Adlai Stevenson
This self-described "egghead" was roundly trounced twice by the same man — war hero General Dwight Eisenhower. Talked into running on the Democratic ticket in 1952 by powerful party leaders, he lost, earning an embarassingly few 89 electoral votes to Eisenhower's 442. In his concession speech, the Unitarian and one-term Illinois governor quoted Abraham Lincoln, saying, "It hurts too much to laugh, but I'm too old to cry." Apparently, he wasn't too old to run again four years later. But the popular Eisenhower was too formidable, and Stevenson lost by an even larger electoral margin than in his first attempt, 73 to 457. Still, Stevenson was a hero to many liberals, who remember him as a candidate who tried to elevate the political dialogue and who lost graciously.
Fortunately for Stevenson, his career in the national spotlight was far from over. John F. Kennedy appointed him chief U.S. representative to the United Nations and he served in this ambassador role until he died in 1965.