CIA Agent Got So Deep Undercover, He Became A Star As The Lead Singer Of A Band

So what exactly is a spy? Well, if you want to know, the best place to look probably isn’t at the movies. James Bond might be the most famous name in espionage, but he seems to have missed the “secret” part of secret agent. He visits all the most glamorous people and locations, and high drama follows him wherever he goes.

It’s funny because Bond’s creator, Ian Fleming, had been a spy. He’d started out as a journalist, which allowed him to visit Russia to report for U.K. newspaper The Times while also passing information about the country’s military strength to the British government. During WWII he joined Naval Intelligence and helped gather intel, disperse misinformation, and even advise the Americans on their own espionage efforts.

In today’s world, espionage tends to take one of two forms, but the overall goal is the same. You can use technology or the more traditional human resources, but the intent is to find information that wouldn’t otherwise be available to the public. Hack a computer or convince an official to turn traitor, and you could gain access to all kinds of state secrets.

Sometimes intelligence officers will be semi-official, such as when they’re attached to a diplomatic delegation. They may pretend to be journalists or businessmen. Others will be under deep cover, with whole new identities. There’s also a distinction between an agent, or person with access to information, and officer. Officers work for organizations such as the CIA to recruit agents who can help achieve their goals.

If you take a look at the CIA’s website, then you’ll see that lots of members don’t handle agents but are analysts, inventors, lawyers, or medical professionals among others. Not Darrell Blocker, who was an officer who knew how to recruit. In a talk in 2020, he said, “A person like myself is always looking for that anomaly, that person who doesn’t feel like they’re being listened to, that person who doesn’t feel like they fit.” He also went far beyond normal CIA procedure.

To learn about Darrell Blocker we first need to travel to Augusta, Georgia, where he spent some of his childhood. That was after moving around with his Air Force father, whose postings took him from Texas to Italy to Japan. That’s a pretty good way to develop an interest in foreign travel. Navigating different friendship groups and bringing people together also form a skill set that serves spies well, and Blocker learnt them on the playground.

Racial tensions still simmered in Georgia in the 1970s with segregation still a very recent memory. Blocker is black, but he still found a way to talk to white kids. He described his childhood as “fighting and juggling and cajoling and calling” to try and nudge some unlikely friendships into being between groups that would otherwise have stayed separate.

The Blockers were a church-going family, but Blocker had trouble with the kind of blind faith that Christianity seemed to expect of him. In another sign of how suited he was for his future career, he started asking questions and challenging authority. Parents and pastors equally were tired out by his refusal to just accept their answers.

Less obvious as a contributor to his spying success was his love of singing in the choir, which started at church, then continued through high school and college. Who knows what dangers he’d later face as a CIA operative in the field, but back then one look from Mrs. Mazyck the choir director was enough to stop him in his tracks. And it was more than discipline he’d learn from music.

His next stop after high school was the University of Georgia, where he spent some time at Shabbat dinners with members of AEPi. AEPi is a Jewish fraternity, and Blocker found himself drawn into a world where religious debate wasn’t just tolerated but encouraged. It would lead to his eventual conversion to Judaism many years later.

Again there were seeds of what would be Blocker’s career in his interest in Judaism. One story from the Torah that particularly attracted him was that of Joshua and Caleb. They were the men who gathered information on Canaan for the Israelites and were celebrated for it. In other words, they were spies.

When he’d finished his education, Blocker would follow his father into the Air Force for four years. He worked there as an analyst before turning to the CIA. It may or may not have been in 1989. Details on Blocker’s spying career are obviously not entirely public knowledge. We do know that his application essay was about Israel and Palestine and the Intifada.

Blocker may have traveled well in his childhood, but that was nothing compared to the 22 countries he would live in as an adult. The bulk of his work was in Africa, where he would participate in operations in Senegal and Uganda, but he also made trips to Europe and Asia. Eventually, he would even lead the CIA’s Africa division.

Now it was becoming clear just how far espionage could be from a life of glamour. Blocker saw brutal violence, including the genocide that would later be fictionalized in the movie Hotel Rwanda. He also witnessed the bloody Battle of Mogadishu, which inspired the film Black Hawk Down. His service in Somalia even won him a medal.

They called the Directorate of Operations in the CIA the clandestine service, and Blocker would finish his career there. He was the highest-ranking black officer in the department and oversaw the training of new recruits. He also managed to avoid much of the suspicion that would sometimes unfairly accompany Jewish officers.

An Israeli flag had hung upon Blocker’s wall in Senegal, and he formalized his conversion to Judaism a year before his retirement from the CIA. Some people might have tried accusing him of dual loyalties, but he thinks they were too distracted by his skin color to dwell on his religion. After all, there aren’t that many black faces serving as top American spies.

Blocker’s atypical background allowed him to occupy a space where not many people would fit. He actually saw it as a conversation opener, where, “There was always something going on in the world where maybe the position of being a Black man was at odds with what my government was doing or what my institution was doing.”

In all, Blocker’s CIA service lasted for 28 years, and by the time he retired, he was equal to a three-star general in rank. At that point, he may or may not have gone into private security, although he did re-emerge when his name was floated as a potential director of the CIA. He didn’t get the job, but more than one outlet picked up on his storied career, including his unexpected trip into celebrity.

He wasn’t exactly undercover as a rockstar. He’d traveled to Uganda in 2003 under the traditional guise of a representative of the State Department. But this was the boy who’d sung at high school and in glee at college. Of course he was going to jump at any chance to get involved in music in between all the clandestine ops.

