In global politics, some moments quietly reshape the future. Others arrive with unmistakable tension. As negotiations and strategic pressure mount across Latin America, new questions are emerging about the future of democracy in countries long defined by authoritarian rule.
On a recent episode of Breaking Battlegrounds, hosts Chuck Warren and Sam Stone were joined by foreign policy expert Carrie Filipetti to examine what negotiations, security concerns, and political reforms could mean for Cuba, Venezuela, and the broader Western Hemisphere. Their conversation highlighted not only diplomatic strategy — but also the human and security risks shaping U.S. policy.
Elections as a Condition for Change
Filipetti argued that any meaningful progress in negotiations should include a clear path toward internationally observed elections. Without democratic reform, she suggested, instability will continue to define the region. Authoritarian governance has fueled migration pressures, economic hardship, and geopolitical tensions that increasingly demand U.S. attention. Establishing credible electoral timelines, she said, could help lay the groundwork for long-term political stability — but achieving that goal will require sustained pressure and coordination.
Security Risks and the Legacy of Havana Syndrome
The discussion also turned to safety concerns involving American diplomats and travelers. Filipetti pointed to past incidents known as “Havana syndrome,” which left numerous U.S. officials reporting unexplained health effects during diplomatic assignments. She argued that accountability and protective measures must remain central to any future negotiations.
Beyond isolated incidents, the conversation emphasized broader intelligence and surveillance risks in authoritarian environments — including concerns about monitoring of foreign visitors and the role of state-controlled infrastructure. These issues, she noted, reflect deeper structural challenges that negotiations alone may not quickly resolve.
Regional Power Struggles and Global Influence
Another major theme was the interconnected nature of political regimes in Latin America. Filipetti described how alliances among governments in the region have shaped both domestic governance and international strategy. She warned that unresolved instability could allow outside powers to expand their influence in ways that directly affect U.S. interests.
At the same time, she emphasized that democratic traditions still resonate strongly among many citizens — particularly in Venezuela, where institutions and electoral processes have historical roots that could support reform. Cuba’s path, however, may be more complicated due to its longer history without democratic governance.
A Long Road Toward Reform
Despite the challenges, Filipetti expressed confidence that populations in both countries are capable of embracing democratic change. She pointed to the activism and political engagement of diaspora communities as evidence that democratic ideals continue to shape aspirations for the future.
Still, she cautioned that transformation will likely take time. Negotiations may represent only the first step in a broader effort to reshape political conditions across the hemisphere. As policymakers weigh strategic priorities and humanitarian concerns, the outcome of these debates could influence regional stability for years to come.
Transcript
Sam Stone: Carrie, shouldn’t one of the conditions that Donald Trump is putting in be that they’re be at some point for Venezuela, for Cuba, theoretically, potentially, eventually for Iran. It’s a timeline for an internationally observed or administered election.
Carrie Filipetti: Yes, I think that is essential. The other command that I would make of the Cuban regime, everybody forgets about this, but we had significant amounts of American diplomats that were injured inside Havana, Havana syndrome. We’re now hearing that that was likely a weapon that was created by the Russians, I’m not surprised. We know that they have that capability.
So we need to be holding the Cuban regime and the Russians accountable for this. There’s no way that the Russians deployed that against American diplomats without the regime giving them the okay. So looking into Havana syndrome, making sure that we’re protecting our citizens. If you visit Cuba, your hotel is run by the Cuban military. That means they are spying on you. And in fact, they have actually gotten long-term spies for the Cuban regime by going into people’s hotel rooms, reading their diaries and so on.
So this is something that they regularly do to antagonize Americans. So we need to make sure we’re protecting Americans in these negotiations. And we need to make sure that we’re moving towards internationally observed elections because again, the whole reason for the instability that is generating President Trump’s interest in our hemisphere is the fact that these are authoritarian, undemocratic regimes. And we won’t address that if we continue to see those regimes exist.
Just putting Delcey Rodriguez in power instead of Nicolas Maduro.
Sam Stone: When you mentioned going into the hotel rooms there, I had a flashback to 1987. I got to visit the Soviet Union with my family and the bathroom at our hotel had this giant blinking light camera in the ceiling.
Carrie Filipetti: That’s exactly right. know, I had heard this story and I don’t know how true this is, but they’re basically saying, you know, sometimes they would go into different facilities to check for bugs and they would find that the bugs were the actual infrastructure of the building. were actually in the actual physical structure. wasn’t just added. So the Cuban intelligence services are some of the most sophisticated that there are.
They’re the ones that were providing support to the Maduro regime. So these are very closely connected regimes. So it is critically important that we get rid of the Cuban regime, that we get rid of the Maduro regime, because that will allow us to focus our energies on things like China, which these two regimes have essentially been proxies for China in our hemisphere for many, years.
Sam Stone: Are those populations, I mean, do you, you’re closer to them certainly than we are. Are they ready to embrace a move towards capitalism? mean, fundamentally, do we have the sort of zeitgeist there that you’re seeing with the population in Iran to have something different happen?
**Carrie Filipetti: **I mean, well, let’s start with Venezuela. Absolutely. They had decades of democracy and they know all of those institutions. They know how to reform these institutions and they feel that democracy is really essential part of their heritage. Bolivar actually helped liberate many countries and bring democracy to those countries in Latin America. So this is something that is very well known to them and partially why I’ve always argued that getting rid of Nicolas Maduro is not going to result in an Iraq like situation because democracy is really native there and they know how to do it.
They actually organized their own primary elections in 2023 and so we know that they have the ability. Inside Cuba obviously they have been without democracy and it’s been many many many many years. They don’t have a legacy of democracy. It will be a lot harder. But you have seen so many different Cubans that have come to the United States, contributed heavily to the United States, understand the important role of democracy. I have never seen more pro-democracy activists and more inspired democracy activists than among the Cuban people.
You know remember Secretary Rubio, who is a huge proponent of democracy and virtue. He comes from a Cuban background. Senator Cruz comes from a Cuban background. So these are some of the people that are most connected to democracy. It’s going to take a lot of time. This is not going to be easy. I think this is why President Trump is trying to do the negotiation track for now. But certainly we know that both the Cubans and the Venezuelans are capable of it.
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