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In 2014, that bet began to pay off. The Obama administration announced an end to Americas decades-long enmity with the Cuban government, and soon everyone from Conan OBrien to Andrew Cuomo to Steve Nash began showing up in Havana. As a University of Miami Cuba expert, Michael J. Bustamante, noted at the time, the American flag has even become the most stylish national standard, appearing on Cubans T-shirts, tights and tank tops.

Then Mr. Trump entered the White House and it all fell apart. In 2019, he imposed the harshest economic sanctions in more than a half-century. A month later, Cuba began rationing soap, eggs, rice and beans. Around that same time, according to The Wall Street Journal, Chinas surveillance network on the island underwent a significant upgrade (the Cuban and Chinese foreign ministries have denied reports of a Chinese surveillance facility in Cuba). Evan Ellis, a Latin America analyst at the U.S. Army War College, told The Journal that the deal is basically Chinese pay-to-play, adding that China gives money to Cuba it desperately needs, and China gets access to the listening facility. Last fall, China agreed to restructure Cubas debt and donate $100 million to the island. One reason Cuba still needs Beijings money is that the Biden administration has kept key Trump sanctions in place.

U.S.-Iran relations follow a similar pattern. When the two countries signed the 2015 nuclear deal, Irans foreign minister at the time, Mohammad Javad Zarif, called it not a ceiling but a solid foundation. We must now begin to build on it. Irans leaders, like Cubas, hoped better relations with the United States would spur Western investment. Although some Iranian hard-liners feared that economic ties to the West would weaken the regime, Mr. Zarif and President Hassan Rouhani gambled that a stronger economy would strengthen Irans regional position and defuse popular discontent, thus helping solidify the countrys despotic political system.

It didnt work out that way. Mr. Trump canceled the nuclear deal and reimposed harsh sanctions. Rather than re-enter the agreement on its first day in office, the Biden administration made additional demands, which helped thwart efforts to revive the deal. And as the prospect of substantial U.S. and European investment disappeared, so did Washingtons leverage over Irans relationship with Moscow. Iran now has little to lose by developing what a National Security Council spokesman recently called a full-scale defense partnership with Russia.

This isnt the first time the United States has driven smaller nations into the arms of its superpower adversaries. It did so during the Cold War. In his book Embers of War, Fredrik Logevall notes that until the late 1940s, Ho Chi Minh, the Vietnamese nationalist leader, believed the United States could be the champion of his cause of independence from France. During World War II, Mr. Hos rebel army, the Viet Minh, worked alongside the Office of Strategic Services, the precursor of the C.I.A., in Americas fight against Japan.

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Opinion | Why Iran and Cuba Turned Their Back on the U.S. - The New York Times