Let's be clear: Castro is a dictator who has used horrific acts to hold onto power, and a democratic Cuba is in the long-term interests of the Cuban people, the United States and the world - that is not up for debate. But whether you agree with Castro's fundamental nationalist message about U.S. imperial ambitions or not, it's clear that he has been effective in using it to keep power. And thus, that begs a very important question: why is the Bush administration walking right into his trap?
In another story, we discover that the administration is now announcing that if Castro dies, "the United States would also send special monitors and advisers to Cuba in the weeks after a full transition began." In the wake of the Vietnam War, which infamously started out with U.S. military "advisers," again - this is clearly fodder that could be easily spun to confirm Castro's own message. And it is especially stupid and destructive to our long-term goals/credibitlity when, at the same time our government is haughtily strutting around making these proclamations, the White House is also saying "it viewed attempts by Venezuela or other countries to influence the transition in Cuba as unwarranted intervention."
In political campaigns, the worst thing a candidate can do is publicly walk into their own stereotype. If, for instance, there are unconfirmed rumors out there that a candidate is a philanderer and is too-slick by half, the worst thing that candidate can do is get caught philandering and then lying about it, because it confirms the negative suspicions the public may have already had. If there are suspicions out there that a candidate waffles or stands for nothing, the worst thing that candidate can do is publicly waffle on a big issue (think John Kerry's "I was for it before I was against it" line on Iraq).
The same thing goes in the situation with Cuba. The stupidest thing American officials can do is publicly walk into Castro's portrayal of our ambitions. By doing that, we are confirming the negative suspicions that many Cubans must have, considering they've been hearing about it over and over and over again for the last 50 years.
As I've written before - Iraq has shown that the definition of "strength" when it comes to national security is not being a politician sitting in a comfortable air-conditioned Washington office and flippantly putting American troops in danger by calling in airstrikes or invasions half way around the globe. Similarly, the situation in Cuba should remind us that "strength" is not a politician puffing out his chest and pigheadedly walking into the very caricatures our enemies have been peddling, so as to potentially alienate indigenous populations that may have otherwise been sympathetic to our goals. That's what's called "weakness" - and the more such weakness is peddled as "strength" by politicians and the media elite, the worse off America will be.