CIA? More Like CON | Investigation
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Welcome to True Spies. Week by week, mission by mission, you'll hear the true stories behind the world's greatest espionage operations. You'll meet the people who navigate this secret world. What do they know? What are their skills? And what would you do in their position?

This is True Spies. Espionage is all about building relationships with people and then manipulating them. It's exactly what con men do. And the Wayne Simmons story should go down in history as one of the most successful cons ever. This is True Spies. Episode 64, CIA or CON? Secrecy defines the lives of true spies.

CIA officers can live their entire career undercover.

Even their family may not know that they work for the CIA. So it's not unusual after 20, 25, 30 years for someone to say, "Okay, I'm retired now, and I'd like to share the fact that I was a CIA officer." But under the cloak of agency secrecy, there is fertile ground for deep deception. Tall tales can blossom here, unchecked and unprovable,

That is, unless you have a dogged true spy on your case. My name's Kent Clisby. I formerly served as a CIA operations officer. I also served as a contractor for the CIA running counterterrorism, counterintelligence and other operations throughout the world.

Kent started off with the CIA in 1994, but after five years, he hung up his employee status, but returned to work for the agency as a contractor in 2001, taking on a range of operational and training projects until the mid-2010s. But the path that led Kent to the CIA in the first place, well, that's not your usual true spy's origin story. Kent didn't grow up with a laser-focused ambition to become a spy.

In fact, he followed a winding and varied career path that took him all over the place. I had been a linguist in the military.

traveled the world teaching English as a second language, working in refugee camps throughout Southeast Asia, worked for the government in Saudi Arabia, taught in a university there, worked for a consulting company in the UK, and worked for them throughout Europe. It wasn't until his mid-30s that Kent decided to settle into the world of espionage.

But what drew him to the profession was not the allure of gadgets and glamour. No, his reasons were a little more practical. I needed health insurance really bad because I had a young child and the CIA offered me a job and they had great health insurance. Who would have thought that joining the CIA would be the family man decision? But once Kent was on board, his career was anything but pedestrian.

He worked in everything from narcotics to terrorism, from recruiting spies to training them. I was able to cram a lot of experience into a short period of time. And by the time Kent started to wrap up his final CIA contract around 2010, he'd accrued an extensive collection of contacts. So I had a wide network.

throughout the military as well as the civilian intelligence community. I'm always open to any kind of opportunities or networking. So when a former colleague said, "Hey, I've got a buddy who you really should meet. He's also an ex-agency guy and he's really cool." Kent was up for it. Yeah, absolutely. I drove up, met them in a restaurant.

Little did he know, but this lunch date would shape the next three years of Kent's life. So, time to meet the man at the center of this story. When you first meet Wayne Simmons, he was talkative, very boastful. He was always dressed in a suit and tie with an American flag. Right, that kind of guy.

As the outfit might suggest, Wayne Simmons wasn't keeping a low profile. He was a showman, someone who lapped up the limelight. So Wayne Simmons had been on Fox News for many years. I don't have cable TV and I never watched Fox News, so I had never seen him, but he was notorious or famous already.

Looking back at clips of his appearances, what he was known for and I guess what they wanted from him was belligerent sound clips

of a confident sounding person justifying the war on terror and justifying any kind of torture or any actions that would be taken against terrorists, they would get justification and support. You look at him now, he's just so ignorant. But at the time, his point of view was hugely popular.

Within the first three minutes of meeting Wayne, Kent knew something wasn't right. Even before the waitress came to take our order, Wayne started in with, "Hey, yeah, well, you know, us ops guys gotta stick together," or, you know, talking about drugs and big busts. In Kent's mind, it wasn't just a penny that dropped. It was more like a bomb.

Boom. Nothing rang true. It was just like red lights flashing, alarm bells ringing. Who does this dude think he is? Who does he think I am to not see through him? There's the saying, it takes one to know one. But in this case, we should say, it takes a true spy to sniff out a fake one.

And Wayne Simmons was playing a dangerous game. Simmons claimed he was an expert in the Middle East, in Islamic extremism, in counterterrorism. And these are all things that I actually am an expert in. I have lived and breathed them. So it didn't take long to spot the inconsistencies, the errors, the implausibility of the stories Wayne Simmons was spinning.

