A Russian air force Ilyushin Il-62M jet that arrived with troops and equipment in Venezuela over the weekend is seen at Simón Bolívar International Airport outside Caracas on March 28. (Yuri Cortez/AFP/Getty Images)

After two Russian military planes landed near Caracas this month, the Trump administration issued stark warnings over President Nicolás Maduro’s ties to the Kremlin. But a vessel that arrived in the waters off Venezuela’s Caribbean coast a day earlier offered a more telling sign of a deepening relationship that is so alarming to Washington. 

Venezuela has the world’s largest known oil reserves, with transport and sales of its thick, sludgy crude long dependent on chemical thinners purchased from the United States. After Washington barred U.S. companies from selling them to Venezuela in January — and warned foreign companies to follow suit — Maduro faced a dire predicament: How would he stave off the industry’s total collapse? 

Like manna from Moscow,
an answer arrived in the form of a red-and-black tanker, the Serengeti, that loaded a cargo of thinners off the coast of Malta before arriving in Venezuela on March 22. The company that chartered the vessel: Russia’s state-run oil giant Rosneft. 

SAN ANTONIO, VENEZUELA - FEBRUARY 19 A girl (MOTHER DID NOT WANT HER IDENTIFIED) follows her mother towards the border with Colombia in the border town of San Antonio, Venezuela on February 19, 2019. Many Venezuelans cross the border to buy goods for cheap or that are unavailable in their own country due to the ongoing economic and political crisis. Others simply cross the border with their possessions to start a life in a new country. (Photo by Michael Robinson Chavez/The Washington Post)

“Relations between Russia and Venezuela are excellent,” Alexey Seredin, minister counselor at the Russian Embassy in Caracas, said in an interview. “At the moment, we are working to strengthen cooperation.” 

The arrival of vital diluents is only one part of an expanding Russian footprint in Venezuela. Moscow is dispatching military personnel and equipment and is acting to offset U.S. sanctions by shipping Venezuelan crude to India for processing. The Kremlin is poised to increase wheat sales and dispatch more medical aid. This month, Venezuela also announced the opening in Moscow of a regional headquarters for PDVSA, its state-run oil giant. 

Next week, Seredin said, a senior delegation from Maduro’s government will arrive in Moscow to discuss Russian investments in Venezuela’s mining, agricultural and transport sectors. Seredin added that the arrival of 99 Russian military personnel on March 23 was part of an effort to maintain Maduro’s defense apparatus, which includes Sukhoi fighter jets and antiaircraft systems purchased from Russia. 

In a televised event Friday, Venezuelan Defense Minister Vladimir Padrino López inaugurated an “Armed Force Center of Flight Simulations” for Russian helicopters.

“This center, and we say it humbly, can only be found in Venezuela and Russia,” he said.

He also announced plans for a Russian Sukhoi MK2 simulator in the Venezuelan city of Barcelona, and insisted that a long-delayed plant to produce Russian rifles would open soon” in Maracay.

In an era of generally warming ties between the Trump administration and Moscow, Russia’s deepening involvement in Venezuela is creating a flash point by challenging the U.S. effort to force Maduro from office. 

President Trump said Friday that he is likely to speak with Russian President Vladimir Putin and Chinese President Xi Jinping about the crisis in Venezuela. Earlier in the day, national security adviser John Bolton was more pointed, issuing a statement that condemned the “introduction of Russian military personnel and equipment into Venezuela” as a “provocative” act and a “direct threat to international peace and security in the region.”

Elliott Abrams, the special envoy for Venezuela, declined Friday to elaborate on Bolton’s suggestion of military intervention.

“There are a lot of things we can do in economic terms, in terms of sanctions,” Abrams told reporters in Washington. “We have options, and it would be a mistake for the Russians to think they have a free hand. They don’t.”

With more than 50 nations recognizing National Assembly leader Juan Guaidó as Venezuela’s rightful leader, Maduro is managing the country’s new status as a pariah state by largely operating outside the Western systems of trade and finance, while turning to Russia, and to a lesser extent China and India. 

Russia’s backing of Maduro in the face of the U.S. effort to depose him is increasingly being compared to the Kremlin’s intervention in Syria on behalf of President Bashar al-Assad. In 2015, Russian involvement turned the tide in Syria’s civil war, preserving Assad’s power and elevating Moscow into a seeming kingmaker in the Middle East. 

“There is an understanding that [Venezuela] is a rather serious test for Russia’s ability to act in defense of its interests globally,” said Dmitri Trenin, head of the independent Carnegie Moscow Center think tank. 

