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Tanker Shenlong Suezmax carried oil from Saudi Arabia through the Strait of Hormuz earlier this month. The tanker is managed by Dynacom Tankers, according to Reuters, one of the few companies willing to send vessels through the waterway since the war began.Rafiq Maqbool/The Associated Press

When U.S. President Donald Trump called on the owners of oil tankers to “show some guts” and sail through the Strait of Hormuz, he might have been thinking about George Prokopiou.

The billionaire Greek shipping tycoon has been one of the few willing to risk the dangerous waterway within striking distance of Iranian missiles and drones. His company, Dynacom Tankers Management Ltd., has seven tankers that have either gone through the strait or have set sail to do so since Iran’s war with the U.S. and Israel began.

“The Greek owners and operators have typically a higher risk appetite, a higher risk tolerance,” said Bridget Diakun, an analyst with Lloyd’s List Intelligence, which provides maritime risk analysis.

Mr. Prokopiou, 79, certainly has a reputation for pushing the envelope. “If you are not a risk-taker, you are not in shipping,” he told the shipping publication Tradewinds in 2014.

He bought his first ship in 1971, a tanker named Pennsylvania, and built one of the largest shipping conglomerates in the world, consisting of more than 100 vessels. Dynacom alone owns 73 tankers, including dozens of very large crude carriers, or VLCCs, which can transport as much as two million barrels of oil, and has orders for 50 more.

He’s also branched out into real estate, with more than 2,000 properties around the world, ranging from a stake in the Astir Palace Hotel in Athens to the city’s historic Skaramangas Shipyards.

Rarely seen without a baseball cap, Mr. Prokopiou spends most of his spare time on his US$150-million superyacht called Dream, which is docked on the Athenian Riviera.

He courted controversy after Russia’s full-scale invasion of Ukraine in 2022 by continuing to carry Russian oil. “Sanctions have never worked,” he told a shipping conference in August, 2022.

Ukraine’s National Agency on Corruption Prevention put Dynacom on its list of “international sponsors of war” in 2022 but removed the company a year later after negotiations. The list itself was pulled from public view in 2024.

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Since the the war in Iran started three weeks ago, Mr. Prokopiou has not hesitated to seek a profit.

While the costs of moving oil through the strait have skyrocketed – notably for insurance and extra pay for crew members willing to make the trips – the profit can be substantial. Companies such as Dynacom have been charging about US$400,000 per day to use their tankers, roughly four times the price before the war. Some of the vessels are for shipping while others are for storing oil at sea as land-based facilities around the Gulf reach capacity.

The Iranian military has managed to effectively close the narrow Strait of Hormuz, a critical passageway for roughly 20 per cent of the world’s oil supply.

So far, 16 vessels have been attacked and six others have reported incidents affecting their operations, according to the United Kingdom Maritime Trade Operations Centre. More than 700 ships remain trapped in the Persian Gulf.

Some ships have been getting through. According to Lloyd’s List, some 100 vessels have made the voyage since March 1, including bulk carriers, container ships and oil tankers. That’s down from nearly 1,900 during the same period last year, but it’s clear that at least a few owners are prepared to take their chances.

Roughly one-quarter of the ships had a connection to Iran, 18 per cent had ties to Greek owners, and 10 per cent had links to China. Two ships connected to each of India and Pakistan also made the journey last week with Iran’s explicit blessing.

Dynacom has been by far the biggest player among the Greek operators. Of the seven ships it has in the Persian Gulf, two have gone through the strait and five are fully loaded and on their way, ostensibly carrying oil from Saudi Arabia to India.

The company’s success is being watched closely.

“I imagine if Dynacom is able to get all of its vessels out safely, that it will encourage others to try to do the same,” Ms. Diakun said this week during a briefing organized by the London-based International Institute for Strategic Studies.

She added that “each and every single owner and operator is going to make their own decisions based on their risk profile and their risk appetite. And it’s a very, very wide range.”

For its part, Iran has insisted that the strait remains open – to all ships save for U.S. and Israeli vessels.

Most of the ships navigating the strait keep their automatic identification systems, or AIS, turned on and sail close to the coast of Iran. That’s likely to alert the Iranians, who have been checking carefully.

“Broadly speaking, it’s anything that doesn’t have a U.S. nexus or an Israeli nexus,” Ms. Diakun said of the ships allowed through.

The Iranians “are going to be casting a really wide net when they’re looking for this. We understand they’re asking a lot of details on historical ownership, ports of call, all of that.”

It’s likely Dynacom has made some arrangements with Iran to transit the strait. “I would say there’s not a ton of evidence to suggest that anyone has a free pass through the Strait of Hormuz,” she said.

The Globe and Mail reached out to Dynacom for comment but received no reply.

Mr. Prokopiou’s risk appetite isn’t welcomed by everyone.

“Iran has explicitly warned that ships will be targeted, so why would any company risk the lives of civilian crews?” said Stephen Cotton, general secretary of the International Transport Workers’ Federation, which represents thousands of seafarers. “Executives who knowingly send crews into a clearly declared war zone must expect to be held accountable for the consequences.”

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