“We’re very opposed to the authoritarian nature of Cuba, but you know, it’s unfair to simply say everything is bad,” Sanders said. “You know? When Fidel Castro came into office, you know what he did? He had a massive literacy program. Is that a bad thing? Even though Fidel Castro did it?”

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Anderson Cooper responded by pointing to Castro’s imprisonment of political dissidents.

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“That’s right,” Sanders said. “And we condemn that. Unlike Donald Trump, let’s be clear, you want to — I do not think that Kim Jong Un is a good friend. I don’t trade love letters with a murdering dictator. Vladimir Putin: not a great friend of mine.”

The exchange highlighted an issue that is likely to get a more thorough airing now that Sanders finds himself atop the Democratic field: His repeated comments offer varying degrees of praise for socialist authoritarian regimes over the decades. He has often decried U.S. adventurism in Latin America, coming out against the successful and attempted U.S. efforts to pick and choose who leads those countries. But he’s often gone further than just saying the United States should stay out.

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Indeed, the comment he was asked to respond to came in the 1980s, when he was asked why the Cuban people didn’t join the Americans in trying to get rid of Castro.

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“He educated their kids, gave them health care — totally transformed the society,” Sanders said.

(Note: This claim itself is a contentious one. The Post’s Fact Checker Glenn Kessler noted in 2016 that Cuba had a head start on other Latin American countries on education when Castro took over, and others made more significant strides.)

The two responses epitomize the fine line Sanders is walking here and arguably steps over. It’s one thing to say why the United States shouldn’t interfere in other countries’ politics and to offer analysis about why the people there should have self-determination; it’s another to emphasize the good in what are otherwise brutal regimes.

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Yet Sanders has repeatedly sought to do so:

In 1985, he called Nicaraguan leader Daniel Ortega “ a very impressive guy ” and downplayed reports of abuses by the Sandinistas, calling the Reagan administration “trained and well-paid people who are professional manipulators of the media.” He added: “Most of the poor and the working people I talked to felt that the situation now was much better than before. Rich people, needless to say, who used to have a good life, are not terribly happy.” He conceded, though, that “the Sandinistas make their share of mistakes."

In 1989, he said of Cuba : “For better or for worse, the Cuban revolution is a very profound and very deep revolution. Much deeper than I had understood.” And: “Cuba has solved some very important problems. I did not see a hungry child. I did not see any homeless people. Cuba today not only has free health care but very high-quality health care.” At the time, he added that Cuba’s imprisoning of dissidents showed it wasn’t a “perfect society. There are political prisoners in Cuba."

In 1986, he said of Cuba : “I was very excited and impressed by the Cuban revolution.”

In 1987, he said while talking about Cuba that the Reagan administration “seeks to prop up governments of the rich while attempting to destroy genuine revolutionary movements .”

In 1985, he said Americans opposed communist and socialist leaders because they didn’t understand the problems of poverty in those countries. “The American people — many of us — are intellectually lazy,” Sanders said.

In 1988, while visiting the Soviet Union, he praised it for having lower housing and health-care costs than the United States, while acknowledging the quality wasn’t as good.

Last year, he said of China : “China is a country that is moving unfortunately in a more authoritarian way in a number of directions. But what we have to say about China in fairness to China and it’s leadership is if I’m not mistaken they have made more progress in addressing extreme poverty than any country in the history of civilization, so they’ve done a lot of things for their people.”

As these comments show, Sanders has regularly acknowledged the problems within these governments, but he’s often strained to emphasize the positives that come with their more socialist styles of government. That perhaps shouldn’t be surprising, given who he is, but it’s also about the balance he has struck. And the balance is considerably different than basically any modern American politician.

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A good counterexample is then-Secretary of State Colin Powell’s comments in 2001 about Cuba. While testifying before Congress, Rep. Jose E. Serrano (D-N.Y.) argued for a rethinking of U.S. policy toward Cuba and mentioned how many doctors its health-care system produced.

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Powell caused a stir by acknowledging Castro had “done good things for his people.” He told Serrano, “You touched upon some of them.”

Even in that answer, though, Powell quickly and more strongly emphasized the negatives:

But for most of those 42 years and the part of my career when I was in the military, he was fomenting revolution, he was fomenting insurgencies, he was trying to impose a system that was not a system of freedom, a system that would have been disastrous for many of the nations in the region. And we had to meet him, we had to respond to that. We did. He’s no longer the threat he was. But 12 years ago, he was a real threat trying to destabilize this region; trying to have countries overthrown in order to put them under totalitarian leadership. It’s the same guy he was in ’59, the same gentleman he was in 1988 and ’89. He’s the same gentlemen in the year 2002 except he no longer has a strong power supporting him, a strong power subsidizing him. But he hasn’t changed his views in any way.