I've met and known hundreds, thousands of CIA and ex-CIA officers, and nothing he said was congruent with what a conversation between ex-CIA officers would have been. He was talking about busting narco traffickers in the Caribbean and

Yeah, took down X billion dollars worth of drugs. He was like a caricature of what an espionage operational officer would look like or sound like in a bad movie or a really cheap thriller. - A harsh diagnosis. Would you confront this man then and there? Call his bluff? It's tempting, isn't it? But Kent's a professional. - Of course, I didn't say anything.

Because playing your cards close to your chest gives you more options later down the line. Never a wise decision to act in the heat of a moment. For this moment was most definitely heated. Let me explain a little bit about my character. When I was young, I was very hot-tempered. I got in fights. I hurt myself in fights. I hurt other people in fights. I had a very quick temper. But as I have matured, I don't get angry.

The only thing that really makes me mad now is somebody trying to play me for a fool. That's exactly what Simmons was doing. Or trying to do. Kent was suspicious from the get-go. But not everyone is as scrupulous as our true spy here. He had obviously played many people for a patsy, many people for fools. He was a constant guest on a major media outlet.

And he was, in effect, representing the CIA. Every time he was on, he'd be represented as CIA counterterrorism expert, CIA intelligence officer, former CIA covert action operator with vast expertise. And Kent Clisby was having none of it. He had gotten in my face and, in effect, dared me to call his bluff.

So on the drive home after that lunch, I determined I'm going to find out who the hell is this guy. So I started doing kind of due diligence that I hadn't done before the meeting because I trusted my buddy, who now was clearly not trustworthy anymore. His judgment was very much compromised. Okay, so maybe this mutual friend should have been a little more discerning when it came to buying into Wayne Simmons' story.

But it's worth zooming out for a moment to see just how widely accepted the story was. Not only had Wayne Simmons convinced Fox News that he was ex-CIA, but he was also using the regular airtime to convince millions of people all over America and around the world that he had solid CIA credentials. And that's not all. Wayne Simmons even published a novel about a former operative called back to service for one last mission.

He claimed the book was based on his own experience, and guess what? On the back of the book, there's a blurb from the then US Secretary of Defense, Donald Rumsfeld. The blurb reads, Wayne Simmons doesn't just write it, he's lived it. Wayne Simmons hadn't just convinced the media, the public, and a few gullible characters in Kent Clisby's network. The story was accepted at the highest reaches of government, but Kent wasn't buying it.

I just had to confirm my gut instincts that had told me he was a fake and a fraud. By this point, Kent was out of the CIA. But even if he was still an agency employee, digging into top secret files would have been out of the question. That stuff is kept secret for a reason. And it's CIA policy not to confirm or deny claims like Wayne's. So Kent had to work the resources he had to hand.

Everything that I developed was completely from open source, from records, from people that were not classified at all. Kent begins with every true spy's most valuable source of intel, human assets. I first started working my network and working the network that Simmons was part of to get to the bottom of who Simmons was, how he got...

to the position he was in and what was going on here. I did extensive vetting, gathering details, keeping an eye on him, asking other people at all levels of the agency if they knew him, what they knew about him. While the alarm bells kept ringing for Kent, it felt like his concerns were falling on deaf ears.

I thought there would be a vigorous response, officially and unofficially, from former CIA officers as well as from the government agency itself. And there wasn't. But this was not the end of the road. Kent had an idea. At that time, there was a very...

public and vigorous campaign against what they call stolen valor. That is people claiming credit for military service, military decorations, military experience that they don't have. There was a pretty large network of military veterans that got really good at vetting claims.

They knew exactly how to work the bureaucracy to either confirm or refute someone's claims of military service. So as part of my effort, I thought, hey, you know, what Simmons is doing is stolen valor. It's CIA stolen valor.

So I approached the Stolen Valor military networks and suggested, hey, let's join forces here. And when they first heard about it, they were, whoa, cool. Yeah, no, this is great, man. Yeah, we can work together. This will be a really great extension of our existing efforts. And we'd love to work with CIA veterans to expose Stolen Valor cases. Send me what you got on Simmons and I'll get working on it.

Great, someone's finally listening. The ball is rolling. Or is it? Very quickly, they either went silent once I sent them information, or they came back and said, Simmons is who he says he is. We have no interest in this, period. And we're not going to be working on this. Something wasn't right. These Stolen Valor guys are relentless. I mean, they're pit bulls trying to get to the truth.

