Now Starts The Hard Part Of Pulling The U.S. And Cuba Out Of Their Cold-War Time Warp

Jan 21, 2015

A car in Havana sports Cuban and U.S. flags in advance of talks there to normalize relations between the two countries.
Credit Day Donaldson / Flickr/Creative Commons

Like Michael J. Fox struggling to power his DeLorean back to the future, the United States and Cuba on Wednesday start the labor of propelling their relations out of a Cold-War time warp and into the 21st Century.

Senior officials from both sides will meet in Havana to make history. They’ll launch talks to re-establish diplomatic ties that were severed 54 years ago in the wake of Cuba’s communist revolution.

It won’t be easy. The mutual distrust still runs deep and bitter. So I spoke with two veteran U.S. diplomats who know first-hand what it’s like to sit across the table from the highest level of Cuban officialdom, including the Castros themselves.

RELATED: Why It's Time For A Reality Check On Normalizing Relations With Cuba

Let’s cut to the chase. Here’s what they say Assistant Secretary of State Roberta Jacobson, who leads the U.S. delegation, can expect:

“Well, it’s going to be very frustrating for her,” says Coral Gables Mayor James Cason, who was America’s de facto ambassador to Cuba from 2002 to 2005 as head of the U.S. Interests Section there. (That’s like an embassy when countries don’t have formal ties.) “It’s going to be a long process.”

“The Cubans are going to move slowly,” says retired U.S. Ambassador Vicki Huddleston, who ran the Interests Section in Havana from 1999 to 2002. “They’re very afraid of risk.”

Both say the first test will be whether the Cubans try to keep the old restrictions on the new relationship.

“We’re gonna find out whether the Cubans really want to normalize relations in the sense of allowing our diplomats to act normally as we would in any other country,” says Cason.

It's going to be very frustrating for the U.S. delegation. It's going to be a long process. -James Cason

That means things like letting U.S. diplomats travel freely around Cuba – right now they can’t leave Havana without special permission – and Cuban officials not inspecting U.S. diplomatic mail.

The Cuban diplos – who can’t leave Washington, D.C., without U.S. authorization – have their own demands, like being taken off the U.S. list of countries that aid terrorism.

That is likely to happen. But at the same time, says Cason, the Cubans “will not want to discuss anything to do with human rights. They will say, ‘We don’t have any human rights problems, you’ve got Ferguson, you should pay attention to your problems.’”

Cason doesn’t agree with normalizing relations. During his time in Cuba he was best known for irking the government with pro-democracy efforts like helping dissidents set up independent libraries. (That was before the rules about not leaving Havana were set in stone.)

“I was able to travel the first three months over 7,000 miles around the island and visit all the homes of the dissidents,” he says.

In retaliation, he recalls, the Cuban regime produced animated, anti-U.S. cartoons that depicted him “as a rat. I would turn into a rat and I would be beaten up by the crowd and I would scurry into the Interests Section. These are videos they continue to show, between innings [of] baseball games.”

Cason argues episodes like that are indicative of how ideologically entrenched Cuba’s communist officials can be. (Although Cuban officials often complained to me that Cason, a conservative Republican, was as dogmatically hard-headed as any of them were.)

Where we accomplished things was dinner at my house after formal talks...with a glass of wine. -Vicki Huddleston

But Huddleston, who supports normalization, says her experience as the top yanqui diplo in Cuba was somewhat different -- once you got away from the negotiating table. She points to the 2000 Elián González crisis as a prime example.

“We didn’t accomplish much at the [formal] talks,” she says. “But where we accomplished things [was] at dinner at my house afterward in the evening – once on my birthday, actually. And then we could talk, informally, with the Cubans, with a glass of wine.

And so, where [Jacobson and the U.S. delegation] will make progress, it seems to me, is [in] informal, behind-the-scenes talks.”

That was also apparent, Huddleston adds, after 9/11, when the U.S. wanted to use its military base at Guantánamo on Cuba’s eastern tip to imprison terrorism suspects.

The Cubans weren’t thrilled about it, but behind closed doors, “I said, ‘It seems to be it would be prudent if you acquiesced in this, because if you don’t it will seem as if you are indirectly supporting the terrorists,’” says Huddleston. “And in fact they cooperated with us.”

It turns out the Cubans were right about how controversial Guantánamo would become. Either way, U.S. officials say Jacobson has already formed a working relationship with her Cuban counterpart, Josefina Vidal, and Huddleston says that will be the biggest asset this week.

DOGGED DIPLOMACY

Perhaps most important, like Cason with the rat cartoons, Jacobson will have to keep her sense of humor. Huddleston had her own run-ins with Fidel Castro – one involving not a rat but a dog.

“A Cuban Afghan hound,” she recalls. The breed is popular in Cuba and has a kennel club. But when Huddleston got one of her own there, the club said her dog couldn’t join “because of my country’s policies and my own actions.”

So Huddleston went on a public humor campaign, declaring that U.S. diplomats in Cuba were “on a short leash… in the dog house.”

Until Castro formally pardoned the pooch.

U.S. officials won’t have any such canine backup in Havana this week. But they are being cheered on by a letter from 78 former U.S. statesmen and others who favor President’s Obama’s normalization policy.

They include George Schultz – Ronald Reagan’s secretary of state – a man who knows a thing or two about ending cold wars.

Tim Padgett is WLRN's Americas editor. You can read more of his coverage here.