Unlike JFK, Barack Obama's defining moment has arrived, not in the clarity of going eyeball-to-eyeball with a foreign power over nuclear weapons but head to head with Congress in a muddled confrontation he failed to anticipate sufficiently or control.
No matter how incredibly unfair it may be to compare the Cuban Missile Crisis to today's impasse over health care, presidents don't get to choose what will test them. The nature of their response is what counts.
Both Kennedy and Obama came into office with youthful energy and promises of change. In a calmer time, JFK immediately tripped over the Bay of Pigs disaster, took full responsibility and learned the limits of presidential power and the need to prepare the public for decisive actions.
Obama, on the other hand, beset by multiple crises, has not had the luxury of such on-the-job training. He has been forced into finger-in-the dike actions of economic stimulus, auto industry rescues and bank bailouts in the face of solid opposition from Congressional Republicans, using his trademark eloquence to paper over differences as well as he can.
What can be counted against him is the failure to learn from all this that mounting a massive overhaul of health care, no matter how urgently needed, would require a well-defined proposal and a period of public education to have any success against the inevitable lobbying of health insurers, providers and their legislative lackeys.
In this, Obama failed to benefit not only from the experience of John F. Kennedy but Bill Clinton, whose 1990s failure predicted what would happen. Instead of offering firm leadership, this President unwisely deferred to Congress, courted an intransigent GOP and allowed reform to balloon into an unholy mess of compromises, side deals and sellouts.
Now, he is in crisis, at least partly of his own making, as he prepares yet another speech tomorrow on "the way forward" to reconciling and passing what never should have arrived at his desk in the grotesque form that it inevitably will, no matter how many fixes are negotiated between now and then.
It is too late now to start from scratch, so the President will have to take the advice of Warren Buffett, who has a bigger financial stake in America than anyone else, and "get rid of the nonsense" in the Senate and House versions and retain what will stop feeding "the tapeworm that's eating at American competitiveness."
As a transformative figure, Barack Obama is at a crossroads where he will have to show us what he has learned about leadership.