Meredith Cavan’s entrance into the intelligence community started after she stole a glow-in-the-dark toy globe. She was a college kid who had gone to a career fair, vowing to grab as much free merchandise as possible. But after swiping the orb, she felt obligated to chat with the man behind the table of goodies. He was asking her questions about her background, and she had just studied abroad in the Palestinian territories and spoke Arabic. He asked for her resume, and though she had wanted to be a social worker or a musician, she handed it to him. A few months later, her only job offer came from the predecessor to the National Geospatial Intelligence Agency. She became an imagery analyst.
Meredith went on to the CIA, where she spent more than 20 years. And one of her jobs was as Southeast Asia Department chief, where she oversaw covert action, intelligence operations, and analysis across 30 countries. The years were 2021 to 2023, as terrorism was taking a backseat to strategic competition. Meredith’s priority was to thwart China’s influence and infrastructure in its most consequential playground.
One of her main jobs was to identify gaps in intelligence. It was the legacy of prioritizing counterterrorism after September 11th, even in that region. “For a long time, this was an area that we did not pay much attention to. These are tiny, bitty countries in the middle of the ocean. There was not a counterterrorism angle to them as much. But we realized that especially when you start looking at war plans, and how we would fight in a conflict vis-a-vis China, that Pacific area was really important.”
And so she had to establish new CIA bases in the region, something that not many intelligence officers have ever done. “There were places that were more receptive, and there were places that were less receptive,” she told me. “We ended up going to the places that were more receptive.”
I wanted to understand what the work would entail, especially in tiny, remote islands where flights land only so often. Meredith described a steep learning curve. “As someone that grew up in our Directorate of Analysis, I got a crash course in ‘So you want to build a new CIA office.’”
She described logistical challenges, from budgets to building materials to discussing what kinds of planes were best to travel island to island. “Everything that you need to make an organization run, whether it’s HR professionals or accountants or firefighters or building security people, we have all of those too… Except that [these] jobs are like ten times harder because oftentimes they have to do it secretly. They have to do it where the supply chain is not tracked back to us.”
She said the work paid off in dividends.
Those bases would help in another remit, intelligence diplomacy. “To quietly go and meet with the highest government officials and show them our intelligence.” It was a constant balance. “Anytime you’re doing intelligence releases on a one-on-one liaison foreign partner capacity, you’re balancing ‘What is the minimal amount of information that we could give that’s going to convey the point?’ … with the ‘How do we protect our sources and methods for the future?’”
The faulty intelligence on Weapons of Mass Destruction in Iraq was still a cloud, she said, though she noticed less of that in the countries she was assigned to. Sometimes, Meredith said, she just needed the analytic judgment and not the actual evidence derived from the human or signals intelligence.
Some countries still chose to work with China’s government or firms, she said. “A lot of these countries really didn’t have other options. It wasn’t ‘Go with Huawei or go with a similar priced thing that was available to you right now that you can implement,’ but it allowed them to write better contracts, ask better questions. If the Chinese wanted to establish a commercial port in your country, these are the questions that you should be asking.”
Intelligence diplomacy is not just about intelligence. It’s about building relationships. And Meredith — who is petite, chipper, and in Irish folk band with some other retired spies (plus a high school Spanish teacher) — operationalized her musical abilities.
“Southeast Asians and Meredith both love karaoke very much,” she asserted. “I have sung ‘Like a Virgin’ with an 80-year-old head of a Southeast Asian intelligence service.” I could just imagine them swaying and crooning.
Some may find it strange or infantile, but it’s about what happens when you hold that microphone to your lips. “When you're singing karaoke, you're vulnerable. You're singing Madonna with someone that has no business singing Madonna. And all of a sudden, people’s inhibitions aren’t there, and their willingness [shifts] to look at things from a different perspective.”
I diverted the conversation for a minute to confess my own scarring experience of attempting karaoke in Germany. And I mentioned how Frank Sinatra’s song “My Way” led to some karaoke singers reportedly being killed in the Philippines. Meredith said generally the most senior men get first dibs on that song. And that her grandmother grew up next door to Frank Sinatra, her great-grandmother actually delivering him when his mother suddenly went into labor.
I asked her about countries in the region that didn’t play so well with Washington during her tenure leading the Southeast Asia Department. Myanmar and the military coup in 2021. When Rodrigo Duterte turned the Philippines toward China, while arranging extrajudicial killings to curb crime. Was it hard to build trust with these officials? Did the trust go both ways? She said, “One of the beauties of the CIA is because we’re quiet, because we’re able to engage behind the scenes, we’re often able to keep the channels open and the discussions happening even with partners that are politically untenable.”
This week, North Korea fired a barrage of ballistic missiles into waters east of the Korean Peninsula, and President Donald Trump wants to meet with Kim Jong Un this year. By coincidence, I had also asked Meredith about how she helped to plan the very first meeting between Trump and Kim in 2018 in Singapore. “It was a crazy time to be the Chief of Korea Analysis at the CIA,” she said.
They were trying to lay the groundwork for that meeting by arranging a secret meeting between CIA Director Mike Pompeo and Kim — which media outlets learned about the following week and Trump confirmed by tweet.
“We’re quietly supporting these back-channel discussions about everything from the logistics of how to make [the Pompeo-Kim meeting] work and how to keep that quiet to, ‘Okay, so if the CIA director is going to meet with the North Koreans, what should he be talking about? What are the North Koreans most likely to bring up at this conversation? What are they hoping to get out of it from a leadership perspective on their end? What are red lines that they’re not going to cross?’ So, I had half my analysts dealing with [Trump’s threat to Pyongyang of] ‘fire and fury’ and the other half quietly supporting this other effort.”
We sat down together in July, a few days after China tested a long-range ballistic missile in the South Pacific. It came hours after Australia signed a security agreement with Fiji. “What it could mean is that from inside the First Island Chain, that they could launch a missile that might be able to hit the continental United States. I think one of the things that they're trying to show here is, ‘We are a nuclear power, and we are acting like a nuclear power acts.’”
I asked if China was taking a backseat the CIA, in the face of the war with Iran and Russia’s ongoing war on Ukraine. “I'm proud of what we did. I think we've accomplished a lot,” she told me. “I think there’s a lot more to do.”
Episode length: 40 minutes
Listen: On Spotify | On Apple Podcasts
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