While there is little expectation that a capitalist rush will soon return the Cuban economy to its prosperous past, there are indications that Raul Castro is initiating subtle changes that could eventually soften the Cuban government’s iron grip on its economy.

Many geopolitical observers see some of the reforms Cuba is promulgating as moves that could one day morph the nation’s economy into a hybrid Chinese model – capitalism, not officially recognized, but not completely stamped out either.

There is already ample speculation as to when and if U.S.-Cuban relations will warm. If Senator McCain takes the White House, the chances of improved relations during his term are slim. If Senator Obama wins the presidency, however, there could be a gradual thaw, and relatively soon at that.

If opportunities for U.S. companies to re-enter the Cuban market emerge, even just as pilot projects, it will be major news – and those companies looking to seize the day will have to be ready to respond to high-profile criticism. Hardliners in Congress may publically question companies’ patriotism. Human rights activists may call for boycotts. Cuban refugee groups could protest at the corporate headquarters. The blogosphere will be alive with chatter. And the list of brand liabilities goes on.

Even though a thawing of U.S.-Cuban relations may be years off, giving some strategic thought to a communications strategy for entry into the Cuban market could be time well invested. It’s never to early to starting preparing for branding issues you can see coming from 90 miles away.