Something scared them when they looked into Simmons' background. Nobody would tell me why they were scared, and nobody could give me any kind of confirming information about what led them to believe that Simmons was real. What would you do in the face of such a shutdown? What if Wayne Simmons is legit after all? Is that why the query is shut down so fast?

"Do you persevere in your quest for the truth or walk away?" No prizes for guessing what Kent did. He carried on, of course. The reaction from the stolen valor network only made him more suspicious, more determined than ever. So he went back to plan A, working his personal network, and it began to yield results. My efforts were gaining traction among CIA veterans.

Kent reached out to former colleagues and new connections throughout the agency, sharing his assessment of Wayne Simmons and asking them to share theirs in return. I'll read you some examples here. These are what they sent me. I was at Fox about a year ago in the green room. He's never said a word that indicates real service.

This message went to Fox management and they were told that Simmons was not real and they risked great embarrassment if he continued appearing on the air. A month later, he was on the air again. He was on C-SPAN and he was commenting on Benghazi. It was weird beyond belief. From these responses, Kent knew he was not alone. Others suspected that Wayne Simmons was a fraud.

But to Kent's disappointment, no one within the CIA was willing to escalate the issue. None of them had really put any energy into exposing Simmons and ensuring that the fraud came to an end. Kent, on the other hand, was a bloodhound following a scent, and he was going to follow the stench of lies all the way to the source.

I didn't have much to lose. I wasn't on the CIA payroll. I wasn't getting a pension. I was more focused on doing the right thing than worried about blowback from bringing this issue up.

I was focused like a laser beam on proving he was not a CIA officer. A laser beam that would burn brightly, cutting deep through the layers of lies until there was nowhere left to hide.

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Kent Clisby was determined to expose Wayne Simmons as a fraud. I can tell you that for three years, I was researching him, vetting him, using my networks to do due diligence on him. So what I did is I put together kind of a short couple-page dossier of his claims. And the first place to look for those claims? From his website, his About Me, it's one paragraph.

His claims were that he had been 27 years working for outside paramilitary special operations group, that he was a CIA officer, that he was a non-official covered officer.

Kent shares the claims on Wayne's website with other legitimate CIA people in his network. All you have to do is a real agency officer read that one paragraph and they know this guy's fake. And I shared assessments from other actual CIA officers who had had interactions with Simmons. All the while, Kent keeps his investigation under wraps.

Because at the end of the day, he's a true spy using the true tradecraft of secrecy. I never shared with Simmons or our mutual friend that I thought he was a fraud. I kept in contact with him and Simmons always had some kind of, oh, I've got something coming up and it's going to be a big business and blah, blah, blah, blah, blah. You know, it was

always smoking mirrors about really cool things were gonna happen and he was high level and he was plugged in. - Wayne Simmons kept boasting and Kent kept listening, collecting more and more material for his investigation. And he continued to use his personal network to drill down into the truth.

I arranged an introduction to a couple of other ex-CIA officers. One specifically was very high level. He'd been one of my bosses when I was new in the agency and he had retired pretty much at the highest level that you can get. I introduced them and my friend was an avid Fox News junkie and he knew of Wayne, probably seen every time Wayne had ever been on TV.

And I had shared with my friend, call him Mr. X, I shared with Mr. X all of the details that I had discovered about Wayne. And it was very clear to him that Wayne was a fraud. So he started interacting with Wayne on social media.

He was very aggressive. He was like, dude, you're not who you say you are. I mean, he came right out and confronted Simmons. It was very interesting. Simmons went into a sort of admit nothing, deny everything, make counter accusations. But then the tide changed. Wayne knew the game was up.

After a couple of exchanges, he told my friend, I will never personally hold myself out as CIA again. Gotcha. Not only did Kent and his CIA friend have an admission from Wayne Simmons, but they had the admission in writing. So once we got that admission, that's when I wrote this article. That's right. Kent was going public with his suspicions.

He drafted an article detailing all of Wayne's far-fetched claims about his agency experience and offered evidence that they were bogus. And this confession from Wayne, it was the pièce de résistance, the cherry on the cake. It was gold. But there was just one final step to go before publication.

