Kennedy vs. Nixon: 1960

Richard Nixon should have won in 1960. He was clearly the most qualified candidate while his opponent had a thin congressional resume. However, circumstances and modernity worked against Richard Nixon. With a couple of breaks, some pure luck, and some pure skill, JFK eeked out a narrow victory.
Ike had to step down after two terms. Had he been able to run in 1960, he would have beaten anyone the Dems could throw at him. Ike's Vice President, Richard Nixon, promised to continue Ike's policies and touted his experience as the G.O.P. overwhelmingly nominated him for president.
The Democrats had about a dozen candidates. The one that finally emerged was John F. Kennedy. Many Democrats including Harry Truman thought Kennedy was too inexperience to be president. However, his father's connections combined with Kennedy's charisma and media savvy won the day. It turned out JFK's biggest problem was not experience, but his religion. The last Catholic candidate was Al Smith in 1928 and he was crushed.
Nixon did not want to touch Kennedy's Catholicism. He felt it was bigoted to do so. Instead, he hammered home the experience issue. Experience never seems to help a candidate when they raise it as an issue. Nixon held a slight lead through much of the campaign.
Then, Nixon got sick. He lost some time on the campaign trail allowing Kennedy to do some catchup work.. Additionally, Nixon promised to visit all 50 states which took time from his schedule when he could have been hitting battleground states. Then, President Eisenhower got sick. Despite this, he offered to campaign for Nixon. The V.P. refused fearing it might kill the general.
What killed Nixon's campaign was the first TV debate with Kennedy. Nixon was recovering from his illness and looked gaunt. On top of this, he refused to wear makeup and did not shave. This accentuated his Richard III-esque features. On the other hand, Kennedy was tanned, clean shaven, and had visited a hooker before the debate...thus relaxing him. Those watching on TV believed Kennedy won the debate while those listening on the radio believed Nixon won. Ironically, Nixon was the first politician to effectively use television during his "Checkers" speech in 1952.
When election day rolled around, Kennedy squeaked out a victory. After some research, some historians have concluded that Nixon actually won the election. There was vote fraud in Illinois and Texas. In response to dead voters voting Democratic, LBJ quipped, "That's how they would have voted!" In Illinois, Chicago is notorious for vote fraud and that specter showed it's ugly head again during the 2008 Democratic Primaries. The history of Democratic vote fraud also explains Republican howls during the 2000 election.
Lastly, the 1960 election is the time African-Americans turned overwhelmingly Democrat. From 1865-1932, they were overwhelmingly Republican. The Depression turned them into a swing vote. Despite the fact Democrats sponsored segregation and Republicans desegregated Little Rock, passed two Civil Rights bills under Ike, and a Republican Supreme Court Justice authored Brown v. Board, JFK mesmerized them. The key moment came during the sit-ins. Martin Luther King was arrested and his wife feared for his life. While Nixon went to Justice behind the scenes to try and get him released, Bobby Kennedy used public pressure to secure King's release. King endorsed Kennedy and the black vote has been Democratic ever since.
JFK became president, did an effective job, and was then assassinated and turned into a martyr.