The US government's move to legally seize Iranian gasoline allegedly en route to Venezuela has raised more questions than it answers.

Last Thursday, the US secured a legal ruling in the District of Columbia federal court allowing it to claim the 1.16m barrels of gasoline aboard four Greek-linked tankers in its latest attempt to and topple the ruling regimes of Venezuela and Iran.

But what comes next is anyone's guess, as the US has to actually enforce the judge's decision.

"In order to proceed against the cargoes, the government would have to seize them, but they are on their way to Venezuela and unless they can be interdicted in some friendly jurisdiction along the way, they are likely to be simply taken to Venezuela and offloaded," said Seward & Kissel partner Bruce Paulsen.

Beyond that, the US is left with much trickier options, such as interdicting the ships on the high seas or blockading Venezuela — rare steps that could come with a significant diplomatic cost.

AIS beacons off

According to Dryad Global senior analyst Sophia Bellas, two of the four ships — the 37,400-dwt Bella (built 2000), 47,400-dwt Bering (built 1998), 46,200-dwt Pandi (built 1996) and 37,300-dwt Luna (built 2000) — were last seen in the eastern Mediterranean Sea.

Bellas said the ships are difficult to trace, as their AIS trackers have been turned off since May.

"I would argue that until the vessels are in US waters, or in a port with significant ties to the US where a local authority would act on their behalf, then the legal action is symbolic," she said.

"There is a sense that the US has been very much on the back foot since Iran/Venezuela gasoline shipments began on a regular basis, and I still don't believe the US has formulated a watertight response."

The US has tried in the past to enforce legal claims against ships abroad, but has failed.

Last year, it attempted to seize the 300,000-dwt Adrian Darya 1 (renamed Grace 1, built 1997) after it was detained in Gibraltar, but was rebuffed by authorities there.

During Iran's first set of gasoline shipments to Venezuela in late May and early June, the Wall Street Journal reported the US leaned on Trinidad and Tobago to intervene, as the ships were set to pass through its territorial waters.

Instead, the island country requested that the tankers avoid its jurisdiction.

Success against ships

The US has been more successful by threatening sanctions against ships and their owners. The flotilla carrying the first delivery of gasoline included two Greek-owned tankers that reversed course once threatened with a blacklisting.

The remaining five, all Iranian-flagged, completed the journey.

The US then threatened as many as 50 ships with addition to its sanctions, adding six Greek-connected ships and their registered owners in an opening salvo.

All were removed by last Thursday, as many owners publicly pledged to stay out of Venezuela while President Nicolas Maduro remains in power.

This latest shipment uses Liberian-flagged ships, connected to either Vienna Ltd or Palermo SA, both based in Piraeus.

These two companies, TradeWinds has reported, are connected to IMS principal Captain George Gialozoglou.

Neither IMS nor Palermo responded to requests for comment by TradeWinds and contact information could not be found for Vienna.

Iran connection

In court, the US argued the shipments were arranged by an Iranian businessman, Mahmoud Madanipour.

Madanipour is said to have connections to the Iranian Revolutionary Guard Corps (IRGC), the country's military, and according to the US, a terrorist organisation.

He allegedly has a long history using the sorts of deceptive shipping practices the US has sought to crack down on to evade sanctions, including ship-to-ship transfers and routing payments through other countries to avoid suspicion.

The US has argued Iran's oil industry supports the IRGC, and thus terrorist acts aboard.

Iran and Venezuela respond

At a military parade celebrating Venezuela's independence day on Sunday, Maduro reportedly called US sanctions "criminal" and said that he expected the country to back off as Venezuela fights Covid-19.

"On the contrary, they intensified their criminal sanctions, a campaign against food, against medicine, against petrol that Venezuela seeks and buys in the world," he said according to Iranian English-language news outlet Press TV.

Venezuela has 7,169 cases of Covid-19 and 65 deaths related to the respiratory illness, data from Johns Hopkins University shows.

According to Russian state-linked news site Sputnik, Iran's First Vice President Eshaq Jahangiri said on Sunday that the US has failed to prevent Iranian oil exports.

"Under the previous sanctions, the maximum amount of oil exports for Iran was set at 1m barrels and then we were selling up to 900,000 barrels of oil. Now they [Washington] said that Iran’s oil exports should be brought to zero, and, fortunately, they failed to achieve this," Jahangiri said.