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Franklin Roosevelt was the only one who was elected three times or more.

Grover Cleveland ran as a Democrat three times and won two times.

Thomas Jefferson and Andrew Jackson came in second the first time they ran and then won the next two times. Neither actually ran , in the modern sense of a campaign, the first time that they received electoral votes.

William Jennings Bryan ran three times for the Democrats and lost three times.

Henry Clay was a candidate one time before national parties were formed and then ran two more times as the Whig candidate.

Martin Van Buren ran for a third time on the minor Free Soil ticket.

Several minor party candidates ran three or more times. Norman Thomas and Eugene Debs, for example, were perennial third party candidates.

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