Dick Chaney ran for Vice President and who is also our Vice President today.
Franklin Roosevelt ran for Vice-President in 1920 . He was the running mate for James Cox. They lost to Harding-Coolidge.
He was first elected president in 1985. He ran for president in 2001, but lost to Alejandro Toledo. In 2006 he ran for president again, and was elected president.
John McCain ran for president twice. He first ran in 2000 and then again in 2008.
He ran for president and won in 1904, then ran again and lost in 1912.
He never ran for President and lost. He did run for the Republican nomination twice without prevailing -- 1968 and 1976.
He lived in a log cabin and was a farm boy. He actually ran for president the first time and lost but then he ran again and won.
This is a guess, probing my "ancient history" files, but it might have been a man named Harold Stassen, who ran for president multiple times.
Walter Mondale lost in a landslide to Reagan in 84.
Richard Nixon is the one who lost to Kennedy in a close election.
Franklin D. Roosevelt ran for vice-president in 1920 but lost. He was elected President in 1932,1936,1940 and 1944.
The incumbent President, William Howard Taft, ran for the Republicans and lost to Wilson in 1912.
George B. McClelland
He ran for president in 1904 and won, and again in 1912, but lost.