Alliances among America’s enemies have been accelerating at an unprecedented rate. As reported by FrontPage throughout this year, Russia, Cuba and Venezuela have recently signed numerous economic and military agreements. Now, at the end of this month, the three nations are gathering once again for a series of historic meetings.

Raul Castro is scheduled to make his first visit to Venezuela since becoming the new President of Cuba after his elderly brother Fidel stepped aside earlier this year. The event is expected to take place in Caracas on November 26, and will involve the Bolivarian Alternative for the Americas (ALBA), an international cooperation organization in Latin America and the Caribbean, and Petrocaribe, a Caribbean oil alliance. Venezuelan President Hugo Chavez has long hoped to hold a summit dedicated to tackling the ongoing financial crisis, an event he has said would be an alternative to the recent G20 summit in Washington.

That same week, Russian President Dmitry Medvedev will visit Brazil, Venezuela and Cuba following the Asia-Pacific Economic Cooperation (APEC) summit in Peru.

The timing of these summits is no coincidence. “Viewing the transfer of power between U.S. President George W. Bush and President-elect Barack Obama as a key transition period,” say Stratfor analysts, Medvedev’s “intent is to remind the incoming U.S. president that [Medvedev] too can play in another power’s near abroad.”

The same thinking motivates Castro and Chavez as well – they need to “lay out the chessboard for the incoming U.S. President.”

Chavez in particular desperately requires the prestige such meetings can provide him; Venezuelan voters go to the polls in state and local elections just a few days before his meeting with Castro, and the results may indicate that Chavez’s popularity has fallen. Plummeting oil prices mean Chavez has far less leverage to bully his people, his neighbors and the United States, and less money to pay his mounting domestic and foreign bills. However, Medvedev’s visit to Chavez will coincide with joint Russian exercises off the shore of Venezuela. Perhaps the military spectacle will be enough to reinvigorate Chavez’s diminishing personal “brand”, even briefly.

For Raul Castro, who has stood in his brother’s long shadow for decades, these widely publicized gatherings let him position himself as a serious, recognized, long term leader among the world’s – for lack of a better expression -- anti-American nations.

Such public relations considerations take on added importance in light of the current international economic crisis. Russia quite simply has less ready cash to spare in support of allies like Cuba and Venezuela, and evidence indicates that many existing arrangements between these countries aren’t going according to plan. For example, Cuban negotiations with Russian oil giant LUKOIL to modernize two of its oil refineries “never proceeded beyond the very initial stages. A source close to the intergovernmental commission explained that Cuba received more profitable propositions from companies in other countries -- mainly the U.S.”

Throughout both terms of the Bush administration, the three nations have positioned themselves as leaders of what they call a “pluri-polar”, or “post-American”, world. Yet the election of Barack Obama helped alter international perceptions about the United States virtually over night. The hoary old cartoonish image of America as the world’s self-appointed “cowboy cop” suddenly seems comical. Can even the most hostile America bashers easily conjure up a mental image of this particular president elect wearing a big Stetson hat and firing six-shooters?

Regardless, as Ray Walser, Senior Policy Analyst for Latin America at the Heritage Foundation, told FrontPage, all three nations – Venezuela, Cuba and Russia – are “fixated upon historic illusions.”

“Chavez's Bolivarian dream, Castro's vision of keeping the Communist flame alive, and the Putin/Medvedev view of a Great Russia will cause turmoil in the region,” Walser predicts, “and test the mettle of the Obama Administration.”

Walser’s advice to the new President would be to “continue to press for real democracy in Venezuela and for a democratic transition for Cuba,” while building what might be called counterbalancing alliances with other regional players such as Colombia, Chile and Brazil.

Pulitzer Prize winning Miami Herald columnist Andres Oppenheimer recently offered some advice of his own for the president elect, based upon what he’s learned over many decades of covering the local “beat.” He wrote:

“Obama will not want to squander his party's growing inroads into the Cuban-American community, and the state's non-Cuban Latinos, by coming across as too close to Chávez, or the Castro brothers.”

Oppenheimer predicts that Barack Obama will lift restrictions on travel to Cuba, as he promised during his campaign. “He may even shake hands with Chávez at the Summit of the Americas next April in Trinidad and Tobago. But that's as far as he's likely to go.”

It isn’t in the interest of these anti-American leaders to make concessions to the United States, adds Oppenheimer. “They need to keep their conflicts with the United States alive to maintain a climate of imminent danger that justifies their authoritarian rule. (...) Don't expect big changes on that front.”

Longtime observers may recall that the last time Chavez met with a man named Castro, the encounter was a strangely memorable one. Chavez has always idolized Raul’s brother Fidel, modeling himself on the Cuban revolutionary and dictator. When the two got together back in 2000 to sign a $1-billion oil import agreement, the clownish Chavez cajoled his hero into joining him for, of all things, an off-key duet on live national radio.

Whether or not Raul Castro can be goaded into singing a nationalistic ballad with Chavez later this month remains to be seen (and heard). What seems certain is that Caracas, Havana and the Kremlin will continue to make music together for the short term at least, and it won’t be very beautiful to American ears.