Samuel P. Langely and the Wright Brothers
Samuel P. Langely, who had the full backing of the United States government to invent airplanes, failed miserably. The Wright Brothers, two bicycle salesman with very little backing, were hugely succesful and made the first succesful flight.
World War I
World War I was called "the war that will end war." However, the U.S. got involved in World War II only two decades later and the Korean war only 5 years after the end of World War II.
The Assassination of John F. Kennedy
Prior to his assassination by Lee Harvey Oswald, the Texas Governor's wife said to President John F. Kennedy "Mr. President you can't say that Dallas doesn't love you." Kennedy affirmed her thought: "That's very obvious." Not even an hour later, Kennedy was killed by an assassin in Dallas (assassination is not a loving act in the slighest).
The Beatles
In 1962, the Beatles auditioned for a prominent record producer, who said that the group was "nothing special." Shortly thereafter, they got signed and become the biggest band in the world for years.
9/11 and the Wars in Iraq and Afghanistan
After 9/11, George W. Bush and the United States started wars in both Iraq and Afghanistan with the goal of stopping terrorism and bringing peace and democracy to the region. Instead, there was more terrorism, death, and violence (as well as less democracy) in the two countries.