson of being too pro-France. This accusation gained momentum when the French ambassador embarrassed the Republicans by publicly backing Jefferson and attacking the Federalists right before the election.
Jefferson supporters also launched personal attacks on Adams, both for his girth and his pomposity. Benjamin Franklin Bache (the grandson on Benjamin Franklin and the publisher of the pro-Republican newspaper the Aurora) referred to Adams as having "sesquipediality of belly" (an 18 inch long stomach) and for being the "champion of kings, ranks and titles."
Sixteen states chose electors in 1796. In ten states the electors were chosen by the state legislature, while in the other six they were selected by popular vote. Voting took place between Friday November 4 to Wednesday, December 7. Hamilton's efforts to entice southern voters to vote for Pinckney over Adams came to naught. All eight electors in Pinckney's home state of South Carolina, as well as at least one elector in Pennsylvania, cast ballots for both Jefferson and Pinckney. But despite this, at least 20 Adams electors failed to cast their other vote for Pinckney. Adams ended up with more votes than Pinckney, and more votes than Jefferson. If there was any sort of late or October surprise in the election of 1796, it was that Alexander Hamilton's efforts to undermine the election of John Adams and have Charles Pinckney elected instead, were unsuccessful.
The final results gave Adams 71 electoral votes. Jefferson finished second with 68. Pinckney finished third with 59, and Burr was fourth with 30. Nine other candidates received some electoral votes. This meant that Adams was elected President and Jefferson was elected Vice-President. The next four years would be the only time that the president and vice-president were from different parties. Jefferson would use his position as vice-president to attack his president's policies, and this would help him reach the White House in the following election.
On January 6, 1797, Representative William L. Smith of South Carolina presented a resolution on the floor of the House of Representatives for an amendment to the Constitution by which the presidential electors would designate which candidate would be president and which would be vice-president. No action was taken on his proposal and in 1800 this prove to be problematic.