Donald Trump’s administration regularly denounces Nicolas Maduro as an autocratic Cuban puppet and may hit the Caribbean island with new sanctions over its support for the Venezuelan leader.

The U.S. president is expected to decide soon whether to activate a controversial section of American law toward Cuba for the first time ever, with other measures meant to tighten the screws on Havana likely to follow. The first move, known as Title III, would allow Cuban Americans to sue companies “trafficking” in property confiscated during the 1959 revolution in U.S. courts.

That would complicate Cuba’s attempts to bolster its economy by attracting foreign investors. The measure is one of the remaining pieces of leverage the U.S. has in its effort to pressure countries into paring support for Maduro’s regime, which has long depended on Cuban political and logistical backing that to some observers has more symbolic power than substantive impact.

“There’s not going to be any resolution in Venezuela without somehow neutralizing the role of Cuba,” said Jose Cardenas, who held senior Latin America posts in George W. Bush’s administration. “Cuba is seen as the bulwark behind Maduro’s intransigence -- they are steeling his spine.”

Cracking down on Cuba is risky for Trump. Unless he applies sanctions surgically, they could become headaches for nations like Canada and the European Union, similar to his decision to withdraw from the Iran nuclear accord last year. A further isolation of Cuba could also drive a wedge into the regional bloc backing efforts to recognize Venezuela’s opposition leader Juan Guaido as its legitimate president.

In the Crosshairs

Along with Canadian miner Sherritt International Corp., European airlines such as Air France-KLM and Deutsche Lufthansa AG, along with Spanish firms NH Hotel Group SA and Melia Hotels International SA, Dutch-British consumer goods conglomerate Unilever NV and Swiss food giant Nestle SA appear on lists of potential Title III targets tabulated by Cuba watchers.

The U.S. law is part of the Helms-Burton act, passed under the Clinton administration in the 1990s. Title III had been waived on a rolling six-month basis until last month, when the State Department broke the status quo with a 45-day suspension. It said it was assessing how best to respond to Cuba’s “brutal oppression of human rights” and “indefensible support” for authoritarian regimes in Venezuela and Nicaragua -- the third member of what National Security Adviser John Bolton labels the “Troika of Tyranny.”

While it is gospel among anti-Maduro forces that Cuba is pulling the strings, it’s difficult to prove conclusively. Two days after Trump, in a Miami speech that railed against socialism, condemned the “corrupt bargain” of Venezuelan oil for a “police state run directly from Havana,” Cuba’s foreign minister called a rare press conference to deny the accusation as “calumny.”

A former Canadian ambassador to Venezuela acknowledged Cuba’s presence in the oil-producing South American nation is significant but misunderstood.

“It’s not that one country is dominating the other, it’s that the two have established a strategic partnership,” Ben Rowswell, who served in Caracas from 2014 to 2017, said after briefing lawmakers in Ottawa last week. “They each believe the other is essential to their own narrative about why they are legitimate.”

Extraterritorial Implications

With the 45-day deadline looming -- and a 15-day notification period for Congress -- a decision on Helms-Burton could come by the end of this week. For another former Canadian diplomat, that’s resulted in a case of deja vu.

“The implementation of Title III would be, as it was in 1996, an egregious extraterritorial extension of U.S. law,” said Mark Entwistle, who was ambassador in Havana when it was debated and passed. “It would directly impinge on the sovereign right of other countries to conduct their own foreign policy.”

The Canadian government is awaiting clarity from the U.S. on its intentions for Title III, according to Foreign Minister Chrystia Freeland’s office. “We will always stand up for Canadian businesses,” press secretary Adam Austen said.

Canada, which hosted a meeting of the Lima Group of nations backing Guaido’s claim to Venezuela’s presidency earlier this month, never broke relations with Cuba after Fidel Castro seized power. The northern nation sends a million tourists to the Caribbean island each year and is home to its largest private investor.

Potential Exemptions

Sherritt has been mining nickel in eastern Cuba since 1994 and also has oil-and-gas operations near Havana. The Toronto-based firm has already been penalized under Title IV of Helms-Burton, with executives banned from traveling to the U.S. as a result. It declined to comment on the potential implementation of Title III.

U.S. companies that bolstered ties to Cuba after an easing of restrictions under former President Barack Obama could also be targeted, including United Continental Holdings Inc., Marriott International Inc. and Carnival Corp. But Cardenas expects Trump to exempt both American firms and those of allied nations from any application of Title III.

“I would find a way to exempt countries that have been playing a positive role in Venezuela,” the former Bush official said, laying out four other ways the Trump administration could ratchet up pressure on Havana:

  • The Treasury Department could review all business licenses issued under Obama. That could jeopardize a recent Major League Baseball deal as well as continued visits by American cruise ships to Cuba.
  • The U.S. could target individual Cuban officials active in Venezuela with Magnitsky sanctions. Cardenas said retired Venezuelan military officers living in the U.S. are helping to compile a list of such individuals.
  • Trump could restore a fast-track immigration program for Cuban doctors who defect to the U.S. that was eliminated under Obama’s normalization.
  • The U.S. could return Cuba to its list of state sponsors of terrorism. Cardenas cited the presence in Havana of Colombian guerrillas behind a Bogota bombing as well as Cuba’s role in forming paramilitary groups Maduro uses to crush dissent as grounds.

Given the delicate regional politics at play, Canada’s former envoy to Havana is leery of any possible U.S. crackdown.

“I’m hoping Cuba is not thrown like the proverbial baby in the bathwater in with the Venezuelan crisis,” said Entwistle, who now advises U.S. multinationals doing business on the island. “I think it would be a strategic error.”