It is unclear whether Russian intervention will be enough to counter the nationwide blackouts and gasoline shortages aggravating the humanitarian crisis that has left millions without access to enough food and medicine. Russia’s pockets, many argue, are not deep enough to keep Maduro in power. 

Yet, coupled with Chinese support, Russia’s efforts have appeared at least to ease some of the immediate pressures. The arrival of Russian military personnel this month appeared to signal Moscow’s willingness to ramp up its backing of Maduro, as well as ready his war machine at a time when the Trump administration has not ruled out a military intervention. 

“It’s an ideological chess game. Russia does not need Venezuelan oil,” said Russ Dallen, a Florida-based managing partner at the brokerage Caracas Capital Markets. “Venezuela is far from their supply lines. It was more an opportunity to stick their finger on Uncle Sam’s eye in the U.S.’s backyard.” 

China — another Maduro benefactor — has offered more-subdued support. Last week, Beijing barred Guaidó’s representative from a scheduled meeting in China of the Inter-American Development Bank, prompting the multilateral lender to cancel the event. Last month, China joined Russia to veto a U.N. Security Council resolution, drafted by the United States, calling for a new presidential election in Venezuela. 

Yet Chinese officials — eager to defend their investment in Venezuela — have for years played both sides of the fence by holding regular meetings with Maduro’s opposition. In February, Chinese diplomats held talks with senior opposition officials in Washington, according to two people familiar with the meetings. The opposition’s pitch: Your investments will be safe if Maduro falls. 

On Friday, Maduro’s government announced a Chinese gift of 65 tons of medical supplies. The announcement came on the same day that the Red Cross said it would begin distribution next month of large-scale aid for 650,000 Venezuelans facing the worst conditions.

“This aerial bridge that we are building with China represents an important investment in our people,” Maduro’s industries minister, Tareck El Aissami, told reporters in Caracas. 

Russian cooperation with Venezuela dates to arms deals struck with Hugo Chávez — Maduro’s predecessor and socialist mentor. Between 2006 and Chávez’s death in 2013, Venezuela bought nearly $4 billion in Russian military equipment, including an estimated 5,000 MANPADS surface-to-air missiles. 

Military cooperation led to massive Russian investments in Venezuela’s oil sector, and a willingness to extend loans on favorable terms. In early December, two nuclear-capable, long-range Russian Tu-160 bombers arrived at the international airport outside Caracas. The Russian aircraft later took part in joint exercises. 

But Russia has far less potential firepower to theoretically deploy in Venezuela than it brought to bear in Syria — in part because Venezuela is so far away. Russia has no full-fledged military base in the region, and its only aircraft carrier is out of commission. 

“There will be political, moral support,” said Fyodor Lukyanov, a Russian foreign policy analyst who has advised the Kremlin. “But Russia can’t send an armed contingent over there. It’s just not realistic.” 

Yet economic lifelines may be more important for Maduro’s survival. The U.S. sanctions issued in January blocked Venezuela from selling its crude to the U.S. refineries designed to process its high-viscosity crude. This month, shipping in and out of Venezuela has been chaotic amid nationwide power blackouts. But at least one tanker left Venezuela for India, carrying Venezuelan crude to a partly Russian-owned refinery, said Dallen, the Florida-based broker. 

Before the U.S. sanctions, Venezuela exported crude to the United States and imported the gasoline refined from it. The sanctions left Maduro struggling to address a sudden shortage of gas. Ivan Freitas, a PDVSA union leader, said that reports from port workers with access to vessel schedules show that Rosneft delivered at least one shipment of 300,000 barrels of gasoline to Venezuela last month, with roughly 1.6 million more barrels expected to arrive but not yet confirmed. 

“Rosneft has become the savior of PDVSA,” Freitas said. “The company’s help is buying time . . . for Maduro.”

Rosneft did not respond to a request for comment.

Russian assistance extends beyond the oil industry. Last month, Moscow delivered 7.5 tons of medical supplies and pledged to ship 7.7 tons more. Though of minimal help in light of the massive problems confronting understaffed, undersupplied and deteriorating hospitals across Venezuela, the Russian aid provided Maduro with a public relations coup.

Inside the Ana Francisca Pérez de León Hospital in eastern Caracas on Friday, its pro-Maduro director, Zayra Medina, said the Russian aid arrived Feb. 23, escorted by a Russian man, an interpreter and a man with a video camera. She said the hospital went through the supplies in about 10 days.

“We hope they keep helping us,” she said. “I feel happy knowing we’re not alone. Russia is helping us save lives in the middle of a storm.”

Faiola reported from Miami and Troianovski from Moscow. Anna Fifield in Beijing and Carol Morello in Washington contributed to this report.