WASHINGTON — The Supreme Court on Monday confronted a question that could reshape U.S.-Cuba relations by interpreting a decades-long property rights law for the first time in 30 years.

The case, Havana Docks Corporation v. Royal Caribbean Cruises, wrangled with how U.S. courts enforce Title III of the Helms-Burton Act, a Cold War-era statute that allows U.S. nationals to sue cruise companies accused of profiting from property seized by Cuba’s communist government in 1960. The Trump administration is now the first to put Title III into effect after previous U.S. presidents repeatedly suspended the 1996 law to avoid complicating its relationship with Cuba. 

In 1934, the Cuban government approved Havana Docks, a U.S. company, to operate piers and terminal facilities at the Port of Havana until 2004. However, when Fidel Castro became Cuba’s new communist leader in 1960, the U.S. and Cuba entered a trade war, and the Cuban government confiscated all U.S. property on the island, including Havana Docks’ piers. 

In 1996, Congress passed the Helms-Burton Act, but it wasn’t until it became fully operational in 2019 that Havana Docks filed its lawsuit against the Cuban government. The U.S. company claimed Cuba trafficked their property.

In the hour-long argument, the justices hinged on interpreting specific terms written within the law by asking attorneys to define “property” and “trafficking.”

“What exactly is the property here that has been confiscated?” Justice Clarence Thomas asked. 

Havana Docks’ attorney Richard D. Klingler said “property” should be interpreted as the rights to operate the docks, land and machinery granted in 1934 by the Cuban government, which is “the equivalent of a leasehold.” 

However, Justice Ketanji Brown Jackson pushed back, saying it’s “a little confusing” how the U.S. Circuit Court of Appeals got to redefine what it means to be “trafficking in confiscated property” in light of this statute.

Justice Elena Kagan expressed skepticism over Havana Docks’ ability to sue in the first place, since they didn’t own the docks. 

“Whatever the definition of ‘property’ is, I mean, you can’t sue for property that you’re unconnected to, right?” Kagan said. “You can’t say, ‘The Cuban government seized a piece of property across the street … I think I’ll go bring a lawsuit about it.’”

Kagan said Havana Docks could have sued at any time from 1934 until 2004, the time during which the Cuban government allowed the U.S. company to operate in the area. However, once the concession expired, Havana Docks no longer had a property interest, she said.

But Klingler said the concession with the Cuban government theoretically would have been time-limited had there been no confiscation by Cuba in 1960.  

Assistant to the Solicitor General Aimee Brown echoed Klingler’s response. She told the Court that the cruise lines paid roughly $130 million to the Cuban government to use the docks in 1934, and therefore participated in “exploitation of confiscated property” in 1960. 

But Justice Sonia Sotomayor said the company’s interpretation could expose businesses to endless lawsuits. 

“The most you would’ve been entitled to is reasonable compensation at the time,” Sotomayor said. “But what you’re seeking is totally different. It’s infinite compensation forever.”

Havana Docks is seeking an approximate total of $439 million in damages from four major cruise lines for using Havana port facilities after confiscation by the Cuban government, according to an amicus brief.

Justice Brett Kavanaugh asked why lawmakers would design a system that allows damages potentially exceeding the value of the confiscated property. 

Klingler said Congress deliberately imposed harsh penalties to deter companies from engaging with Cuba at all, calling the statute a “key part” of U.S. foreign policy pressure.

The back-and-forth intensified when Paul D. Clement, representing the foreign cruise lines, said the Court should make a narrower reading of the statute grounded in its text. 

Instead, Clement said Havana Docks is overestimating how extensive their property rights were. Liability requires a “one-to-one correspondence” between the confiscated property and what was actually trafficked, he said. Havana Docks, he argued, only had temporary ownership of the docks and is therefore not entitled to compensation.

“If you ignore the time limits on concessions or leaseholds, you end up sort of treating relatively small sticks in the bundle as if they’re the whole kit and caboodle,” Clement said.

During Clement’s argument, Justice Neil Gorsuch pressed him on what exactly had been confiscated when Cuba seized control of the Havana port.

Clement said the company’s “time-limited interests” were taken, not the docks themselves. The Cuban government already owned the physical facilities, he said, and the statute applies only to the specific legal rights Havana Docks once held. 

In their heated exchange, Gorsuch asked Clement to once again clarify whether the docks were confiscated by Cuba. 

“I can’t agree to that, with all due respect,” Clement replied. “Cuba owned the docks.”

The justices are expected to issue a decision by summer.