Classical Liberal asks:
Out of curiosity, what do you see as JFK's foolishness (I don't necessarily disagree, I'm just curious).
JFK was 43 when he was elected president. His view towards the Soviet Union was to not piss them off.
When he came into office, plans were being made for the invasion of Cuba. Kennedy watered those down. For example, he refused air support during the Bay of Pigs. Such a move puzzled Eisenhower who later asked Kennedy for an explanation. He replied that he didn't want to give the Soviet Union a reason to assault Berlin.
When, in fact, the Soviets were pumped up to see the weak initiative of the Americans in taking on Cuba. The Soviets, upon learning of the Bay of Pigs, thought that it would take the Americans easily under a week to defeat that tiny, difficult-to-defend island. They were stunned when America lost in a few days. Kennedy had just showcased to everyone that the leader of the free world was an indecisive buffoon.
Later in the year, Kennedy had meetings with Krushchev where again he displayed weakness. He mentioned how his ambition was to secure peace. He, also, spectacularly admitted that the Soviets had little to fear from the US because US and Soviet-Chinese arsenals were at a parity. This statement was truly remarkable: It was false! The US was far more powerful but Krushchev didn't mind the silly, desperate president's commentary.
The correct strategy would have been to make the Soviets fear the US. The Soviets should have been afraid to piss off the US not the other way around. Kennedy with his actions had taken the edge off deterrence. Kennedy created conditions which made a conflict more, rather than less, likely.
Obama is making similar mistakes. Today, the thugs in the world don't fear the US as much. The US spends billions of dollars on high-tech weaponry. A great example is stealthy submarines which carry missiles with multiple nuclear warheads. Their purpose is to maintain peace -- not to annihilate civilizations. Their purpose is make the thugs think twice, thrice.... before messing with the US and her friends.
Obama thinks that weapons of this nature are obsolete. He thinks that thugs can be reasoned with and told that they have little to fear from America. This is precisely the opposite of a good strategy. It has been tried before multiple times. The payment in blood is always great.