The European war resulting from the French Revolution led many Federalists and other citizens to plead for Washington to accept a third term. He finally refused and announced his retirement on 17 September 1796 in the farewell address. As vice president for eight years and the man who had twice received the second-highest electoral vote, Adams was obviously the heir apparent. But unlike the elections of Washington, this time there was a contest. James Madison, leader of the opposition party in Congress—the Republicans—pushed the candidacy of Thomas Jefferson, to save, so he believed, the country from the aristocratic principles of the Federalists. Although increasingly fearful of Hamilton, Jefferson proved to be such a reluctant candidate that he advised Madison to favor Adams in case of a tie, for the vice president had always been, in Jefferson's words, "my senior." As much as he craved elevation to the first position, Adams' principles would not let him campaign for the office; electioneering was left to others.
As usual, Hamilton sought to play kingmaker. He understood that Adams was too popular in New England to be openly pushed aside, and he regarded Jefferson as the greater evil of the two candidates. But he saw in the electoral college the possibility of electing a Federalist president, who would be more likely to follow his leadership than Adams. Each elector was required to cast two ballots without designating which was for president and which for vice president. Hamilton advanced the vice presidential candidacy of Thomas Pinckney of South Carolina, who had concluded the popular Pinckney Treaty of 1795 with Spain. If New England divided its votes between the two and the South cast a solid vote for Pinckney while scattering its second ballots, the southerner might come in ahead of Adams.
Hamilton's strategy backfired. It produced confusion among Federalist leaders and resentment in New England, whose electors withheld some votes from Pinckney. When the ballots were opened in the Senate on 8 February 1797, John Adams performed his vice presidential duty of announcing his own election. He had received seventy-one votes, Jefferson sixty-eight, and Pinckney fifty-nine. The nation had chosen a president and vice president of opposite parties. More ominous was the sectional nature of the results. Adams had won only thirteen votes south of New Jersey, and seven of these had come from the single state of Maryland. Jefferson had received none north of Pennsylvania.