An American guitarist, a Canadian guitarist, and a Scottish pianist walk into a club. No, it’s not the start of a joke, but the situation Blocker found when he was in Senegal in 1996. They were a talented group of instrumentalists, but they needed a singer, and he was happy to join them.

Every Thursday evening, a group of diplomats would relax in the British club in Dakar, and Blocker and his friends would provide live music. They were also available for house parties. It didn’t matter if you preferred Otis Redding or Hootie and the Blowfish, because they played it all. It was a good warmup for what would happen in Uganda.

Trip Advisor called Bubbles O’Leary’s “one of the best places to party in Kampala.” Blocker soon found his way to the club, and yet again his love of music became a basis for lasting friendship. In particular, an American guitarist called Jim Logan was performing on stage when he saw Blocker mouthing along with the lyrics.

Logan was a serious musician who had studied at Berklee College of Music, and was in Uganda as the husband of an embassy worker. On the plane, he’d met a British bass-player named Jim McGuigan, and the two had started jamming together. Ugandan locals Godfrey Lubuulwa and Dach Zziwa and Congolese musicians Ibrahim Kayenga and David Nsiluwaba soon joined them, and the Kampala Jazz All-Stars were born.

Now there was the opportunity for the band to gain a singer, and a man whom Logan would later describe as “a little bit of a smoky voice.” It was just the sort of sound they needed for their jazz covers. Blocker wasn’t quite so enthused. After all, he had important espionage work to do. But Logan managed to find a secret weapon when he approached Blocker’s wife.

She was the one who told Logan all of Blocker’s favorite songs so that the Kampala Jazz All-Stars could learn to play them. What a Wonderful World by Louis Armstrong was at the top of a 15-track list, and when Blocker learned what his friends had done, that was it. He immediately started playing with them.

What he didn’t expect was that they weren’t just going to be some minor covers band in a little club in Kampala. As word got round, the crowd at Bubbles O’Leary’s grew every time they were in there. The only performers doing better in Uganda at the time were a few big-name popstars. Their fame even spread into neighboring Kenya.

When Blocker had some time off, he did what anyone in a foreign country would do and took his family on a sightseeing trip toward the Kenyan border. They took ATVs out to the lake at Jinja and rested on top of a mountain. He was a little suspicious when a nearby woman started staring at him, but then she asked, “Are you in a band? In Kampala?”

She was thrilled when he said yes, even smacking her companion to emphasize, “I told you that was him!” It seemed Blocker had become a celebrity, which you’d think could be a hindrance to all the subtleties of spycraft. In reality, it would actually turn out to be quite the opposite. Blocker even thinks it may have helped him do his other work.

It wasn’t all plain sailing, with the hectic schedule of the band leading “to the point that it was starting to get in the way of the reason I was in Uganda.” He also had to keep lying to his bandmates and friends. They had to think of him as a random “something-something” embassy official, although Logan claims that he knew there must have been more to it because Blocker was so clever and so elusive.

Despite all those problems, it seems that Blocker did manage to find the advantages of his celebrity hobby. He thinks it may have even strengthened his cover story, at least with people who didn’t know him as well as Logan. He told ABC News in 2019, “My clandestine activities were enhanced by being viewed as a singer, because who would ever think that one could be both?”

So while Blocker was hiding in plain sight, it became possible for him to move outside of normal diplomatic functions. He specifically claimed to ABC News, “My singing expanded my circle of potential contacts to pursue.” And that was obviously a benefit to a man who had to “spot, assess, develop, and recruit spies.”

Not that the spy could talk to potential contacts willy-nilly. They might come into a gig and sit there in the audience, but Blocker couldn’t acknowledge them while he was up there pretending to be a casual singer. They were equally aware that they couldn’t talk to him publicly other than to appreciate the music.

It also seemed that Blocker’s CIA training was helping him improve his musical performances. The Kampala Jazz All-Stars had journeyed out into the Ugandan countryside to play a concert in Soroti. It was six hours from the capital, and they had 1,000 people waiting for them. Obviously, they wanted to make an impact, but it didn’t start well.

The people of Soroti just didn’t seem to enjoy the same songs that had made the band so popular in Kampala. There was no energy or enthusiasm in the audience and Logan didn’t know why “it just wasn’t hitting.” Luckily, figuring out how to connect with people and get them onside are key skills for a CIA recruiter.

Soon Blocker had come up with a plan of action, and it was actually pretty simple. “We’ve got to start doing stuff that they hear and they recognize.” That meant that rather than jazz standards, they turned to reggae. In particular, they struck up a Bob Marley tune that in moments would have that muted crowd dancing.

Blocker’s musical exploits in the CIA would continue even after he left Uganda and the Kampala Jazz All-Stars behind. Most often, that was as the man entrusted with the great honor of singing the national anthem. His distinctive tenor would fill at least eight different embassies with the familiar words of The Star-Spangled Banner.

Since then, Blocker has opened up further about the similarities between being a singer and being a spy. The particular word he likes to use to describe both roles is “intimate.” As he put it to ABC News, “If you are truly paying attention and listening to whoever is sitting across from you, they will know it, and they will know that you’re sincere.”

That’s true when you’re winning over an audience, and it’s equally true when trying to recruit an agent, although Blocker added, “Spying is easy; singing is hard.” He’s lucky in that he’s had the chance to do both and do both well. It’s one of the most fascinating aspects of an illustrious and decorated career.

So some spies may hide from attention, and others may court it. It seems that stepping out onto the stage may be a surprisingly effective way to turn a beloved hobby into a powerful tool of espionage. Who knows what other celebrities may be hiding secret careers behind an innocuous-sounding lie?