So as an ex-CIA officer, I have signed a secrecy agreement and anything that I publish has to be cleared by the agency. So they have a special committee that's set up before you publish something, you have to send it to them and they'll come back and they go, well, you know, page six, line three, don't say that, you know, and then you negotiate what you can and can't say. And then they'll finally give it the stamp of approval. So,

I drafted the article and sent it to that committee. Now, if in my article I'm exposing something classified, something secret, something covert, that there was this very deep, special outside paramilitary group that Simmons was a high-speed, low-drag member of,

In other words, if Wayne's claims about his CIA experience were real... Then the agency's official publication committee would have said, no, you can't publish that. In fact, you need to take his name out. You need to take out any mention of this special group if there had been any truth to Simmons' claims. The agency publication committee said, go for it. Good to go. You have our clearance.

Because of the way the CIA operate, they can't confirm or deny if certain individuals were or were not involved in CIA activities. So that was pretty much the only official support and or confirmation that I had for the claim that Simmons was a fraud.

So now I went to Simmons and said, "Wayne, I'm going to publish an article. I want to share it with you before I do. You're welcome to respond to it." And he retracted his confession in response to the article that I shared with him. He reiterated his claim that he'd been a CIA officer. Wayne Simmons was doubling down. He wasn't going to see his reputation pulled apart without putting up a fight.

In effect, he threatened me with retaliation. Here's what he says. "I categorically deny your accusations. For 27 years, I acted in the capacity of an operative for the CIA. I worked for the CIA. I have prepared a very intense response for you and your friend. It will be published shortly.

"You are publishing lies and you know them to be lies." That was his response. An intense response, it really was. Before Kent's article was even published, Wayne's threat began to materialize. I was totally shut down. This guy even has the power to silence the press. The press who, up to this point, Kent had been enjoying a decent relationship with.

When he'd initially sent his article out to a few media outlets, there was quite a bit of interest. It was received well. One had already pre-OK'd, "Yes, give us an article on Simmons, we'll publish it." But suddenly, it all changed. And they backed out. They refused to publish it. No media outlet would publish my article on Simmons.

Clearly, part of his very intense response was working. He and his network of people who bought his story denigrated me and my efforts. So if a tree falls in the woods and nobody's there, does it make a sound? Nobody heard what I had to say. Wayne continued appearing on Fox News. When is it time to call it a day? For Kent, this was it.

He tried to take his story to the government, to the agency, to the media. Nothing had worked. He packed up his files on Wayne Simmons and resigned himself to defeat. At this point, you've got to wonder, had it been worth all that trouble? Oh, yeah. Oh, definitely. My career has had many different facets. The only thing that is the constant throughout my career is that I do the right thing.

I have a clear conscience. And the people that did me wrong know that they've done me wrong. And I don't know if they can sleep at night or not, but I don't care. I did the right thing. Kent made peace with the whole thing and moved on. There's a song back in the 90s, I get knocked down, but I get up again. You ain't never going to keep me down. And that's me. And sure enough, a couple of years after Kent gets knocked down...

The case gets picked up again, this time by the FBI. Clearly I had come up in their investigation and I don't know how or why they began investigating him.

Is it because I stirred the pot? And, you know, I had been questioning him in many different areas, maybe. I don't know. They never told me. Either way, Kent was finally seeing the results he'd been pushing for all these years. A thorough expose of the life and lies of Wayne Simmons. And he was going to do everything in his powers to assist the investigation.

I shared all of the details I had, including his confession and then his retraction and his threats and that kind of thing. And finally, the truth was laid bare for all to see. So who is the real Wayne Simmons? He was a street dude from Annapolis, Maryland, a street-level hustler who had been involved in cocaine trafficking.

who had been involved in various street crimes. He was charged and convicted for a shooting incident, multiple driving under the influence arrests, multiple felony convictions. And as for his CV, well, it wasn't as illustrious as the About Me section on his website implied.

Here's a brief summary of Wayne Simmons' real career history. Bouncer at a nightclub, ran a hot tub business or something. But Wayne did in fact secure legitimate government jobs and contracts. What he tried to do was build on his notoriety and his fame as a Fox commentator.

by getting paying jobs with the government based on his connections and his notoriety as an expert. He was not accepted because of his expertise. He was not accepted because of any content he had to offer. He was accepted because of his name.

