Obama's Bay of Pigs - NYTimes.com This week, when we are remembering John F. Kennedy, I'd like to touch briefly on the greatest fiasco of his presidency: the Bay of Pigs invasion. No sooner had Kennedy taken the oath of office than he discovered that the Pentagon and C.I.A. were preparing to send 1,500 Cuban exiles to invade Cuba. Though they would be greatly outnumbered by Cuban troops, the American military and the C.I.A. assumed that once the attack began, the Cuban people would rise up and overthrow Fidel Castro. Kennedy was privately skeptical, but he didn't yet have the confidence in his own judgment to override the experts he was surrounded by. So he gave the go-ahead - only to discover that the experts didn't know what they were talking about. The exiles were quickly routed, America was humiliated and Kennedy was left to take the blame. So far, at least, the implementation of the Affordable Care Act has been President Obama's Bay of Pigs. Led to believe that the preparation for Obamacare was on track, Obama was blindsided when that turned out not to be the case. The website where people are supposed to enroll, HealthCare.gov, is a train wreck. People with individual policies saw that they were set to be canceled - and then couldn't enroll in Obamacare because the website had collapsed. In other cases, people discovered that even the least expensive plan available to them under Obamacare cost more than their old plan. And on and on. There are two primary reasons Obamacare has gotten off to such a terrible start. The first is that it is one of the most complicated things that the federal government has ever tried to do; it was inevitable that there would be problems. An insurance executive friend says that the systems Obamacare required were an order of magnitude more complex than even the most complicated insurance company systems. That complexity, says Drew Altman, the president of the Kaiser Family Foundation, was necessitated by the many compromises that were required to pass the bill into law. Ted Marmor, a former Yale professor and an expert on entitlement programs, says that it has to coexist within the extraordinarily complicated "patchwork" that is the American health care system. Marmor was a young special assistant in the old Department of Health, Education and Welfare when Medicare rolled out in 1966 - a rollout that was as smooth as Obamacare's has been rocky. "Our biggest worry was getting Southern hospitals to treat black people," Marmor told me. Partly that was because Medicare was a relatively straightforward program. But Marmor also believes that it was because the men in charge of the new Medicare program were seasoned pros who knew how to get the job done. Thus the second reason the Obamacare rollout has been so awful. "They put amateurs in charge," says Marmor. Obama would have been much better served if, for instance, he had called upon his friend Jeffrey Immelt, the chief executive of General Electric, to choose a team of specialists to lead the effort. To even think that thought, however, requires management skills that this president has never shown. Nor has his initial reaction done much to instill faith. Calling on insurance companies to allow people to keep their old insurance plans - even after they've been canceled - is untenable. Even if state boards of insurance would allow such a move, it still wreaks havoc with the calculations upon which premiums are set. Obama also announced a deadline of Nov. 30 for fixing the problems with HealthCare.gov. But what will that really accomplish? It is an arbitrary deadline that will almost surely not be met - and will sow even more mistrust. With each day's stories about the troubled rollout of Obamacare, it is easy to believe that it is doomed. But it's not - not by a long shot. "We'll know a lot more when we see what the roughly 15 million to 16 million people who are expected to get coverage that first year think," says Altman. And they won't know themselves what they think about Obamacare until they start getting services. Jonathan Gruber, the M.I.T. economist who helped devise the Massachusetts health plan upon which Obamacare is modeled, says the deadline that matters is March 31, 2014. That's when the individual mandate comes into play - meaning that people will either have signed up for health insurance or pay a fine. "It's way too early to panic," he says. Eighteen months after the Bay of Pigs, President Kennedy was confronted with the Cuban missile crisis. Once again, the generals in the Pentagon wanted him to respond militarily, a route that was likely to lead to war with the Soviet Union. But this time, he trusted his own judgment, took a different path and defused the crisis. He had applied the lessons he had learned from the Bay of Pigs to the Cuban missile crisis. As President Obama tries to turn Obamacare around, that is the looming question: Can he learn? Gail Collins is off today.