Venezuela and Iran’s ties grow as warnings are raised about Trump pulling an ‘October Surprise’ on Tehran

• Increasing pressure from the US on Iran and other actions in the Middle East have raised concerns that Trump could seek a confrontation before the presidential election.
• At the same time, Iran has been working more closely with Venezuela, another US foe, raising the specter of a showdown much closer to home.
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Iran and Venezuela are two of President Donald Trump’s most frequent foreign-policy targets, and increasing US pressure has only brought the two closer.

Their ties are again on display ahead of the presidential election, as US actions directed at Iran raise concerns Trump could seek a confrontation for political benefit.

Such a showdown is a long-time goal for some members of the administration, according to Trita Parsi, an expert on Iran at the Quincy Institute for Responsible Statecraft, a think tank that advocates restraint in foreign policy.

The US and Iran have come to blows but stopped short of war, due in part to Trump’s seeming reluctance to start a new conflict. “Now, with the election, depending on how they judge [Trump is] doing, I think you may end up having an opening,” Parsi said.

That opening may come with Iran’s tankers, one flotilla of which has already delivered millions of barrels of gasoline to Venezuela, where years of neglect and mismanagement have eroded oil production and refining capability.

Another flotilla is arriving; two tankers docked there this week, and a third entered Venezuelan waters on Saturday.

The US has already seized Iranian tankers carrying gasoline to Venezuela, and framing future action as enforcing international law could make it more palatable to Trump, especially if Iran retaliates, but it may all depend on how Trump sees his reelection chances, Parsi told Insider.

Iranian officials have in the past said there would be "trouble" it the US interferes with its tankers, but in Tehran, the appetite for escalation is likely "very, very low," Parsi said.

Iranian leaders "don't want to do anything that could help Trump get reelected," but if the US seizes tankers closer to Iran — "inviting retaliation," Parsi said — "then it's going to be extremely difficult for the Iranians not to do something."

'Many options are on the table'

Iran and Venezuela, both founders of OPEC, have longstanding ties, and while low oil prices would ordinarily put them in competition, domestic and international factors — like Venezuela's falling oil production and the US pressure campaigns against both — make the partnership more appealing.

"Both Iran and Venezuela are caught up in the changing landscape of relationships between Russia, China, and the United States," said Harold Trinkunas, a scholar of Venezuelan politics at Stanford University.

US warnings go beyond fuel shipments, which allow both countries to skirt US sanctions. As the US has tried to extend a UN arms embargo and impose "snapback" sanctions on Iran, failing to get international support for either, officials have accused Venezuela of aiding Iran's malign activity.

During a sanctions announcement on September 21, Pompeo said the US was imposing more sanctions on Venezuelan President Nicolas Maduro, accusing his government of working with Tehran "to flout the UN arms embargo."

Two days later, Sen. Marco Rubio, a Florida Republican and influential adviser to Trump, suggested the embargo's October 18 expiration could bring Iranian arms to the Western Hemisphere.

Such sales are "a possibility if ... the conventional weapons ban is lifted against Iran. Now you can see them beginning to share weaponry with the Venezuelan military," Rubio said at the Hudson Institute, a conservative think tank.

Criminal and rebel groups in Venezuela could get those weapons, Rubio said, calling it "a catastrophic outcome" if those groups got "advanced weaponry" they could use to target Colombia, a close US ally.

Colombia's president recently alleged that Maduro wanted to buy Iranian missiles. Colombia's president didn't offer evidence, but days later Maduro said it was "not a bad idea" and asked the defense minister to look into it. Maduro tapped Venezuela's gold reserves to pay for Iranian gas, and experts are skeptical he can muster funds for weapons.

Rubio said "many options are on the table," including "physical prevention," to stop such a delivery. "I think that includes intercepting vessels at sea," Rubio said. "That's a real possibility. The US has sanctions, and it has a right to enforce them."

US officials have said intervening to stop Iranian tankers from reaching Venezuela was an option, a threat given weight by the US military's increased presence in the Caribbean for counter-drug operations and freedom-of-navigation exercises near Venezuela's coast. (The military wasn't involved in seizures earlier this year.)

The National Security Council declined to comment on the tankers' recent arrival. A spokesperson for the State Department's Bureau of Western Hemisphere Affairs said the deliveries were "another reminder of how, through its incompetence and mismanagement, the Maduro regime has destroyed Venezuela's institutions, economy, and infrastructure" and called Iran a "pariah" that was "propping up a despot at the expense of the Venezuelan people."

Foreign policy, domestic audience

Despite the rhetoric, US military intervention is considered unlikely.

"There is no sense here that Washington is looking for an excuse to take military action," said Phil Gunson, senior analyst for the Andean region at the International Crisis Group.

But "hardliners lament the lack of it," Gunson said, adding that it was "natural" to see such claims before a presidential election in which a portion of the US electorate with outsize influence supports an aggressive policy toward Venezuela.

Those claims "are about domestic as much as foreign policy, and they don't appear to be linked to actual action," Gunson added.

Trinkunas said additional sanctions were more likely, though with diminishing returns. More sanctions on more countries gives them "more and more incentives to work with each other," Trinkunas said. "In a sense, the more the US uses its sanction power, it undermines the overall effectiveness of sanctions."

Iran's need for hard currency means arms sales are possible, but they would come with risks and "may not be the top choice," Parsi said. "It all depends on what other options they have."

When tensions rose in the past, so did fears Iran could use its networks in Latin America to attack US interests, but that has always been seen as unlikely. (Those networks are believed to focus on activities like money laundering.)

Iran has better options closer to its own turf, Trinkunas said, and while Tehran showed a surprising degree "of sophistication and capability" with recent attacks in the Persian Gulf, Parsi said it was hard to believe it could do that so far from home.

"If suddenly the Iranians showed an ability to strike that far away from them, it would take the US by surprise," Parsi said, "but it would also risk war."