The Socialist candidate Eugene V. Debs made four tries at the Office: In 1904 Theodore Roosevelt beat him, in 1908 William Taft won, in 1912 Woodrow Wilson obtained the Office and in 1920 Warren Harding became the President. Debs never won an Electoral Vote.
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Eugene V. Debs ran on the Socialist Party of America ticket five times and never won.
President President
Harold Stassen ran for US president nine times between 1948 and 1992.
When Walter Mondale ran for Vice President in 1976 and 1980, he was Jimmy Carter's running mate. When he ran for President in 1984, his running mate was Geraldine Ferraro (that was the first of two times to date that a woman was one of the major party Vice Presidential candidates).
he was re elected president four times.