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Rufus King was the Federalist Party Vice Presidential Nominee in 1804 and 1808 and their Presidential Nominee in 1816. He lost all three elections.

Martin Van Buren was the Democratic Party Vice Presidential Nominee in 1832 and their Presidential Nominee in 1836 and 1840. He won the first two elections and lost the third.

John C. Breckinridge was the Democratic Party Vice Presidential Nominee in 1856 and their southern Presidential Nominee in 1860. He won in 1856 and lost in 1860.

Franklin D. Roosevelt was the Democratic Party Vice Presidential Nominee in 1920 and their Presidential Nominee in 1932, 1936, 1940 and 1944. He won every time except 1920.

Richard M. Nixon was the Republican Party Vice Presidential Nominee in 1952 and 1956 and their Presidential Nominee in 1960, 1968 and 1972. He won every time except 1960.

Hubert H. Humphrey was the Democratic Party Vice Presidential Nominee in 1964 and their Presidential Nominee in 1968. He won in 1964 and lost in 1968.

Walter Mondale was the Democratic Party Vice Presidential Nominee in 1976 and 1980 and their Presidential Nominee in 1984. He won the first election and lost the next two.

George H. W. Bush was the Republican Party Vice Presidential Nominee in 1980 and 1984 and their Presidential Nominee in 1988 and 1992. He won every time except 1992.

Bob Dole was the Republican Party Vice Presidential Nominee in 1976 and their Presidential Nominee in 1996. He lost both elections.

Al Gore was the Democratic Party Vice Presidential Nominee in 1992 and 1996 and their Presidential Nominee in 2000. He won the first two elections and lost the third.

(I did not include John Adams in this list because although he was understood to be a vice presidential candidate in 1788 and 1792, as were several who ran before 1804, officially there were no vice presidential elections before 1804; they were all officially presidential candidates. For those keeping score, Mr. Adams won the Vice Presidency in 1789 and 1792, won the Presidency in 1796, and lost in 1800. Also, although Thomas Jefferson was Vice President when he was elected President in 1800, it was never his intention to run for Vice President. However, he won the Vice Presidency in 1796 because he received more votes for President than John Adams' running mate, Thomas Pinckney.)

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