Not for the first time Cuban forces are doing Russia’s dirty work, this time in Syria. On Wednesday it was reported that a U.S. official had confirmed to Fox News that Cuban paramilitary and Special Forces units were on the ground in Syria. Reportedly transported to the region in Russian planes, the Cubans are rumoured to be experts at operating Russian tanks.

For President Obama, who has staked his legacy on rapprochement with America’s adversaries, the entrance of Cuba into the bloody Syrian civil is one more embarrassment. Russia, Iran, and Cuba—three regimes Obama has sought to bring in from the cold—are now helping to prop up the regime of Bashar al-Assad, ruler of a fourth regime he also tried in vain to court early on in his presidency. Obama has been holding his hand out in a gesture of goodwill to America’s adversaries only for them to blow him a raspberry back in his face—while standing atop a pile of Syrian corpses.

Yet for seasoned Cuba-watchers the entrance of the Cuban Revolutionary Armed Forces into the Syrian civil war is a surprise but hardly a shock. A surprise because Cuba was forced two decades ago to curtail its military adventurism by a deteriorating economy (the Cuban military has been reduced by 80 percent since 1991).

Largely thanks to the involvement of Cuban troops in the fight against Apartheid South African in Angola in the ’70s and ’80s (not to mention the more recent medical “missions” to disaster-stricken parts of the world) Cuba has gained something of a reputation for internationalism. At one point the Cuban presence in Angola reached 55,000 soldiers, inflicting a defeat on South African forces which helped precipitate the end of apartheid. “The [Cuban army’s] decisive defeat of the aggressive apartheid forces [in Angola] destroyed the myth of the invincibility of the white oppressor,” Mandela told the Cuban leader on a visit to Havana in 1991.

In recent years Angola has lent the Castro regime a romantic penumbra which says that, for all its faults, the Cuban revolution is on balance progressive (watch the film Comandante by the ludicrous Oliver Stone to get a sense of what I mean).

Yet while everyone remembers Cuban heroics in Angola, few remember Cuban terror in Ethiopia.

Those of us who are old enough probably recall the Live Aid concert organised by Bob Geldof in 1985, put on to raise money to help alleviate Ethiopia’s worst famine in a century. 400,000 people died in the famine of 1984/85, and while many people remember the gut-wrenching television images of fly-speckled children with pronounced rib cages and distended stomachs, few know that the tragedy was largely a consequence of the policies pursued by the Communist dictatorship that ruled Ethiopia at the time—a regime propped up by Cuba and the Soviet Union.

The Russians airlifted 17,000 Cuban troops to Ethiopia over the 14 years the Dergue—the dictatorship which ruled Ethiopia—were in power. During 1977-78 it is estimated that over 30,000 Ethiopians perished as a result of the Red Terror unleashed by the Communist government. During the terror, Sweden’s Save the Children Fund denounced the execution of 1,000 children—children whom the communist regime had preposterously labelled “liaison agents of the counter revolutionaries”.

As with Stalin’s war on the kulaks in the ’30s, Ethiopia’s Marxist government embarked on its own utopian ventures in the countryside, forcing between 12 and 15 million Ethiopians into collectivized farms. According to Alexander De Waal, one of the foremost experts on the Horn of Africa, “more than half this mortality [400,000] can be attributed to human rights abuses that caused the famine to come earlier, strike harder, and extend further than would otherwise have been the case.” The Ethiopian army, reinforced by Cuban troops, prevented the distribution of food to areas of the country whose inhabitants were rumoured to be sympathetic to opposition groups.

Following Russia’s lead, Cuba’s alliance with African nationalism extended to support for the bloody regimes of Nguema Macias in Equatorial Guinea and Idi Amin in Uganda. Cuba also gave political cover to the Soviet invasion of Afghanistan—an odd position for a member of the non-aligned group of nations to take, until you consider that the Soviet Union might have limited the massive aid it sent to the island had Cuba stepped out of line.

A genuine affinity certainly exists between many of the world’s dictatorships based on a common hatred of the liberal democracies. Quickly sensing the way the wind was blowing in Tehran, the former Cuban President Fidel Castro was one of the first heads of state to recognize the Islamic Republic of Iran in 1979, informing then-Supreme Leader Ayatollah Khomeini (disingenuously for someone who had previously interned religious believers in labor camps) that there was “no contradiction between revolution and religion.” Similarly cordial relations have also long existed between Cuba and Syria, where Cuba has intervened militarily in the past. From 1973 to 1975 a Cuban tank brigade was stationed facing the Golan Heights after the Israeli victory in the Yom Kippur War. In 1985, then-Syrian President Hafez al-Assad wrote to Fidel Castro honouring the friendship between both countries as beneficial “for the two peoples in their joint struggle against world imperialism and its allies.

Ultimately, though, Cuba’s reported entrance into the conflict in Syria should be seen as the island paying new dues to its benefactor in the Kremlin. While the Obama-Castro relationship has filled the headlines in recent months, the overtures the Russian leader Vladimir Putin has been making toward Cuba have gone largely unnoticed. Last year Putin wrote off a massive $32 billion of Cuba’s debts to Russia—a 90 percent reduction in what was previously owed. Putin also pledged to assist oil exploration projects off Cuba’s northern coast and reopened Russia’s Cold War spy base in Lourdes, south of Havana.

Putin is reportedly indignant at the U.S. for what the Russian president considers to be U.S. meddling in his country’s “backyard” in Ukraine. Putin’s generosity toward Cuba is thus an attempt to wrestle back the initiative by discomfiting the United States 90 miles off the coast of Florida. But Russia’s newfound enthusiasm for Cuba has another happy side effect: just like in old times a Russian leader can ask its Cuban padawan to get its hands dirty.

UPDATE 10/28/15: The Cuban government and White House Press Secretary Joshua Earnest have both denied Fox News’s report that Cuba sent troops to Syria to help prop up the Assad regime.