Yes- Bill Clinton had that honor. in 1968 and 1969.
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No.
the American president who won the Charlemagne prize was Bill Clinton.
One example of a candidate who fits this description is Richard Nixon. He first ran for president in 1960 against John F. Kennedy and lost, then ran again in 1968 and won the election. Nixon served as the 37th President of the United States from 1969 to 1974.
Johnson