And it was these jobs that landed Wayne Simmons in the deepest trouble. So one of the things that he was convicted of was lying about his background for a security clearance. He had to fill out a standard security clearance form, and on that form, he said that he had worked for the CIA, and that was the crime that he was convicted.

The job that Wayne had lied to get was with the Department of Defense. In what they called back then the human terrain system, they needed some kind of on-the-ground cultural expertise in the areas that they were operating at that time. Afghanistan, Iraq. What the human terrain system did was

to engage mostly anthropologists. Sent them out as consultants, contractors into the field with the idea of understanding what's happening among the humans in the target area. Simmons was offered a job. I'm sorry, I can't hardly say it without laughing. It's hilarious in retrospect, but it's terrifying.

that they offered him a job and they hired him as a human terrain systems expert consultant. When you know his background, he had been a bouncer at a disco or a nightclub owned by an Iranian American. That was about his cultural expertise. But they hired him as a cultural expert and sent him to, I think, Afghanistan.

The scale of Wayne Simmons' con is almost unbelievable, and you have to give it to the guy. It was impressive. So, yes, I admire the savvy and skills that it takes to build such a criminal enterprise. As for the motivation behind the con...

Well, Kent has some theories there. I think bottom line is he had no marketable skills. He had an extensive criminal background. He had failed in multiple businesses. He had no future. He had no way of legally making money. What else was he going to do? Hey, they'll buy that I was a CIA officer. Yeah, go with it, man. Why not?

He carved out his own little niche and he was very successful at doing it. So I guess I can completely understand why he did what he did. The whole lie was the perfect way to explain away a lifetime of crime and professional failures. If anyone questioned the felonies and flops of his past, he could just tell them he was operating as an undercover CIA officer. It wasn't real. It's genius when you think about it.

How Wayne Simmons came up with the idea will never truly be known. But again, Kent has his own ideas on that. What I believe is that Wayne was a street punk. He was a thug. He was a loser from a good family. He was the black sheep of a good family. That part, at least, we know to be true. Wayne Simmons was from a high-flying military family.

His sister had held a number of high-ranking positions in the Defense Department and the Department of the Navy. His mother had been an FBI fingerprint analyst. As for the next bit, well, it's one theory. And I think that he was a snitch. I think he was a snitch for local and federal drug use.

The DEA, the State Bureau of Investigation, his local police. I believe that he was very likely providing them with information on the drug dealers and other criminal activities in his area. He's involved in the criminal activity and he agrees to provide information

to law enforcement in return for leniency in regards to his own involvement in criminal activity. And if that's true, then this experience would have equipped Wayne with deviousness and manipulation. Two skills that come in handy if you want to become a spy.

And even more handy if you want to pretend to become a spy. My guess was that somebody probably said, you know, what we're doing is just like the CIA. This is high-level espionage, buddy. I think somebody planted that in his mind and it grew into the story that he ended up portraying.

To this day, it's not clear how exactly Wayne Simmons first began to construct one of the most elaborate and effective cons in history. And as for the question of how he got away with it for so long, well, there's no concrete answers to that either. But again, Kent has a hypothesis. I don't have a smoking gun. There is no paper that says it.

It's very clear that he had what we call top cover in the bureaucracy. That is, somebody up above, somebody at high levels in the military bureaucracy was vouching for him and saying, Simmons is my boy. Don't touch him.

hire him, do whatever it is, get him in Fox, get him on the military's special journalist program. Kent believes that this would explain how Wayne was able to get away with such a brazen fraud for so long. If a con man has top cover, if a con man has trust of higher authorities, it just opens up everything up.

You know, the keys to the kingdom are at his disposal. No one can say for sure how Simmons was able to fool so many for so long. But one thing's for sure. His con was a dangerous one and had the potential to endanger national security and put American lives at risk. It all proved useful. All that work, all that due diligence.

None of it went to waste because in 2016, Wayne Simmons was convicted of two counts of major fraud against the United States. He was sentenced to 33 months in prison for his crimes. But what can we take from it all? Lessons from the Wayne Simmons story, I think the lesson is vet, vet, vet.

Vetting is doing due diligence and being absolutely certain of who you're dealing with and what their real background and expertise is. I'm Vanessa Kirby. Join us next week for another mission with True Spies.