You could ask President Kennedy some questions relating to his religion. For example, you might ask him why he thinks Americans were finally able to accept a Catholic President in 1960. You might also ask him if being the first Catholic American President hindered him in anyway during his presidency.
You could also ask him about the 1960 Presidential Election. The 1960 election was one of the closest presidential elections in American history, so you could ask him what he thinks finally swung the election in his favor. In addition, there is some doubt over the legitimacy over the 1960 election, particularly over the votes in the state of Illinois. You could ask him he could shed some light on what some have called voter fraud.
You might also want to ask him some questions pertaining to the civil rights movement. JFK took a cautious approach to the civil rights...
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movement initially. You could ask him why he took this approach at the beginning and what the catalyst was that changed his mind. Additionally, because black Americans are still fighting for their rights, you could ask if he thinks civil rights went far enough and what other changes he thinks could have been made to improve the lives of African Americans.
During the Vietnam war, JFK was a big advocate for US involvement in Vietnam from the mid fifties. You could ask him why this was and if he regrets it. Additionally, you could ask him how different he thinks it would have been in Vietnam if he had continued as president.
JFK was also president during the Cuban Missile Crisis. Did he have plans in place to deal with a nuclear attack? If so, what were they? How would he have protected the American people? What was his relationship with Khrushchev? How did he manage to work together to deescalate the conflict?
To wrap things up, you could ask him what changes he would like to make today if he were still president.
References
The world might be a very different place if John F. Kennedy had survived his 1963 assassination. Stephen King has written an interesting and entertaining novel about that subject. The book, 11/22/63, is about a man who goes back in time and kills Oswald before the fatal shot. King's prediction, however, is that the world went totally out of control because Kennedy lived. Of course, King's forecast has more to do with what happens when the past is changed than any condemnation of Kennedy.
Anyway, if I were to ask JFK ten questions, some might involve events that happened in the aftermath of his death and some about more recent history. These ten questions are in no particular order as to importance.
1. Mr. President, you wrote an excellent book called Profiles in Courage about American senators who displayed great bravery or integrity in the service of the country. If you were to rewrite the book and only include senators from the last 60 years, who might they be?
2. The Revenue Act of 1964 (which you originally campaigned for and supported although it was passed after your death) cut the top tax rate from 91% to 65%. Today the top tax rate is 39%. Do you think this is a positive or a negative for the country?
3. You were the first president to have a poet read at the inaugural address. It was Robert Frost, who is considered one of the greatest poets in American history. The tradition has been carried on by recent presidents. If you were to be inaugurated in 2016, which living poet might you choose to read?
4. OK, here's the big question I'm sure you've been waiting for. If you had been alive in August of 1964 when the USS Maddox was attacked by North Vietnamese ships in the Gulf of Tonkin, what would have been your immediate response? Do you agree that Johnson did the right thing in escalating the American presence in Vietnam, or was he wrong?
5. Here's another question about Johnson. Would you have favored Johnson's war on poverty? It has been much debated in the last several years. Some say it worked, but most conservatives say it led to more problems. What would you have done differently to help the poor in America?
6. If you had been alive in 1968, just finishing your second term as president, would you have encouraged your brother Robert to run for president?
7. On a similar note, what do you think of the fact that, like the Kennedy's, the Bush's and Clintons seem to be always present in the run for president? In fact, either a Clinton or a Bush has run for president in every election (except 1984 and 2012) since 1980.
8. Your favorite poem was "Stopping by Woods on a Snowy Evening." One line of the poem reads,
But I have promises to keep,
And miles to go before I sleep